TABLE OF CONTENTS

UNITED STATES


SECURITIES AND EXCHANGE COMMISSION


Washington, D.C. 20549

SCHEDULE 14A



Proxy Statement Pursuant to Section 14(a) of the


Securities Exchange Act of 1934


(Amendment No.  )

Filed by the Registrant x

Filed by a Party other than the Registrant o

Check the appropriate box:

o

Preliminary Proxy Statement
o

Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))
x
Definitive Proxy Statement
o

Definitive Additional Materials
o

Soliciting Material under §240.14a-12

graphic
UPWORK INC.


(Name of Registrant as Specified In Its Charter)



(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check the appropriate box)all boxes that apply):

x
No fee required.
o
 ☐
Fee paid previously with preliminary materials.
 ☐
Fee computed on table below per Exchange Act Rules 14a-6(i)(1) and 0-11.
(1)Title of each class of securities to which transaction applies:
(2)Aggregate number of securities to which transaction applies:
(3)Per unit price or other underlying value of transaction computed pursuant to Exchange Act Rule 0-11 (set forth the amount on which the filing fee is calculated and state how it was determined):
(4)Proposed maximum aggregate value of transaction:
(5)Total fee paid:
oFee paid previously with preliminary materials.
oCheck box if any part of the fee is offset as provided by Exchange Act Rule 0-11(a)(2) and identify the filing for which the offsetting fee was paid previously. Identify the previous filing by registration statement number, or the Form or Schedule and the date of its filing.
(1)Amount Previously Paid:
(2)Form, Schedule or Registration Statement No.:
(3)Filing Party:
(4)Date Filed:

2021
Annual Meeting of
Stockholders and
Proxy Statement


TABLE OF CONTENTS

Our mission is
to create economic
opportunities so people
have better lives.

graphic


TABLE OF CONTENTS

graphic

MESSAGE FROM OUR PRESIDENT AND CHIEF EXECUTIVE OFFICER


To Our Stockholders:

2020Fellow Stockholders,

Upwork—the world’s work marketplace—and the broad range of businesses and professionals we serve experienced tremendous growth and evolution in 2022. Through the waning phases of the COVID-19 pandemic, the violent outbreak of the ongoing war in Ukraine, and countless other threats to business continuity and stability of the global economy, we’ve remained steadfastly committed to reshaping how, where, and with whom the world works. That momentous progress led to full-year 2022 Gross Services Volume (GSV) of $4.1 billion (16% year-over-year growth) and revenue of $618 million (23% year-over-year growth).
Commitment to Innovation
In 2022, we embarked on several key innovation initiatives that supercharged the more than $3.8 billion of work that took place on our platform over the course of the year. Among them was an unprecedented year. COVID introduced a previously unthinkable level of uncertainty, but it also made one thing crystal clear: our collective norms around work would not,development and could not, ever be the same again. The pandemic drove everyone to reevaluate “where, when, and how” work gets done. I’m proud of what Upwork accomplished in 2020 and am excited to highlight sometesting of our successes.

Equipping Our Teamnew end-to-end solution that makes full-time work arrangements an option for all our customers for the first time. This solution brings to Thrive

Atbear the onsetexpertise, experience, and technology that we’ve been honing over time to help clients easily and quickly find, vet, hire, onboard, and pay talent from over 165 countries across more than 10,000 skills who are interested in full-time opportunities. That vetting process also allows both talent and clients to “try out” a contract-to-hire working relationship before they commit to a full-time engagement.

We also added to our already robust Enterprise Suite by releasing talent performance and user activity reports alongside multi-approver, team-based approvals that support large-scale and complex workflows endemic to our largest clients. For shorter-term work engagements, we improved Project Catalog with Consultations (paid sessions designed to share expertise or outline the scope of the pandemic, our management team acted quicklya project), Project Tiers, and Catalog On Demand.
And finally, to protect the safety and well-beingdrive awareness of our team members (both full-time employees and freelancers). While many were already working remotely,innovative offering, we provided additional productivity and collaboration resources and enhanced and promoted programs to support everyone’s physical, financial, and mental health.

Strong Operational and Financial Performance in 2020

2020 acceleratedoriginated the emergence of a new era of work. This new era is unbound by the limitations of the old fully on-site full-time employee model and moves beyond the shallow nature of fly-by-night gig work. In this new era, remote freelancers and their clients—businesses large and small—work together seamlessly in trusted working relationships, experiencing greater adaptability and control, changing the trajectory of many careers and companies for the better. Because of the efficiencies and network effects created by our work marketplace, in 2020 we saw workers of every skill level and in every domain doing work they are passionate about while building thriving independent careers.accolade-winning “This Is How We witnessed companies permanently change their operating models and actively build Virtual Talent Benches of trusted remote freelancersWork Now” brand campaign that they returned to over and over again, allowing them to quickly scale up or down their teams.

Upwork is at the epicenter of this new work era, and this helped us achieve record performance in 2020 across virtually all of our key financial metrics. Our gross services volume, or GSV,1 and revenue increased substantially in 2020, achieving the highest growth rateslaunched in the fourththird quarter of any quarter since Upwork became a public company. This was a notable outcome, underscoring that the market opportunity before Upwork2022 and is huge—we believe it is in excess of $1 trillion—and continues to grow. We continued to demonstrate in 2020 that we are agile, innovative, andcarrying us well positioned to continue to lead the market in our space.

I continue to see a future that is rich with possibility for clients and remote freelancers on our work marketplace. The customers I speak with every day share incredible stories of the successes they find through our platform and the transformational moments they experience due to Upwork. And the broader statistics tell the same story: 60% of workers who gave remote freelancing a try in 2020 say that there is no amount of money that would convince them to take a traditional job. What’s more, a survey of Upwork clients found that 79% of those who increased remote freelancer hiring during the past year said that the increase was permanent.

1“GSV” represents the total amount that clients spend on both our marketplace offerings and our managed services offering as well as additional fees we charge to both clients and freelancers for other services. For additional information on gross services volume, please see page 57 of our 2020 Annual Report on Form 10-K for the year ended December 31, 2020.

into 2023.

As the world��s largest work marketplace that connects businesses with remote freelancers, as measured by GSV, we benefit from a virtuous cycle that drives scale and strengthens our competitive advantage. As we continue into 2021, our team is laser-focused on continuing to expand our customer impact by innovating, scaling, and evangelizing Upwork as the work marketplace for the world.

Our Commitment to Diversity, Inclusion, and Belonging (DIB)

Upwork’s mission

At Upwork, we believe in the maxim that “while talent is equally distributed, opportunity is not.” Helping organizations to build remote-first global teams is an integral part of our business model, and vision demandit is also the blueprint for how to build more diverse, inclusive, resilient workforces.
Our own hybrid workforce consists of roughly 70% independent talent located across more than 90 countries and over 700 cities around the world and reflects a multitude of backgrounds and cultures. Accordingly, we treat our diversity, inclusion, and belonging (DIBs) initiatives as top business priorities, as our team members deserve to be part of an Upwork culture and community that we cultivate anvalues, includes, and celebrates them. We are exceptionally proud that Upwork was again recognized for this commitment in this year’s Bloomberg Gender-Equality Index.

TABLE OF CONTENTS

Our eight Upwork Belonging Communities (UBCs) create spaces for team members who identify as LGBTQ+, Black, Hispanic/Latino/a/x/e, Pan-Asian, veterans, women, caregivers, and/or neurodiverse. We also founded UPstanders in 2022, a program open to all employees and hybrid team members offering workshops to build inclusive culturepractices, master authenticity, and disrupt bias throughout the organization and our operations.
We’ve further focused on creating internal communities and growth and development opportunities for our team members remote freelancers,of color, including GlowUp, for leaders of color; RiseUp, an internal sponsorship program; and Our Place, for senior Black women leaders. We've also partnered externally with McKinsey for their clients. PriorManagement Accelerator and Leadership Essentials programs as well as with Korn Ferry-facilitated Leadership U to 2020,further support and accelerate the careers of historically underrepresented groups. And, we were already onremain committed to diverse hiring practices by implementing a strong pathDIBs Health Scorecard and other mechanisms to building a diverse and inclusive team and culture at Upwork. Dr. Erin Thomas, PhD, joined us in 2019 as VP, Head of Diversity, Inclusion and Belonging asbetter understand the next step in our journey to build a company that was inclusive at the core, not as an afterthought. In 2020, we furthered our commitment to racial equality and social justice—demonstrated through our public action plan against racism, cultural competence training addressing strategies for amplifying Black employee voices, and guidance on cultivating an antiracist company culture to help other companies elevate the voices of Black employees. We began collecting diversity and inclusion data from new and existing vendors and incorporating inclusive sourcing into our procurement program. We developed and executed on our people strategy to build a more robust DIB infrastructure, which included elevating and evolving existing DIB programs such as our employee resource groups and applying a more rigorous DIB approach to all stages of our talent lifecycle. I was gratifiedpipeline.
Commitment to seeGlobal Community and Disaster Response
Amid geopolitical unrest, specifically during the tremendous levelongoing devastating war in Ukraine, we are proud of support and engagement acrosshow our company supported our team members for these efforts,in the impacted region, ensured customers had information and support to navigate this crisis, and showed up in a way that is consistent with our values.
We are particularly grateful to our Enterprise clients and partners who have participated in our Opportunity Unlimited program to hire professionals displaced by this war and help talent impacted by future conflicts get connected to the commitmentresources they need to allyshipwork from wherever they find themselves. In 2022, nearly 80,000 professionals working on Upwork who are currently based in Ukraine or who were forced to relocate to other locales due to the war have collectively earned more than $200 million on our platform. We are committed to serving our global community of customers and DIB work that Upwork employees demonstrated throughout the year. These values and concrete action plans are essential and are being embraced at every level of our company, including among our board of directors, as the nominating and governance committee oversees corporate responsibility and sustainability, including our ESG task force.

In addition to these internal initiatives, we made significant financial contributions to organizations that support the Black community and tackle the systemic issues that lead to Black impoverishment, unequalproviding access to opportunity, unfairopportunities and violent policing, and other social injustices. Upwork was also one of the first organizationslivelihoods not just in good times, but especially through unprecedented hardship.

Commitment to join the Stop Hate for Profit advocacy campaign, which called for advertisers to pause Facebook advertising in the month of July over concerns of the spread of hate and misinformation on its platform.

Our commitment to racial equality and social justice extends toEnvironmental Sustainability

In 2022, we solidified our board of directors. Since going public in 2018, we’ve added three new directors—and today, four of our eight directors are women and three directors are from underrepresented communities.2 In November 2020, we welcomed Anilu Vazquez-Ubarri to our board of directors. As the Chief Human Resources Officer of TPG Global,role as a global private investment firm, Ms. Vazquez-Ubarri contributes to our board of directors’ expertise in human-resources-related topics and is known for her well-established work in diversity, equity, and inclusion. Our board of directors’ recruitment efforts moving forward will continue to prioritize both key competencies and diversity, ensuring our directors’ collective skills and expertise squarely align with Upwork’s values, business, and evolving strategic priorities.

Our Climate Commitment: Carbon Neutrality

We have observed the growing interest among our stockholders and other stakeholders in better understanding how Upwork can help reduce environmental impact. We see our ability to impact climate change as twofold: through our unique business model that inherently keeps vehicles off the road by facilitating remote work for our large and growing customer base, and through our own commitment to carbon neutrality.

In 2020, we expanded our ESG disclosure by publishing an Emissions Report that details how we are reducing greenhouse gas emissions caused by daily commuting as well assustainability leader by reducing our facility footprint. Scope 1 and 2 emissions to only 15 metric tons of CO2e, maintaining our carbon-neutral operations, and expanding our Scope 3 analysis to include emissions from remote work, which we view as imperative given our remote-first workforce model. This allows us to set strategies to reduce and offset emissions from our team members’ remote work and support a more sustainable future of work.

We also continued to report in alignment with the recommendations of the Task Force on Climate-Related Financial Disclosures (TCFD) and submit our emissions data to CDP, earning a B score for 2022, which places Upwork in the top quartile of companies in our industry.
Commitment to Responsible Growth and Creating Economic Opportunity
Our distributed workforce model, which includes both employeeslongtime mission has been to create economic opportunities so people have better lives, and, independent talentas we reiterated throughout 2022, our corporate strategy is to innovate, evangelize, and scale the world’s work marketplace to be able to offer those opportunities even more widely across the globe. Workforce and product innovation along with bringing even more jobs from globally recognized enterprise brands to the platform are key drivers of that opportunity creation. In parallel, we engage for a variety of internal projects, helped us achieve carbon neutralityunderstand that growth and continued evolution must be steeped in 2019scalability, corporate social responsibility, sustainability, and 2020,accountability toward our stated near-term and we are committed to maintaining this position going forward.

In closing,longer-term profitability targets. I wantwould like to thank our Board of Directors for being incredible partners and a strategic asset to our company and our stockholders. The Board has been deeply engaged in oversight and working with me and the management team to navigate risks and opportunities, charting the future direction of our company.

Thank you for your continued support.

support of our mission, strategy, global community, and business.
Sincerely,
graphic
Hayden Brown
President & Chief Executive Officer

Hayden Brown
President and Chief Executive Officer

TABLE OF CONTENTS

2 Under California law AB 979, an individual from an underrepresented community is defined as “an individual who self-identifies as Black, African American, Hispanic, Latino, Asian, Pacific Islander, Native American, Native Hawaiian, or Alaska Native, or who self-identifies as gay, lesbian, bisexual, or transgender.”

graphic

April 20, 2021

28, 2023

To Our Stockholders:

You are cordially invited to attend the 20212023 Annual Meeting of Stockholders of Upwork Inc., which we refer to as the Annual Meeting. The meeting will be held exclusively online via live webcast on Tuesday,Friday, June 1, 2021,9, 2023, at 8:00 a.m. Pacific Time. The meeting can be accessed by visiting www.virtualshareholdermeeting.com/UPWK2021,UPWK2023, where you will be able to listen to the meeting live, submit questions, and vote online. We believe that athe virtual stockholder meeting provides greater access to those who may wantformat makes it easier for stockholders to attend and provides a safer forumparticipate fully and equally in light of the ongoing COVID-19 pandemic, and therefore we have chosen this over an in-person meeting.Annual Meeting. This approach also lowers costs, enables participation from our global community, and aligns with our broader sustainability goals.

The matters expected to be acted upon at the Annual Meeting are described in the accompanying Notice of Annual Meeting of Stockholders and proxy statement.Proxy Statement. The Annual Meeting materials include the notice, proxy statement,Proxy Statement, and annual report to stockholders, each of which has been furnished to you over the internet or, if you have requested a paper copy of the materials, by mail.

Your vote is important. Whether or not you plan to attend the Annual Meeting, please cast your vote as soon as possible by internet, by telephone, or if you received a paper copy of the meeting materials by mail, by completing and returning the enclosed proxy card or voting instruction form in the postage-prepaid envelope to ensure that your shares will be represented. Your vote by written proxy will ensure your representation at the virtual Annual Meeting regardless of whether or not you attend the meeting. Returning the proxy does not affect your right to attend and to vote your shares at the virtual Annual Meeting.

Sincerely,
Thomas Layton
Chairperson of the Board of Directors

Sincerely,
graphic
Thomas Layton
Chairperson of the Board of Directors
IMPORTANT NOTICE REGARDING THE AVAILABILITY OF PROXY MATERIALS FOR THE ANNUAL MEETING TO BE HELD ON TUESDAY,FRIDAY, JUNE 1, 2021:9, 2023: THE PROXY STATEMENT AND ANNUAL REPORT ARE AVAILABLE AT

www.proxyvote.com

www.proxyvote.com

UPWORK INC.

PROXY STATEMENT FOR 2021 ANNUAL MEETING OF STOCKHOLDERS

TABLE OF CONTENTS

Table of Contents
Page
9
10
INTERNET AVAILABILITY OF PROXY MATERIALS10
GENERALIMPORTANT INFORMATION ABOUT THE ANNUAL MEETING10
Record Date; Quorum10
Voting Rights; Required Vote10
Recommendations of Our Board of Directors on Each of the Proposals Scheduled to Be Voted on at the Annual Meeting12
Voting Instructions; Voting of Proxies12
Expenses of Soliciting Proxies13
Revocability of Proxies13
Voting Results13
13
14
14
15
15
15
16
16
17
18
18
19
19
19
19
20
20
24
24
24

PROPOSAL NO. 1 ELECTION OF DIRECTORS26
26
28
40

TABLE OF CONTENTS

Page
42
43
EXECUTIVE COMPENSATION45
45
72
73
74
75
76
77
78
79
81
82
82
82
83
84
84
84
84
85
“Householding”—Stockholders Sharing the Same Last Name and Address85
OTHER MATTERS87

B-1

TABLE OF CONTENTS

Forward-Looking Statements

This Proxy Statement for the Annual Meeting, which we refer to as this Proxy Statement, includes forward-looking statements. All statements contained in this Proxy Statement, other than statements of historical fact, are forward-looking statements. These statements are not historical facts and are based on current expectations, estimates, and projections about our industry, management’s beliefs, and certain assumptions made by management, many of which, by their nature, are inherently uncertain and beyond our control. Accordingly, we caution you that any such forward-looking statements are not guarantees of future performance or events and are subject to risks, assumptions, estimates, and uncertainties that are difficult to predict. For a discussion of some of the risks and important factors that could affect our future results and financial condition, see “Risk Factors” in our Annual Report on Form 10-K for the year ended December 31, 2020.

2022 and our subsequently filed Quarterly Reports on Form 10-Q.

TABLE OF CONTENTS

graphic
Proxy Summary

PROXY SUMMARY

This summary highlights information contained elsewhere in this Proxy Statement. This summary does not contain all of the information that you should consider, and you should read the entire Proxy Statement carefully before voting.

References to our website in this Proxy Statement are not intended to function as hyperlinks, and the information contained on our website is not intended to be incorporated into this Proxy Statement. In this Proxy Statement, we refer to Upwork Inc. as “Upwork,” the “Company,” “we,” “us,” or “our.”

Proposals to Be Voted On and Board Voting Recommendations

No.ProposalBoard
Recommendation
Page
1Election of three Class III directors named in the accompanying proxy statement

FOR

(ALL NOMINEES)

28
    
2Ratification of the appointment of PricewaterhouseCoopers LLP as our independent registered public accounting firm for 2021 FOR39
    
3Advisory vote on named executive officer compensation (“say-on-pay”) FOR41

Proposal
Board
Recommendation
Page
1
Election of two Class II directors named in this Proxy Statement
1a. Leela Srinivasan
graphic   FOR
1b. Gary Steele
graphic   FOR
2
Ratification of the appointment of PricewaterhouseCoopers LLP as our independent registered public accounting firm for 2023
graphic   FOR
3
Non-binding advisory vote on named executive officer compensation, which we refer to as Say-on-Pay
graphic   FOR
4
Approval of Restated Certificate of Incorporation to reflect recently adopted Delaware law provisions regarding officer exculpation and to make certain other technical and administrative changes, each as reflected in the Restated Certificate of Incorporation and described in the Proxy Statement
graphic   FOR
Key 20202022 Business Highlights

Upwork

Our mission is changing the way work gets done by placing independent talent at the heart of every business. Upwork operatesto create economic opportunities so people have better lives. We operate the world’s largest work marketplace that connects businesses with independent talent from across the globe, as measured by gross services volume, which we refer to as clients, with independent talent, as measured by GSV.

Despite the challenges of the COVID-19 pandemic, in 2020GSV.1

In 2022, we launched a new generation of executive leadership and generated strong operational and financial results while advancing valuable strategic initiatives. Key business highlights include:

Performance Highlights
Growing Our Work Marketplace
GSV grew to $4.1 billion, a 16% year-over-year increase
Generating Strong Growth
Generated more than $618 million of revenue, a 23% year-over-year increase
Expanding Our Active
Client Base(1)
Expanded the number of active clients by 6% year-over-year to approximately 814,000(2) while increasing GSV per active client 10% year-over-year to $5,045 in the fourth quarter of 2022
(1)
We define an active client as a client that has had spend activity on our work marketplace during the 12 months preceding the date of measurement. GSV per active client is calculated by dividing total GSV during the four quarters ended on the date of measurement by the number of active clients at the date of measurement.
1
“GSV” represents the total amount that clients spend on both our marketplace offerings and our managed services offering as well as additional fees we charge to talent for other services. For additional information related to how we calculate GSV, see page 49 of our Annual Report on Form 10-K for the year ended December 31, 2022. Independent talent on our work marketplace, which we refer to as talent, includes independent professionals and agencies of varying sizes, and is an increasingly sought-after, critical, and expanding segment of the global workforce. We define clients as users that work with talent through our work marketplace, and we refer to clients and talent together as users.
graphic2023 Proxy Statement 1

TABLE OF CONTENTS

(2)
As of December 31, 2022.
Strategic Highlights
Launching a New Generation of Leadership
Continued to invest in 2020, Hayden Brown was appointed asthe top talent necessary to drive our President and Chief Executive Officer, Jeff McCombs joined as our Chief Financial Officer, and Sam Bright joined as our Chief Product & Experience Officer.long-term success

Growing Our
Innovating the Work Marketplace
Developed an end-to-end solution that makes full-time hiring easily available to all clients

Launched Project Catalog Consultations and Project Tiers, Contract Workroom, MyStats, a Rate Calculator, enhancements to our GSV grewEnterprise Suite, and paid promotional products such as Availability Badges and Boosted Proposals

Announced a partnership with Credly, a leading digital credential platform, to over $2.5 billion,expand the number and breadth of certifications that can be verified on Upwork
Evangelizing the Work Marketplace
Increased our investment in brand marketing, underscoring our conviction that this is a 21% year-over-year increase.moment in time in which we can influence users meaningfully. In 2023, we plan to reduce our investment in brand marketing given our efforts to become more efficient in the current macroeconomic environment

Launched our new campaign, “This Is How We Work Now,” with the goal of helping companies realize that “whom” you work with is a much more powerful work transformation than “where” work gets done

Also launched Upwork Academy to help improve and diversify the skill set of talent on the platform and announced Opportunity Unlimited to connect professionals displaced from Ukraine with remote work opportunities

Scaling the Work Marketplace
Generating Strong Growth—we generated $373.6 million of revenue, a 24% year-over-year increase.

Expanding Our Core Client Base1—we expanded
Increased the number of our core clients to over 145,000, while maintaining client spend retention2 of 102% as of December 31, 2020.

1 We define a core client as a client that has spent in the aggregate at least $5,000 since it began using our work marketplace and also had spend activity during the 12 months preceding the date of measurement.

2We calculate client spend retention by dividing our recurring client spend by our base client spend. We define base client spend as the aggregate client spend from all clients during the four quarters ended one year prior to the date of measurement. We define our recurring client spend as the aggregate client spend during the four quarters endedspending $1 million or more on the date of measurement from the same clients included in our measure of base client spend.

Launching and Expanding Initiatives to Drive Growth—we announced Project Catalog (pre-defined, ready-to-purchase projects) and expanded Direct Contracts (enabling invoicing and billing for hourly work).

Establishing Strategic Partnerships—among others, we announced a partnership with Zoom that integrates Zoom’s video and voice communication tools into our work marketplace.marketplace by 45% compared to 2021

By doing this, we are establishing a strong foundation on which to capture the long-term value opportunity of enterprise sales and will continue to invest wisely and strategically to capitalize on that opportunity

We monitor GSV as a key financial and operational metric to evaluate our business, measure our performance, identify trends affecting our business, formulate business plans, and make strategic decisions. GSV is an important metric because it represents the amount of business transacted through our work marketplace. Moreover, we believe revenue is the primary measure of the performance of our business, as it provides comparability against competitors and is aligned to our strategic focus on growth objectives.
graphic
2 2023 Proxy Statement graphic

TABLE OF CONTENTS

Stockholder Value Creation

Driven byEngagement

graphic
Source: Capital IQ; representing percentage of outstanding shares as of January 17, 2023, based on the latest ownership filings.
Our board of directors and executive management team value feedback from our strong financial and operational performance in 2020,stockholders. In addition to our normal-course investor relations activities, we generated stockholder returns significantly exceeding thoseregularly engage with our stockholders on topics including our strategy, the composition of the broader market (based onboard of directors, corporate governance, and environmental, social, and governance, which we refer to as ESG, practices. In response to the decline in support for our Say-on-Pay vote at our 2022 annual meeting of stockholders, our board of directors and management team led a comparison vs.dedicated effort in the NASDAQ Composite Index)second half of 2022 to engage with our largest stockholders to discuss topics related to our executive compensation program in addition to our regular engagement topics.
We contacted stockholders representing approximately 43% of our shares outstanding and overall technology sector (based onengaged in discussions with stockholders representing approximately 23% of our shares outstanding. Members of our board of directors, including the NASDAQ 100 Technology Index).

The following charts show comparisons from October 3, 2018 (the date our common stock commenced trading on The Nasdaq Global Select Market) through March 31, 2021 and January 1, 2020 (the date on which Ms. Brown became our President and Chief Executive Officer) through March 31, 2021,chairs of the cumulative total returnscompensation committee and the audit, risk and compliance committee, which we refer to as our audit committee, and management team participated in these engagements and used feedback heard from stockholders as a key input in deliberations on our strategy, governance, executive compensation, risk management, and ESG priorities. Key themes from our engagement with stockholders and the actions our board of directors took in response include:

Key Themes
What We Heard from Stockholders
What We Did in Response
Executive Compensation
• Stockholders were broadly supportive of the increase in the percentage allocation of performance stock unit, which we refer to as PSU, awards in our long-term
incentive program
• Stockholders expressed varying views on the CEO Performance Award2 granted in
2021
• Notably, most stockholders appreciated the CEO Performance Award’s rationale and the rigorous metrics underlying it. No stockholders requested that we revise or
modify the CEO Performance Award
• Some stockholders who voted against our Say-on-Pay proposal in 2022 cited the CEO Performance Award as the primary reason for their opposition
✔ The compensation committee determined that the target number of PSUs that comprise our Named Executive Officers’ long-term incentive opportunity should represent at least half of their total long-term incentive
opportunity
✔ As a result, we increased the percentage allocation of PSUs in our long-term incentive program for our Chief Sales Officer to 50% for 2023, up from 40% in 2022. We maintained the allocation at
60% for our CEO
✔ The compensation committee expressed that it does not expect to make awards similar to the CEO Performance Award a regular feature of our executive compensation program
2
We define the CEO Performance Award as the performance-based option award granted to Ms. Brown in January 2021.
graphic2023 Proxy Statement 3

TABLE OF CONTENTS

Key Themes
What We Heard from Stockholders
What We Did in Response
ESG and
Sustainability
• Stockholders were enthusiastic about the progress to date, including our use of the IFRS Foundation’s Professional & Commercial Services and Software & IT Services industry standards (formerly known as SASB) and Task Force on Climate-related Financial Disclosures (TCFD) recommendations and our
disclosure of EEO-1 data
• Stockholders complimented the strong disclosure in our annual Impact Report and proxy statement
✔ We have decreased Scope 1 and 2 emissions to nearly zero and are currently evaluating the feasibility of developing SBTi-aligned Scope 3
emissions reduction targets
✔ We continued to publish detailed information on ESG initiatives and efforts, and published another annual Impact Report in April 2023
Board and
Corporate
Governance
• Stockholders generally understood the board of directors’ position on maintaining its classified structure at this time but would like us to continue to assess the feasibility of
transitioning to annual voting for all directors
• Stockholders also noted they would like us to remove the supermajority voting requirement for charter and bylaw amendments
✔ We have continued to assess governance structures in the context of our business strategy, performance, tenure as a public company, and market practices
Our Impact Priorities
Our mission is to create economic opportunities so people have better lives. We seek to do what is right for our common stock,business, stakeholders, and planet. Our ESG key focus areas include the NASDAQ 100 Technology Index,following five priorities where we believe we have the greatest potential to drive positive impact:
graphic
Economic
Opportunity
• Enable talent to have control over when, where, and with whom they work
• Empower talent on Upwork to upskill, effectively market their skills, and build successful freelance careers
• Close the global opportunity gap by supporting those who face a biased playing field, systemic discrimination, and limited career development opportunities
graphic
Workforce
Innovation and
Wellbeing
• Support the health, safety, and wellbeing of our team members
• Build a culture of engagement, belonging, and high performance in Upwork's remote-first environment
• Embed independent talent and flexibility into our working model
graphic
Diversity,
Inclusion, and
Belonging
(DIBs)
• Put dignity, purpose, community, and fairness at the center of every working moment
• Build a diverse and inclusive workforce to strengthen our team and serve as a model for our users
graphic
Environmental Sustainability
• Meet our commitment to carbon neutrality
• Decrease our Scope 1, 2, and 3 emissions
• Enable our users to reduce their footprint through use of our work marketplace
graphic
Business Integrity and Supplier Engagement
• Uphold strong governance practices to ensure team members act ethically
• Hold clients and talent accountable to one another
• Work with suppliers that meet the needs of our business, support our supplier diversity goals, and align with our mission
For more information on our ESG programs and the NASDAQ Composite Index, respectively. Such returns are basedperformance, see our 2022 Impact Report, published in April 2023, which is available on historical results and areour ESG Reports Hub on our website at upwork.com/about/our-impact/reports-hub. The information contained in our 2022 Impact Report is not intended to suggest future performance. The NASDAQ Composite Index and the NASDAQ 100 Technology Index assume reinvestment of any dividends.

be incorporated into this Proxy Statement.
4 2023 Proxy Statement graphic

TABLE OF CONTENTS

Executive Compensation Philosophy

Upwork’s Demonstrated Value Creation

Our executive compensation philosophy is to provide a competitive compensation program that attracts and retains talented executives, including our Named Executive Officers, whom we identify in the “Compensation Discussion and Analysis” section below, and to motivate and reward them to meet or exceed our short-term and long-term strategic objectives while simultaneously creating sustainable long-term value for our stockholders. We strive to create an executive compensation program that is competitive, rewards achievement of our strategic objectives, and aligns our executives’ interests with those of our stockholders.
Executive Compensation Overview
Core Elements of 2022 Executive Compensation
Compensation Elements
Key Components
Objective and Alignment to Strategy
Base Salary
• Fixed cash
• Attract and retain top talent through market-competitive salary levels that are commensurate with the executive’s role and responsibility
Annual Bonus
• Variable payout based on performance against pre-established targets
• Incentivize achievement of annual business objectives and reward short-term performance
• Compensation Program Revenue (as defined below) performance metric aligns compensation with strategic growth
Long-Term Equity Incentives
• Time-based restricted stock unit, which we refer to as RSU, awards, which vest over a four-year period
• PSU awards, which are subject to both performance-based and time-based vesting requirements
• Align the interests of executives with stockholders
• Motivate long-term sustainable value creation
• Promote retention of top talent
• Incentivize achievement of annual business objectives and reward long-term performance
• Compensation Program Revenue performance metric aligns compensation with strategic growth
graphic2023 Proxy Statement 5

TABLE OF CONTENTS

Corporate Governance Practices

We are committed to effective corporate governance that promotes the long-term interests of our stockholders and strengthens the accountability of our board of directors and management. As we continue to mature as a public company, we are committed to evolving our corporate governance practices in line with our growth. Our board of directors takes a thoughtful approach to our governance structure, regularly assessing a range of factors, including regular stockholder input and feedback. Our board of directors carefully considers each of our corporate governance practices to ensure they are aligned with our state of maturity as a company and the best interests of our stockholders. Key elements include the following:

Board Diversity

We strive to maintain a diverse board of directors and ensure diversity is a factor when identifying potential new directors; four of our eight directors are women, and three directors are fromself-identify as a member of an underrepresented communitiesminority or the LGBTQ+ community3

Independent Board Oversight

Seven of our eight directors are independent, including our chairperson

Board Oversight of ESG

Our nominating and governance committee oversees our corporate responsibility and sustainability programs, including environmental, social, and governance matters, which we refer to as ESG

Proxy Access

We provide a method for stockholders to place their nominees for director on our proxy ballot

Majority Voting for Directors
We have adopted majority voting in uncontested elections of directors
Stock Ownership Guidelines

Our executiveExecutive and board of directorBoard Stock Ownership Guidelines, which we refer to as the Stock Ownership Guidelines, establish stock ownership requirements, including 5x base salary for our Chief Executive Officer

Annual Board Evaluation

Our board of directors and the committees of our board of directors conduct self-evaluations at least annually to assess performance

Majority Voting

In response to stockholder feedback, we have implemented majority voting in uncontested director elections, which will take effect beginning with

Board Oversight of ESG
Our nominating and governance committee oversees our 2022 annual stockholder meeting

corporate responsibility and sustainability programs, including ESG

Clawback Policy

We have adopted a clawback policy for our executive officers that provides for recoupment of incentive-based compensation in the event we adjust or restate our financial statements

and intend to amend the policy as necessary to comply with forthcoming Nasdaq requirements

Board Composition

Our board of directors conducts an annual self-evaluation process, which is used, in part, to assess the current composition of the board of directors and its committees relative to the evolving needs of the business. This exercise is conducted with the goal of ensuring we have developed and maintain a diverse, experienced, and highly qualified board of directors that is representative of our key stakeholders and well positioned to oversee corporate strategy and culture. As part of the evaluation and refreshment process, our board of directors has added threetwo new independent directors since our IPOinitial public offering in 2018: Ms. Brown, Leela Srinivasan and Anilu Vazquez-Ubarri.Vazquez-Ubarri, in addition to Ms. Brown, who joined our board of directors when she became our President and Chief Executive Officer.
3
As defined in The Nasdaq Stock Market LLC, which we refer to as Nasdaq, listing standards.
6 2023 Proxy Statement graphic

TABLE OF CONTENTS

The charts below provide information regarding the tenure and age distribution of our board of directors (as of March 31, 2023).
graphic

We are committed to creating a diverse and inclusive culture, which starts at the top with our board of directors. Four of our eight directors are women, two directors self-identify as being racially or ethnically diverse, and one director self-identifies as LGBTQ+, all. All of whomour directors bring unique experiences and backgroundbackgrounds to Upwork.

The charts above provide information regarding the tenure

Key Expertise, Experience, and age distribution of our board of directors (as of March 31, 2021). We define tenure as including service on the board of directors of Elance, Inc., which we refer to as Elance, or oDesk Corporation, which we refer to as oDesk, prior to the combination of the two companies in March 2014.

Attributes

3 As defined under California law AB 979.

graphic

Key Expertise, Experience, and Attributes

Technology and Product Development

7/8 Directors

Corporate Governance

8/8Directors

Operations

7/8Directors

CEO and Management Experience



8/8Directors

Finance

6/8Directors

graphic

Risk Management

Corporate
Sustainability
and ESG

5/8Directors
graphic
Cybersecurity

4/8Directors

graphic

Compensation / Talent

Finance

7/8Directors
graphic
Human Capital Management



8/8Directors

graphic
International Business

8/8 Directors
graphic
Marketing and Product

5/


6/8Directors

Strategic Planning

graphic
Operations

8/8Directors

graphic

Other Public Company Board Experience



6/8 Directors
graphic
Risk Management

5/8Directors

International

graphic
Strategic Planning

8/8Directors

graphic
Technology and Product Development

8/8 Directors

Stockholder Engagement

Our board of directors and executive management team values feedback from our stockholders. This feedback is a key input in deliberations on our strategy, governance, executive compensation, and other board-level decisions. In addition to our normal-course investor relations activities, we initiated in the past year a dedicated stockholder outreach program to engage with our largest investors on topics including corporate governance, executive compensation, and corporate responsibility and sustainability. From the beginning of 2021 to date, we have contacted stockholders representing approximately 35% of our current shares outstanding and engaged in discussions with approximately 21% of our current shares outstanding. Key themes from our engagement conversations with stockholders include:

graphic2023 Proxy Statement 7

Primary ThemesKey Discussion Points and Stockholder Feedback
CEO Performance Award Granted in 2021

We discussed the performance award the compensation committee granted Ms. Brown in January 2021, comprised of stock options with both service- and performance-based vesting requirements, which we refer to as the CEO Performance Award, and our board of directors’ goals for the award in the context of Upwork’s strategy and executive compensation program.

Stockholders generally noted that they review such awards closely and highlighted the importance of clear disclosure. An overview of the CEO Performance Award can be found under the heading “CEO Performance Award for Ms. Brown” below.

Stockholders also expressed support for the structure and timing of the CEO Performance Award, noting Upwork’s strong 2020 performance, the rigorous performance targets, and the highly competitive landscape for talented chief executive officers.

Long-Term Incentive Compensation

We discussed the introduction of performance stock units, which we refer to as PSUs, into our long-term incentive compensation program, which was well received by stockholders. Stockholders encouraged us to provide relevant disclosure in future proxy statements.

An overview of the PSUs can be found under the heading “2021 PSU Awards” below. We will include additional details regarding our 2021 pay program, including the PSUs, in the proxy statement for our 2022 annual meeting of stockholders.

ESG and Sustainability

We discussed our ESG-related initiatives and disclosures, including our 2020 Annual Impact Report and Emissions Report (which are available at investors.upwork.com), as well as our people strategy and diversity, inclusion, and belonging initiatives.

Stockholders broadly supported these efforts and noted our significant progress to date, particularly as a newly public company.

Stockholders noted their support for our current use of the Sustainability Accounting Standards Board (SASB) framework, and some also flagged the Task Force on Climate-related Financial Disclosures (TCFD) framework, which we are considering adopting in the future, as potentially valuable additional disclosure.

Stockholders affirmed their support of Upwork’s diversity, belonging, and inclusion, which we refer to as DIB, efforts, including our disclosure of EEO-1 data.

graphic
Notice of Annual Meeting of Stockholders

Friday, June 9, 2023

8:00 a.m. Pacific Time
Online at www.virtualshareholdermeeting.com/UPWK2023.
There is no physical location for the Annual Meeting.
Items of Business
Director Outside Board Commitments

Some stockholders highlighted their policies on “overboarding,” and we discussed our board of directors’ approach to director evaluations and the capacity of individual directors.

One of our directors had previously planned, and recently announced that they will reduce the number of boards on which they serve, after which they will be in compliance with the policies of the stockholders who engaged with us on the topic.

Corporate Governance

We discussed Upwork’s evolving governance practices given our existence as a newly public company.

Stockholders noted their support for our adoption of a majority voting standard in uncontested director elections and proxy access right.

Stockholders also encouraged our board of directors to continue its practice of reviewing our governance structures as the business evolves over time.

Corporate Responsibility and Sustainability Highlights

Our mission is to create economic opportunities so people have better lives. In line with our recognition that ESG oversight is critical to our ability to implement meaningful long-term ESG strategies, in 2019 our nominating and governance committee began overseeing the review and assessment with management of our performance, risk, controls, and procedures relating to corporate responsibility and sustainability, including ESG matters. Further, Upwork has an ESG task force composed of personnel from various departments that is responsible for developing and implementing ESG programs and disclosures.

During the past year, we undertook an ESG materiality assessment to help identify ESG-related topics and issues that are most meaningful to our business and stakeholders. This assessment was informed by interviews with both internal and external stakeholders, including employees, executives, stockholders, and freelancers and clients on our work marketplace. With their input, we were able to identify and evaluate the areas they view as material to them as stakeholders and to our business success.

More details on our ESG materiality assessment are included in our 2020 Annual Impact Report, published in April 2021, which is available on the “Investor Relations” section of our website located at investors.upwork.com. This year’s Annual Impact Report also includes additional disclosures, including enhanced quantitative disclosures on our workforce diversity. We are committed to continued engagement with our stakeholders going forward and ensuring our practices and disclosures align with evolving ESG-related priorities.

Key Highlights and Achievements from 2020 Include:

Diversity, Inclusion,
and Belonging (DIB)

Environmental
Sustainability

The Upwork
Foundation Initiative

●  Evolved and strengthened DIB infrastructure, such as actively engaging with our employee resource groups, in order to foster a sense of workplace belonging

●  Achieved carbon neutrality and publicly committed to maintaining carbon neutrality moving forward

●  Established in 2018 to further our mission—to create economic opportunities so people have better lives—by serving groups at risk of being left behind by the Fourth Industrial Revolution

●  Committed $200,000 to organizations that support racial justice and the Black community

●  Reduced our carbon footprint through adoption of remote-first work model

●  Funds high-performing nonprofits that cultivate inclusive learning and economic opportunities

●  Surveyed team members to gather feedback and monitor our culture, receiving high response rates and employee satisfaction scores

●  Published an Emissions Report

●  Supported Upwork’s award of $1 million in talent grants to 40 organizations working to mitigate the COVID-19 pandemic’s devastating impact

For more information on our ESG-related efforts, see the “Corporate Responsibility and Sustainability” section below in this Proxy Statement, as well as our 2020 Annual Impact Report, which is available on the “Investor Relations” section of our website located at investors.upwork.com.

Executive Compensation Philosophy

Our executive compensation philosophy is to provide a competitive compensation program that attracts and retains talented executives, including our Named Executive Officers, whom we identify in the “Compensation Discussion and Analysis” section below, and to motivate and reward them to meet or exceed our short-term and long-term strategic objectives while simultaneously creating sustainable long-term value for our stockholders.

Executive Compensation Overview

Key Components of 2020 Executive Compensation

Compensation ElementsKey ComponentsObjective and Alignment to Strategy
Base Salary●  Fixed cash●  Attract and retain top talent through market-competitive levels
Annual Bonus

●  Variable payout based on performance against pre-established targets

●  Incentivize achievement of annual business objectives and reward short-term performance

●  Revenue performance metric aligns compensation with strategic growth

Long-Term Equity Incentives

●  Time-based restricted stock unit awards, which we refer to as RSUs, vest over four-year period

●  Align the interests of executives with stockholders

●  Motivate long-term sustainable value creation

●  Promote retention of top talent

UPWORK INC.

475 Brannan Street, Suite 430

San Francisco, California 94107

NOTICE OF ANNUAL MEETING OF STOCKHOLDERS

Time and Date:Tuesday, June 1, 2021, at 8:00 a.m. Pacific Time
Place:The meeting can be accessed by visiting www.virtualshareholdermeeting.com/UPWK2021, where you will be able to listen to the meeting live, submit questions, and vote online.
Items of Business:1.
Elect the threetwo Class IIIII directors named in the accompanying proxy statement,Proxy Statement, each to serve a three-year term expiring at the 20242026 annual meeting of stockholders and until such director’s successor is elected and qualified.qualified, or until such director’s earlier death, resignation, disqualification, or removal.
2.
Ratify the appointment of PricewaterhouseCoopers LLP as our independent registered public accounting firm for the year ending December 31, 2021.2023.
3.
Approve, on a non-binding advisory basis, the compensation paid by us to our Named Executive Officers as disclosed in this Proxy Statement.
4.
Approve a restated certificate of incorporation, which we refer to as the Restated Certificate of Incorporation, in order to reflect recently adopted Delaware law provisions regarding officer exculpation and to make certain other technical and administrative changes, each as reflected in the Restated Certificate of Incorporation and described in the Proxy Statement.
4.5.
Transact such other business as may properly come before the Annual Meeting or any adjournment or postponement thereof.
Record Date
April 10, 2023, which we refer to as the Record Date.
Only stockholders of record at the close of business on the Record Date are entitled to receive notice of, and to vote at, the Annual Meeting and any adjournments thereof.
Participation in Annual Meeting
We are pleased to invite you to participate in our Annual Meeting, which will be conducted exclusively online at www.virtualshareholdermeeting.com/UPWK2023. Please see “Important Information About the Annual Meeting” for additional information.
The Annual Meeting will begin promptly at 8:00 a.m. Pacific Time. The virtual meeting room will open at 7:45 a.m. Pacific Time for registration.
Voting
Your vote is very important to us. Please act as soon as possible to vote your shares, even if you plan to participate in the Annual Meeting. For specific instructions on how to vote your shares, please see “Frequently Asked Questions–Voting Information” beginning on page 90 of this Proxy Statement.
graphic
Record Date:
Internet
Visit the website on your proxy card
Only stockholders of record at
graphic
By Telephone
1-800-690-6903
graphic
By Mail
Mark, sign, date, and return your proxy card in the close of business on April 5, 2021 are entitled to notice of, and to vote at, the meeting and any adjournments thereof.
Voting:Each share of common stock that you own represents one vote. For questions regarding your stock ownership, you may contact us through our website at investors.upwork.com or, if you are a registered holder, our transfer agent, Computershare Trust Company, N.A., through its website at www-us.computershare.com or by phone at (800) 736-3001.enclosed envelope

This notice of the Annual Meeting, proxy statement,Proxy Statement, and form of proxy are being distributed and made available on or about April 20, 2021.

28, 2023.

Whether or not you plan to attend the virtual Annual Meeting, we encourage you to vote and submit your proxy through the internet or by telephone or to request and submit your proxy card as soon as possible, so that your shares may be represented at the meeting.

By Order of the Board of Directors,
graphic
Brian Levey

Corporate Secretary

San Francisco, California

April 20, 2021
28, 2023
8 2023 Proxy Statement graphic

UPWORK INC.
475 Brannan Street, Suite 430
San Francisco, California 94107

PROXY STATEMENT FOR THE 2021 ANNUAL MEETINGTABLE OF STOCKHOLDERSCONTENTS

INFORMATION ABOUT SOLICITATION AND VOTING

The accompanying proxy is solicited by our board of directors on behalf of Upwork Inc. for use at our 2021 Annual Meeting of Stockholders, which we refer to asImportant Information About the Annual Meeting to be held virtually at www.virtualshareholdermeeting.com/UPWK2021 on Tuesday, June 1, 2021, at 8:00 a.m. Pacific Time, and any adjournment or postponement thereof. The Notice of Internet Availability of Proxy Materials and this proxy statement for the Annual Meeting, which we refer to as this Proxy Statement, and the accompanying form of proxy were first distributed and made available on the internet to stockholders on or about April 20, 2021. This Proxy Statement includes information that we are required to provide to you pursuant to the rules and regulations of the U.S. Securities and Exchange Commission, which we refer to as the SEC, and is designed to assist you in voting your shares. In this Proxy Statement, we refer to Upwork Inc. as “Upwork,” “we,” or “us.”

INTERNET AVAILABILITY OF PROXY MATERIALS

In accordance with SEC rules, we are using the internet as our primary means of furnishing proxy materials to stockholders. Consequently, most stockholders will not receive paper copies of our proxy materials. We will instead send these stockholders a Notice of Internet Availability of Proxy Materials with instructions for accessing the proxy materials, including our Proxy Statement and annual report to stockholders, and voting via the internet. The Notice of Internet Availability of Proxy Materials also provides information on how stockholders may obtain paper copies of our proxy materials if they so choose. We believe this means of delivery makes the proxy distribution process more efficient and less costly and helps in conserving natural resources.

GENERAL INFORMATION ABOUT THE MEETING

Record Date; Quorum

Only holders of record of our common stock at the close of business on April 5, 2021, which we refer to as the Record Date, will be entitled to vote at the Annual Meeting. At the close of business on the Record Date, there were 125,962,107 shares of our common stock outstanding and entitled to vote. For 10 days prior to the Annual Meeting, a complete list of the stockholders entitled to vote at the

Our Annual Meeting will be available for examinationconducted online only, via live webcast. Stockholders will be able to access the meeting live by any stockholder for any purpose relatingvisiting www.virtualshareholdermeeting.com/UPWK2023.
We have conducted efficient and effective virtual meetings since 2019. We intend to continue to ensure that our stockholders are afforded the Annual Meeting during ordinary business hourssame rights and opportunities to participate virtually as they would at our headquarters. A list of stockholders entitled to vote at the Annual Meeting will also be available for examination on the internet throughan in-person meeting. We believe the virtual web conference during the Annual Meeting.

The holders of a majority of the voting power of the shares of our common stock issuedformat makes it easier for stockholders to attend and outstandingparticipate fully and entitled to vote at the Annual Meeting as of the Record Date must be present at the Annual Meetingequally in order to hold the Annual Meeting and conduct business. This presence is called a quorum. Your shares are counted as present at the Annual Meeting if you are present and vote at the Annual Meeting or if you have properly submitted a proxy.

Voting Rights; Required Vote

In deciding all matters at the Annual Meeting, as of the close of business on the Record Date, each share of common stock represents one vote. We do not have cumulative voting rights for the election of directors. You may vote all shares owned by you as of the Record Date, including (i) shares held directly in your name as the stockholder of record and (ii) shares held for you as the beneficial owner in street name through a broker, bank, trustee, or other nominee.

10 

Stockholder of Record: Shares Registered in Your Name. If, on the Record Date, your shares were registered directly in your name with our transfer agent, Computershare Trust Company, N.A., then you are considered the stockholder of record with respect to those shares. As a stockholder of record, you may vote at the Annual Meeting or vote by telephone, through the internet, or if you request or receive paper proxy materials, by filling out and returning the proxy card.

Beneficial Owner: Shares Registered in the Name of a Broker or Nominee. If, on the Record Date, your shares were held in an account with a broker, bank, trustee, or other nominee on your behalf, then you are considered the beneficial owner of shares held in “street name.” As the beneficial owner, you have the right to direct your nominee on how to vote your shares by following the voting instructions you receive. Your nominee has only limited authority to vote your shares without your instructions, as described below.

If you were a beneficial owner at the close of business on the Record Date, you may attend the Annual Meeting. You will need the 16-digit Control Number found on your NoticeOur virtual meeting format helps us engage with all stockholders regardless of Internet Availability of Proxy Materials, your proxy card,size, resources, or the instructions that accompany your proxy materials if you wish to attend the Annual Meeting with the right to votephysical location, saves us and submit a question. Even if you do not have your 16-digit Control Number or were not a stockholder as of the close of business on the Record Date, you can still access the meeting, but will not be able to vote at the meeting or submit a question.

If your shares are held in street name, follow the voting instructions you receive from your nominee.

Each director will be elected by a plurality of the votes cast, which means that the three nominees receiving the highest number of “FOR” votes will be elected. You may vote “FOR ALL NOMINEES,” “WITHHOLD AUTHORITY FOR ALL NOMINEES,” or “FOR ALL EXCEPT” one or more of the nominees you specify. Ratification of the appointment of PricewaterhouseCoopers LLP asstockholders time and money, and reduces our independent registered public accounting firm for the year ending December 31, 2021, will be obtained if the number of votes cast “FOR” the proposal at the Annual Meeting exceeds the number of votes cast “AGAINST” the proposal. Approval, on a non-binding advisory basis, of the compensation paid by us to our Named Executive Officers (as defined herein) as disclosed in this Proxy Statement will be obtained if the number of votes cast “FOR” the proposal at the Annual Meeting exceeds the number of votes cast “AGAINST” the proposal. Abstentions (shares present at the Annual Meeting and marked “abstain”) are counted for purposes of determining whether a quorum is present and have no effect on the outcome of the matters voted upon.

Broker non-votes occur when shares held by a broker for a beneficial owner are not voted because the broker did not receive voting instructions from the beneficial owner and lacked discretionary authority to vote the shares. A broker is entitled to vote shares held for a beneficial owner on “routine” matters without instructions from the beneficial owner of those shares. Absent instructions from the beneficial owner of such shares, a broker is not entitled to vote shares held for a beneficial owner on “non-routine” matters. At our Annual Meeting, only the ratification of PricewaterhouseCoopers LLP as our independent registered public accounting firm for the year ending December 31, 2021, is considered a routine matter. The proposal for the election of directors and any other proposals presented at the Annual Meeting are non-routine matters. Broker non-votes are counted for purposes of determining whether a quorum is present and have no effect on the outcome of the matters voted upon. Accordingly, we encourage you to provide voting instructions to your broker, whether or not you plan to attend the Annual Meeting.

11 
environmental impact.

Recommendations of Our Board of Directors on Each of the Proposals Scheduled to Be Voted on at the Annual Meeting

Our board of directors recommends that you vote “FOR ALL NOMINEES” in the election of the Class III directors named in this Proxy Statement, which we refer to as Proposal No. 1, “FOR” the ratification of the appointment of PricewaterhouseCoopers LLP as our independent registered public accounting firm for the year ending December 31, 2021, which we refer to as Proposal No. 2, and “FOR” the approval, on a non-binding advisory basis, of the compensation of our Named Executive Officers as disclosed in this Proxy Statement, which we refer to as Proposal No. 3. None of our directors or Named Executive Officers have any substantial interest in any matter to be acted upon, other than, with respect to our Named Executive Officers, Proposal No. 3 and, with respect to Hayden Brown, Gregory C. Gretsch, and Anilu Vazquez-Ubarri, Proposal No. 1.

Voting Instructions; Voting of Proxies

If you are a stockholder of record, you may:

vote via the virtual meeting website—any stockholder can attend the Annual Meeting by visiting www.virtualshareholdermeeting.com/UPWK2021, where stockholders may vote and submit questions during the meeting. The meeting starts at 8:00 a.m. Pacific Time. Please have your 16-digit Control Number to join the Annual Meeting. Instructions on how to attend and participate via the internet are posted at www.proxyvote.com;

vote by telephone or through the internet—in order to do so, please follow the instructions shown on the Notice of Internet Availability of Proxy Materials or your proxy card; or
vote by mail—if you request or receive a paper proxy card and voting instructions by mail, simply complete, sign, and date the enclosed proxy card and promptly return it in the envelope provided or, if the envelope is missing, please mail your completed proxy card to Vote Processing, c/o Broadridge Financial Solutions, Inc., 51 Mercedes Way, Edgewood, New York 11717. Your signed and dated proxy card must be received prior to the Annual Meeting in order to be voted.

Votes submitted by telephone or through the internet must be received by 11:59 p.m. Eastern Time on May 31, 2021. Submitting your proxy, whether by telephone, through the internet, or if you request or receive a paper proxy card, by mail, will not affect your right to vote should you decide to attend the Annual Meeting. If you are not the stockholder of record, please refer to the voting instructions provided by your nominee to direct your nominee on how to vote your shares. Your vote is important. Whether or not you plan to attend the Annual Meeting, we urge you to vote by proxy to ensure that your vote is counted.

All proxies will be voted in accordance with the instructions specified. If you sign a physical proxy card and return it without instructions as to how your shares should be voted on a particular proposal at the Annual Meeting, your shares will be voted in accordance with the recommendations of our board of directors stated above.

If you do not vote and you hold your shares in street name, and your broker does not have discretionary power to vote your shares, your shares may constitute “broker non-votes” (as described above) and will not be counted in determining the number of shares necessary for approval of the proposals. However, shares that constitute broker non-votes will be counted for the purpose of establishing a quorum for the Annual Meeting.

If you receive more than one proxy card, your shares are registered in more than one name or are registered in different accounts. To make certain all of your shares are voted, please follow the instructions included on each proxy card and vote each proxy card by telephone, through the internet, or by mail. If you requested or received paper proxy materials and you intend to vote by mail, please complete, sign, and return each proxy card you received to ensure that all of your shares are voted.

12 

Expenses of Soliciting Proxies

We have retained D.F. King & Co., Inc. to assist us with the solicitation of proxies, for which we will pay an aggregate fee of $15,000, plus reasonable and documented costs and expenses. We will pay the expenses of soliciting proxies, including preparation, assembly, printing, and mailing of this Proxy Statement, the proxy card, and any other information furnished to stockholders. Following the original mailing of the soliciting materials, we and our agents, including directors, officers, and other employees, without additional compensation, may solicit proxies by mail, email, telephone, facsimile, or other similar means, or in person. Following the original mailing of the soliciting materials, we will request brokers, custodians, nominees, and other record holders to forward copies of the soliciting materials to persons for whom they hold shares and to request authority for the exercise of proxies. In such cases, we, upon the request of the record holders, will reimburse such holders for their reasonable expenses. If you choose to access the proxy materials or vote through the internet, you are responsible for any internet access charges you may incur.

Revocability of Proxies

A stockholder of record who has given a proxy may revoke it at any time before it is exercised at the Annual Meeting by:

delivering to our Corporate Secretary by mail a written notice stating that the proxy is revoked;
signing and delivering a proxy bearing a later date;
voting again by telephone or through the internet; or
attending and voting at the Annual Meeting (although attendance at the Annual Meeting will not, by itself, revoke a proxy).

Please note, however, that if your shares are held of record by a broker, bank, or other nominee and you wish to revoke a proxy, you must contact that firm to revoke any prior voting instructions.

Voting Results

Voting results will be tabulated and certified by the inspector of elections appointed for the Annual Meeting. The preliminary voting results will be announced at the Annual Meeting. The final results will be tallied by the inspector of elections and filed with the SEC in a current report on Form 8-K within four business days of the Annual Meeting.

Participating in the Annual Meeting

To participate

Instructions on how to attend the Annual Meeting are posted at www.virtualshareholdermeeting.com/UPWK2023.
You may log in to the virtual meeting visit www.virtualshareholdermeeting.com/UPWK2021 and enterplatform beginning at 7:45 a.m. Pacific Time on June 9, 2023. The meeting will begin promptly at 8:00 a.m. Pacific Time.
You will need the 16-digit Control Number included oncontrol number provided in your proxy card or onmaterials to attend the instructions that accompanied your proxy materials.

If you wish to submit a questionAnnual Meeting at www.virtualshareholdermeeting.com/UPWK2023.

Stockholders of record and beneficial owners as of the Record Date may vote their shares electronically during the Annual Meeting, log into the virtual meeting platform at www.virtualshareholdermeeting.com/UPWK2021, type your question into the “Ask a Question” field, and click “Submit.” If your question is properly submitted during the relevant portion of the meeting agenda, we will respond to your question during the live webcast, subject to time constraints. Questions that are substantially similar may be grouped and answered together to avoid repetition. We reserve the right to exclude questions that are irrelevant to meeting matters, irrelevant to the business of Upwork, or derogatory or in bad taste; that relate to pending or threatened litigation; that are personal grievances; or that are otherwise inappropriate (as determined by the chair of the Annual Meeting). A webcast replay of the Annual Meeting, including the Q&A session, will be archived on the “Investor Relations” section of our website, which is located at investors.upwork.com.

If we experience technical difficulties during the meeting (e.g., a temporary or prolonged power outage), we will determine whether the meeting can be promptly reconvened (if the technical difficulty is temporary) or whether the meeting will need to be reconvened on a later day (if the technical difficulty is more prolonged). In any situation, we will promptly notify stockholders of the decision via www.virtualshareholdermeeting.com/UPWK2021.Meeting.

If you encounter technicalany difficulties accessing our meeting or asking questions during the meeting,Annual Meeting, a support line will be available on the login page of the virtual meeting website.

Additional Information About the Annual Meeting
Stockholders may submit questions during the live meeting at www.virtualshareholdermeeting.com/UPWK2023.
During the meeting’s live Q&A session, we will answer questions as time permits.
Our rules of conduct and procedure for the meeting generally provide that we limit each stockholder to one question so that we can answer questions from as many stockholders as possible. Questions should be succinct and cover only one topic per question. Questions from multiple stockholders on the same topic or that are otherwise related may be grouped and answered together. In addition, questions may be edited for brevity and grammatical corrections.
We do not intend to address any questions that are, among other things: irrelevant to our business or to the business of the Annual Meeting; related to nonpublic information about our company; related to personal matters or grievances; derogatory or otherwise not in good taste; in substance, repetitious or already made by other persons; in furtherance of the stockholder’s personal or business interests; related to pending or threatened litigation; or out of order or not otherwise suitable for the conduct of the Annual Meeting as determined by the chairperson of the Annual Meeting or our Corporate Secretary in their sole judgment.
If there are matters of individual concern to a stockholder (rather than of general concern to all stockholders), or if we are not able to answer all the questions posed, stockholders may contact us separately after the meeting through our Investor Relations department by email at investor@upwork.com.
A webcast replay of the Annual Meeting, including the Q&A session, will be available for 90 days following the Annual Meeting in the “Investor Relations” section of our website, which is located at investors.upwork.com.
13 
graphic2023 Proxy Statement 9


BOARD

TABLE OF DIRECTORS AND COMMITTEES OF THE BOARD OF DIRECTORS;CONTENTS

CORPORATE GOVERNANCE STANDARDS AND DIRECTOR INDEPENDENCE

Board of Directors and Committees of the Board of Directors; Corporate Governance Standards and Director Independence
We are strongly committed to good corporate governance practices. These practices provide an important framework within which our board of directors and management can pursue our strategic objectives for the benefit of our stockholders.

Corporate and Compensation Governance Highlights
Corporate and Compensation Governance Highlights
Board Diversity
We strive to maintain a diverse board of directors and ensure diversity is a factor taken into account when identifying potential new directors. Four of our eight directors are women, and three directors are fromself-identify as a member of an underrepresented communities.minority or the LGBTQ+ community64
Independence
Independent Board Oversight
Seven of our eight directors are “independent” as defined by The Nasdaq Stock Market LLC,and the Securities and Exchange Commission, which we refer to as Nasdaq, and the SEC, and we have an independent director serving as our chairperson.chairperson
Proxy Access
Our amended and restated bylaws provide a method for stockholders to place their nominees for director on our proxy ballot.ballot
Majority Voting for Directors
Beginning with our 2022 annual meeting of stockholders, we are implementing
We have adopted majority voting in uncontested elections of directors.directors
Stock Ownership Guidelines
Our Executive and Board Stock Ownership Guidelines, which we refer to as the Stock Ownership Guidelines establish the level of stock ownership and holding requirements expected of our directors and executive officers.officers, including 5x base salary for our Chief Executive Officer
Annual Board Evaluation
Our board of directors and the committees of our board of directors conduct self-evaluations at least annually to assess performance.performance
Annual Compensation Evaluation
With the help of an independent compensation consultant, our compensation committee conducts annual reviews of the compensation of all our executive officers.officers
Corporate Responsibility
Our nominating and governance committee is responsible for reviewing and assessing our performance and procedures relating to corporate responsibility and sustainability, including ESG matters.matters
ESG Task ForceManagement
Our ESG Program Office, which comprises our ESG Senior Program Manager and other members of our legal department and is focused on engaging key stakeholders and strengthening our ESG performance, is responsible for reporting to the nominating and governance committee overseesat least biannually. Our ESG Program Office is supported by our ESG task force,Task Force, which comprises personnelis a management-level committee of senior leaders and subject matter experts from various departments and is responsible for developing and implementing ESG programs.programs
Compensation Risk Oversight
Our compensation committee, on at least an annual basis, evaluates our compensation programs to ensure that they do not encourage our employees, including our executive officers, to take inappropriate or excessive risk.risk
Clawback Policy
We have adopted a clawback policy for our executive officers that provides for recoupment of incentive-based compensation in the event we adjust or restate our financial statements.statements and intend to amend the policy as necessary to comply with forthcoming Nasdaq requirements

6
4
As defined under California law AB 979.in the Nasdaq listing standards.
14 
10 2023 Proxy Statement graphic

TABLE OF CONTENTS

Corporate Governance Guidelines

Our board of directors has adopted Corporate Governance Guidelines that set forth expectations for directors, director independence standards, board committee structure and functions, and other policies for the governance of our company. Our Corporate Governance Guidelines are available onin the “Investor Relations” section of our website, which is located at investors.upwork.com, by clicking “Documents & Charters” in the “Governance” section of our website. Our nominating and governance committee reviews the Corporate Governance Guidelines annually, and changes are recommended to our board of directors as warranted.

Board Leadership Structure

Our Corporate Governance Guidelines provide that our board of directors shall be free to choose its chairperson in any way that it considers in the best interests of our company, and that the nominating and governance committee periodically considers the leadership structure of our board of directors and makes such recommendations to our board of directors with respect thereto as appropriate.

Our board of directors believes it is important to have flexibility in selecting the chairperson of the board of directors and our board leadership structure. Any changes to the leadership structure of our board of directors, if made, will be promptly disclosed in the “Investor Relations” section of our website and will be reflected in our proxy materials for the next annual meeting of stockholders. In making leadership structure determinations, the board of directors considers many factors, including the specific needs of the business and what is in the best interests of our stockholders. Our board of directors, in its sole discretion, may seek input from our stockholders on the leadership structure of the board of directors.

Currently, the positions of chairperson and chief executive officer are held by different individuals. Thomas Layton is the chairperson of our board of directors. Mr. Layton has served as a member of our board of directors and chairperson since our inception. Our board of directors believes that Mr. Layton’s historical knowledge, operational expertise, and extensive leadership experience, including serving as the chairperson of our board of directors since our inception, make him well qualified to serve as chairperson of our board of directors. Mr. Layton is an independent director and, accordingly, our board of directors has not designated a lead independent director.

Our Corporate Governance Guidelines also provide that, when the positions of chairperson and chief executive officer are held by the same person, the independent directors may designate a “lead independent director.” In cases in which the chairperson and chief executive officer are the same person and a lead independent director has been designated, the chairperson schedules and sets the agenda for meetings of our board of directors in consultation with the lead independent director, and the chairperson, or if the chairperson is not present, the lead independent director, chairs such meetings. The responsibilities of the lead independent director include: calling meetings of the independent directors; presiding at executive sessions of independent directors; serving as aprincipal liaison between the chairperson and the independent directors; disseminating information to the rest of our board of directors; being available under appropriate circumstances for communication with stockholders; providing leadership to the board of directors if circumstances arise in which the role of chief executive officer and chairperson may be, or may be perceived to be, in conflict, and performing such other functions and responsibilities as requested by our board of directors from time to time.

Mr. Layton is an independent director, and accordingly, our board of directors has not designated a lead independent director.

Our Board of Directors’ Role in Risk Oversight

Our board of directors, as a whole, has responsibility for risk oversight, although the committees of our board of directors oversee and review risk areas that are particularly relevant to them. The risk oversight responsibility of our board of directors and its committees is supported by our management reporting processes, which are designed to provide visibility to our board of directors and to our personnel who are responsible for risk assessment and information about the identification, assessment, and management of critical risks and management’s risk-mitigation strategies. These areasOur board of directors and its committees engage, as appropriate, external advisors and experts to assist in anticipating future threats and trends and assessing our risk environment. Areas of focus include, among others, competitive, economic, operational, financial (accounting,
graphic2023 Proxy Statement 11

TABLE OF CONTENTS

(accounting, credit, investment, liquidity, and tax), legal, regulatory, cybersecurity, privacy, compliance, and reputational risks. Our board of directors reviews strategic and operational risk in the context of memorandums distributed prior to, and discussions, question-and-answer sessions, and reports from the management team at, each regular board meeting,meeting; receives reports on all significant committee activities at each regular board meeting,meeting; and evaluates the risks inherent in significant transactions. OurRisk mitigation efforts are then reported by management to the audit risk and compliance committee which we refer to as ouror board of directors throughout the year. Our audit committee assists our board of directors in fulfilling its oversight responsibilities with respect to risk management.

15 

Each committee of our board of directors meets with key management personnel and representatives of outside advisors to oversee risks associated with their respective principal areas of focus.

Audit, Risk and Compliance Committee
Our audit committee reviews
Compensation Committee
Nominating and Governance
Committee
• Reviews our major financial and other risk exposures, our internal control over financial reporting, our disclosure controls and procedures, and our legal and regulatory compliance and, among other things, discusses with management and our independent auditor guidelines and policies with respect to risk assessment and risk management. Our audit committee also reviews
management
• Reviews matters relating to cybersecurity and data privacy and security and reports to our board of directors regarding such matters.
matters
Our compensation committee evaluates
• Evaluates our major compensation-related risk exposures and the steps management has taken to monitor or mitigate such exposures.
exposures
Our nominating and governance committee assesses
• Assesses risks relating to our corporate governance practices, reviews and assesses our performance, risks, controls, and procedures relating to corporate responsibility and sustainability, including ESG, reviews the independence of our board of directors, and reviews and discusses the narrative disclosure regarding our board of directors’ leadership structure and role in risk oversight.oversight

We believe this division of responsibilities is an effective approach for addressing the risks we face and that our board leadership structure supports this approach.
Cybersecurity Risk Oversight
Securing the information of our users, team members, vendors, and other third parties is important to us. We have adopted physical, technological, and administrative controls on data security and have a defined procedure for data incident detection, containment, response, and remediation. While everyone at our company plays a part in managing these risks, oversight responsibility is shared by our board of directors, our audit committee, and management.
Our Chief Information Security Officer provides regular cybersecurity updates in the form of written reports and presentations to our audit committee at quarterly meetings and to the full board of directors annually. Our audit committee regularly reviews metrics about cyber threat response preparedness, program maturity milestones, risk mitigation status, and the current and emerging threat landscape. Additionally, we leverage the National Institute of Standards and Technology security framework to drive strategic direction and maturity improvement and engage third-party security experts for risk assessments and program enhancements. We are ISO certified in Information Security Management Systems, an internationally recognized certification that is independently audited by a third party.
12 2023 Proxy Statement graphic

TABLE OF CONTENTS

Majority Voting Standard for Director Elections and Director Resignation Policy

Commencing with our 2022 annual meeting of stockholders, our

Our amended and restated bylaws provide for a majority voting standard for uncontested elections of directors and require that stockholder director nominations include a written statement as to whether the nominee intends to tender an irrevocable resignation upon such nominee’s election or re-election. The majority voting standard provides that, in uncontested director elections, a director nominee will be elected only if the number of votes cast FOR the nominee exceeds the number of votes cast AGAINST the nominee. In addition, our Corporate Governance Guidelines require each incumbent nominee to submit an irrevocable contingent resignation letter prior to the annual meeting of stockholders in which such election is to take place. This addresses the “holdover” director situation under the Delaware General Corporation Law, which we refer to as the DGCL, pursuant to which a director remains on the board of directors until such director’s successor is elected and qualified. Such resignation becomes effective only upon (i) such nominee’s failure to receive the requisite number of votes for re-election at any future meeting at which such person would face re-election and (ii) our board of directors’ acceptance of such resignation. If the nominee does not receive the requisite number of votes for re-election, our nominating and governance committee will make a recommendation to our board of directors as to whether to accept or reject the resignation, or whether other action should be taken. Our board of directors will act on the nominating and governance committee’s recommendation and publicly disclose its decision and the rationale behind it within 90 days from the date of the certification of the election results.

Independence of Directors

The listing rules of Nasdaq generally require that a majority of the members of a listed company’s board of directors be independent. In addition, the listing rules generally require that, subject to specified exceptions, each member of a listed company’s audit, compensation, and nominating and governance committees be independent.

In addition, audit committee members must also satisfy the independence criteria set forth in Rule 10A-3 under the Securities Exchange Act of 1934, as amended, which we refer to as the Exchange Act. In order to be considered independent for purposes of Rule 10A-3, a member of an audit committee of a listed company may not, other than in his or her capacity as a member of the audit committee, the board of directors, or any other board committee: accept, directly or indirectly, any consulting, advisory, or other compensatory fee from the listed company or any of its subsidiaries; or be an affiliated person of the listed company or any of its subsidiaries.

16 

Our board of directors conducts an annual review of the independence of our directors. In its most recent review, our board of directors determined that Thomas Layton, Gregory C. Gretsch, Kevin Harvey, Elizabeth Nelson, Leela Srinivasan, Gary Steele, and Anilu Vazquez-Ubarri, representing seven of our eight directors, are “independent directors”directors,” as defined under the applicable listing standards of Nasdaq and the applicable rules and regulations promulgated by the SEC. Our board of directors has also determined that all members of our audit committee, compensation committee, and nominating and governance committee are independent and satisfy the relevant SECNasdaq and NasdaqSEC independence requirements for such committees.

graphic2023 Proxy Statement 13

TABLE OF CONTENTS

Committees of Our Board of Directors

Our board of directors has established an audit committee, a compensation committee, and a nominating and governance committee. The composition and responsibilities of each committee are described below. Each of these committees has a written charter approved by our board of directors. Copies of the charters for each committee are available onin the “Investor Relations” section of our website, which is located at investors.upwork.com, by clicking on “Documents & Charters” in the “Governance” section of our website.

Director
Independent
Audit, Risk and
Compliance Committee
Compensation
Committee
Nominating and
Governance Committee
Gregory C. Gretsch graphic
Yes
graphic
graphic
Kevin Harvey
Yes
graphic
Thomas Layton
Yes
graphic
Elizabeth Nelson graphic
Yes
graphic
graphic
Leela Srinivasan
Yes
graphic
Gary Steele
Yes
graphic
Anilu Vazquez-Ubarri
Yes
graphic
graphic  Chair
graphic  Member
graphic  Financial Expert
Audit, Risk and Compliance Committee

Our audit committee is composed of Ms. Nelson, who is the chairperson of the committee, Mr. Gretsch, and Ms. Srinivasan. Each member of our audit committee is independent under the current Nasdaq listing standards and SEC rules and regulations. Each member of our audit committee is financially literate as required by the current Nasdaq listing standards. In addition, our board of directors has determined that Ms. Nelson isand Mr. Gretsch both satisfy the requirements for an “audit committee financial expert” as defined in SEC rules and regulations. This designation does not impose any duties, obligations, or liabilities that are greater than those generally imposed on members of our audit committee and our board of directors. Our audit committee is responsible for, among other things:

selecting a firm to serve as the independent registered public accounting firm to audit our financial statements;
reviewing the independence of the independent registered public accounting firm;
discussing the scope and results of the audit with the independent registered public accounting firm and reviewing, with management and that firm, our interim and year-end operating results;
establishing procedures for employees to anonymously submit concerns about questionable accounting or audit matters;
considering the adequacy of our internal controls, internal audit function, and cybersecurity controls and procedures;
reviewing material related party transactions or those that require disclosure;
reviewing legal, financial, technology, and enterprise risk exposures and the steps management has taken to monitor and control such exposures; and
approving or, as permitted, pre-approving all audit and non-audit services to be performed by the independent registered public accounting firm.

selecting a firm to serve as the independent registered public accounting firm to audit our financial statements;
reviewing the independence of the independent registered public accounting firm;
discussing the scope and results of the audit with the independent registered public accounting firm and reviewing, with management and that firm, our interim and year-end operating results;
establishing procedures for employees to anonymously submit concerns about questionable accounting or audit matters;
considering the adequacy of our internal controls, our internal audit function, and our cybersecurity, data privacy, and other information technology controls and procedures;
reviewing material related party transactions, including those that require disclosure;
reviewing legal, regulatory, financial, technology, payment, and enterprise risk exposures and compliance and the steps management has taken to monitor and control such exposures and compliance; and
approving or, as permitted, pre-approving all audit and non-audit services to be performed by the independent registered public accounting firm.
17 
14 2023 Proxy Statement graphic

TABLE OF CONTENTS

Compensation Committee

Our compensation committee is composed of Mr. Gretsch, who is the chairperson of the committee, Mr. Steele, and Ms. Nelson, and Mr. Steele.Vazquez-Ubarri. The composition of our compensation committee meets the requirements for independence under current Nasdaq listing standards and SEC rules and regulations. Each member of this committee is a non-employee director, as defined in SEC rules and regulations. Our compensation committee is responsible for, among other things:

reviewing and approving, or recommending that our board of directors approve, the compensation of our executive officers;
reviewing succession plans for our Chief Executive Officer;
reviewing and recommending to our board of directors the compensation of our non-employee directors;
administering our stock and equity incentive plans; and
establishing our overall compensation philosophy.

reviewing and approving, or recommending that our board of directors approve, the compensation of our executive officers;
reviewing succession plans for our Chief Executive Officer;
reviewing and recommending to our board of directors the compensation of our non-employee directors;
administering our stock and equity incentive plans; and
establishing our overall compensation philosophy.
Nominating and Governance Committee

Our nominating and governance committee is composed of Mr. Layton, who is the chairperson of the committee, Mr. Harvey, and Ms. Vazquez-Ubarri.Nelson. The composition of our nominating and governance committee meets the requirements for independence under current Nasdaq listing standards. Our nominating and governance committee is responsible for, among other things:

identifying and recommending candidates for membership on our board of directors;

recommending directors to serve on board committees;
reviewing and recommending to our board of directors any changes to our corporate governance principles;
reviewing proposed waivers of the code of conduct for directors and officers;
overseeing the process of evaluating the performance of our board of directors;
advising our board of directors on corporate governance matters; and
developing and overseeing of programs related to corporate responsibility and sustainability, including ESG matters.

identifying and recommending candidates for membership on our board of directors;
recommending directors to serve on board committees;
reviewing and recommending to our board of directors any changes to our corporate governance principles;
reviewing proposed waivers of our Code of Business Conduct and Ethics for directors and officers;
overseeing the process of evaluating the performance of our board of directors;
advising our board of directors on corporate governance matters; and
developing and overseeing programs related to corporate responsibility and sustainability and ESG matters, including reviewing and assessing our performance, risks, controls, and procedures relating to corporate responsibility and sustainability.
Management Succession Planning

Our board of directors recognizes that one of its most important duties is its oversight of succession planning for our Chief Executive Officer. Our board of directors has delegated primary oversight responsibility for succession planning for our Chief Executive Officer to the compensation committee and the chairperson of our board of directors. Our Chief Executive Officer is responsible for identifying, evaluating, and selecting potential successors for our Chief Executive Officer’s direct reports. Our board of directors continues to regularly evaluate its succession planning to ensure that we are well-positionedwell positioned to continue to execute on our corporate strategy.

Oversight of Corporate Strategy

Our board of directors actively oversees management’s establishment and execution of corporate strategy, including major business and organizational initiatives, annual budget and long-term strategic plans, capital allocation priorities, potential corporate development opportunities, and risk management. At its regularly scheduled meetings and throughout the year, our board of directors receives information and formal updates from our management and actively engages with the senior leadership team with respect to our corporate
graphic2023 Proxy Statement 15

TABLE OF CONTENTS

strategy. Our board of directors’ diverse skill set and experience enhances our board of directors’ ability to support management in the execution and evaluation of our corporate strategy. The independent members of our board of directors also hold regularly scheduled executive sessions at which strategy is discussed.

18 

Compensation Committee Interlocks and Insider Participation

The members of our compensation committee during 20202022 were Mr. Gretsch, Ms. Nelson (until April 2022), Mr. Steele, and Mr. Steele.Ms. Vazquez-Ubarri (beginning April 2022). None of the members of our compensation committee in 2020 was2022 were at any time an officer or employee of ours or any of our subsidiaries, and none had or have any relationships with us that are required to be disclosed under Item 404 of Regulation S-K. During 2020,2022, none of our executive officers served as a member of the board of directors, or as a member of the compensation or similar committee, of any entity that has one or more executive officers who served on our board of directors or compensation committee.

Board and Committee Meetings and Attendance

Our board of directors and its committees meet regularly throughout the year, and also hold special meetings and act by written consent from time to time. During 2020,2022, our board of directors met sevensix times and also acted by unanimous written consent. During 2020,2022, each member of our board of directors attended at least 75% of the aggregate of all meetings of our board of directors and of all meetings of committees of our board of directors on which such member served that were held during the period in which such director served. The non-employee directors meet in regularly scheduled executive sessions without management to promote open and honest discussion. During 2020,2022, our audit committee met sixeight times, our compensation committee met foursix times, and our nominating and governance committee met two times.

times, and each committee also acted by unanimous written consent.

Board Attendance at Annual Meeting of Stockholders

Our policy is to invite and encourage each member of our board of directors to be present at our annual meetings of stockholders. All members of our board of directors attended our 20202022 annual meeting of stockholders in their capacity as directors of our company.

Communication with Directors

Stockholders and interested parties who wish to communicate with our board of directors, non-management members of our board of directors as a group, a committee of our board of directors, or a specific member of our board of directors (including our chairperson) may do so by letters addressed to the attention of our Corporate Secretary.

All communications are reviewed by the Corporate Secretary and provided to the members of our board of directors as appropriate. Sales materials, abusive, threatening, or otherwise inappropriate materials, and items unrelated to the duties and responsibilities of our board of directors will not be provided to directors.

The mailing address for these communications is:

Upwork Inc.


c/o Corporate Secretary


655 Montgomery Street, Suite 490, Department 17022


San Francisco, CA 94111-2676

19 
16 2023 Proxy Statement graphic

TABLE OF CONTENTS

Code of Business Conduct and Ethics

We have adopted a Code of Business Conduct and Ethics that applies to all the members of our board of directors, officers, and employees. Our Code of Business Conduct and Ethics is posted onin the “Investor Relations” section of our website, which is located at investors.upwork.com under “Documents & Charters” in the “Governance” section of our website. We intend to satisfy the disclosure requirement under applicable SEC and Nasdaq disclosure requirements regarding amendments to, or waivers of, a provision of our Code of Business Conduct and Ethics by posting such information on our website at the address and location specified above.

Corporate ResponsibilityESG Strategy and Sustainability

Notable Accomplishments

Our mission is to create economic opportunities so people have better lives. We do this by removing friction in the labor market, allowing clients to hire freelanceindependent talent, and helping global independent talent find better opportunities than those available in their local job markets. We believe that operating in a responsible and sustainable way will drive long-term value creation, and we are committed to managing our ESG risks and opportunities.
To help identify ESG-related topics that are most important to our business and stakeholders, we conducted our first ESG materiality assessment in 2020 and will be updating the assessment in 2023. These assessments help us identify, assess, and prioritize sustainability topics that impact Upwork’s enterprise value as well as those that affect society at large. In addition to assessing the perceptions of key stakeholders, including employees, executives, stockholders, talent, and clients, the 2023 assessment will also measure the degree to which ESG topics have or are expected to financially and strategically impact Upwork.
We are committed to continued engagement with our key stakeholders going forward and ensuring our practices and disclosures align with evolving ESG-related priorities.
graphic2023 Proxy Statement 17

TABLE OF CONTENTS

The following table sets forth the key focus areas for our ESG strategy and our notable ESG accomplishments in 2022:
Key Focus Areas for ESG Strategy and Notable ESG Accomplishments in 2022
graphic
Economic Opportunity
• Helping independent talent unlock their potential by connecting professionals
with a range of clients along with resources to support career independence
• Building an inclusive work marketplace by developing programs and features that enable our diverse users to thrive
• Supporting our community through charitable giving programs and partnerships with organizations that align with our impact goals
• Building the future of work by providing thought leadership and resources to independent talent and companies of all sizes
• 2022 notable accomplishments in this area:
 • In response to the war in Ukraine, launched Opportunity Unlimited to help displaced professionals find work and procure the resources they need to prepare for, conduct, and get paid for their work, no matter their location
 • Provided coaching to more than 7,000 independent professionals through Upwork Academy, hosted over 180 events and webinars reaching more than 28,000 people, and launched more than 100 community groups to help talent on Upwork connect and learn from one another
 • Granted $1.68 million through The Upwork Foundation5 to 12 nonprofits serving immigrants, refugees, and asylum seekers
 • Upwork and its employees contributed $183,000 through our matching gifts program to nonprofits supporting diversity, inclusion, and belonging and those addressing humanitarian crises
graphic
Workforce Innovation and Wellbeing
• Growing a hybrid workforce that is defined not only by combining in-person and remote work but also by engaging both employees and independent talent whenever possible
• Implementing leading strategies to support remote organizational effectiveness
• Building out a new workforce research and engagement program that supports dynamic, holistic, and continuous learning
• Offering tools such as Textio U certification in support of an equitable performance review process
• Continuously evaluating our workforce benefits to support the full range of employees’ mental health, wellbeing, and growth
• 2022 notable accomplishments in this area:
 • Built a team to focus on remote organizational effectiveness
 • Increased short-term disability pay for employees to 100% of salary for the first four weeks and modified our time-off policy for domestic payrolled hybrid team members to include 20 paid days off
 • Built out a more robust workforce survey strategy and set new engagement targets for 2023
5
The Upwork Foundation is a philanthropic initiative established in 2018 in connection with our initial public offering. To fund this program for charitable donations, we issued a warrant exercisable for 500,000 shares of our common stock to a donor-advised fund that donates the proceeds from the sale of such shares to non-profit organizations of our choice.
18 2023 Proxy Statement graphic

TABLE OF CONTENTS

Key Focus Areas for ESG Strategy and Notable ESG Accomplishments in 2022
graphic
Diversity, Inclusion, and Belonging (DIBs)
• Dedicating strategic investment in DIBs and integrating DIBs into all of our people programs
• Creating a suite of programs to support women and people of color, including GlowUp and Our Place
• Fostering a sense of workplace belonging through Upwork Belonging Communities
• 2022 notable accomplishments in this area:
 • Launched McKinsey’s Leadership Essentials, a program designed for individual contributors to sharpen core business acumen and self-leadership tools in preparation for leading teams and larger projects/initiatives
 • Evolved our GlowUp program to be an always-on community for Upwork’s leaders of color, enabling them to foster camaraderie and explore shared leadership experiences, opportunities, and challenges throughout the year
• Continued supporting Our Place, an immersive membership community for Upwork’s most senior Black women employees, UPstanders, a program offering workshops to build inclusive practices and advance a collaborative culture at Upwork, and the McKinsey Management Accelerator, a 16-week program for early- to mid-career Black, Asian, and/or Latinx leaders
graphic
Environmental Sustainability
• Reducing our environmental footprint, including our Scope 1, 2, and 3 emissions
• Enabling our users to reduce work-related commutes through the use of our work marketplace
• Committing to transparency of our corporate governance practices around environmental risks and opportunities and methodically assessing, reporting, and verifying our environmental performance data on an annual basis
• Connecting clients and talent focused on sustainability
• 2022 notable accomplishments in this area:
 • Verified our Scope 1, 2, and 3 emissions and maintained carbon-neutral6 operations for the fourth consecutive year
 • Submitted our CDP Climate Change questionnaire, earning a B score
 • Expanded our Scope 3 emissions analysis to include remote work, all supply chain emissions, employee commuting, and business travel
 • Maintained our Global Environmental Policy and E-waste Policy
graphic
Business Integrity and Supplier Engagement
• Following security and privacy best practices to provide a secure, reliable, and compliant work marketplace
• Ensuring ethical business practices and engaging on public policy to maximize opportunity for freelancers and creating a more equitable future of work
• Supporting human rights by enforcing our Global Human Rights Policy and updating our annual Modern Slavery and Human Trafficking Statement
• Working with suppliers that align with our mission and inclusive sourcing goals
• 2022 notable accomplishments in this area:
 • Updated our Privacy Policy and launched a security operations and response product to automate threat investigations and analysis
 • Maintained our SOC 2 Type II, PCI DSS Level 2, and ISO 27001 and 27018 certifications and achieved SOC 3 certification
 • Audited 22 Trust and Safety enforcement areas as part of an ongoing effort to ensure greater consistency and fairness across the platform
 • Maintained our Code of Business Conduct and Ethics, Global Human Rights Policy, Supplier Code of Conduct, and Terms of Service
6
In 2022, our Scope 1 emissions were zero, and our Scope 2 market-based emissions were 15 MTCO2e. We’ve historically offset our operational (Scope 1 and 2) emissions that cannot be avoided, as well as those from our business travel and employee commuting (Scope 3). In 2022, we also offset remote work emissions (Scope 3).
graphic2023 Proxy Statement 19

TABLE OF CONTENTS

For more information on our ESG programs and performance, including our ESG materiality assessment, see our 2022 Impact Report, published in April 2023, which is available on our ESG Reports Hub on our website at upwork.com/about/our-impact/reports-hub. The information contained in our 2022 Impact Report is not intended to be incorporated into this Proxy Statement.
ESG Oversight
Board oversight of our ESG strategy and performance starts with our nominating and governance committee, which oversees our overall ESG performance and provides input on our management of material ESG risks and opportunities, that arise from ESG issues.

We recognize that soundreporting, and progress against ESG oversight is criticaltargets.

Our ESG Program Office, which comprises our ESG Senior Program Manager and other members of the legal department, focuses on engaging key stakeholders and strengthening our ESG performance. Our ESG Program Office briefs the nominating and governance committee at least biannually, which then updates the full board of directors on ESG matters on a biannual basis.
In 2022, we continued to convene members of our abilityESG Task Force, a committee made up of senior leaders and subject matter experts across Upwork, to implement meaningful long-termproactively manage the key ESG strategies. Upwork takestopics identified in our 2020 ESG materiality assessment. Additionally, our ESG Task Force has begun the following approachprocess of assessing matters for our 2023 ESG materiality assessment. Through our ongoing stockholder engagement efforts, we have also engaged with many institutional investors to managingunderstand their ESG riskspriorities and opportunities:

share information about our ESG programs.
ESG Oversight
Board Oversight

Our nominating and governance committee is responsible for reviewing and assessing with management our performance, risks, controls, and procedures relating to corporate responsibility and sustainability, including ESG matters.matters
Functional Leadership
ESG Program Office
Our ESG Program Office, which comprises our ESG Senior Program Manager and other members of the legal department, drives our company-wide strategic approach to ESG and each business function is responsible for identifyingupdates our nominating and deliveringgovernance committee on its own ESG objectives.progress, risks, and ongoing strategy at least biannually
ESG Task Force

Our cross-functional ESG task force is composedTask Force, a committee made up of personnel from various departmentssenior leaders and subject matter experts across Upwork, is responsible for developing and implementing ESG programs and disclosures, and our legal team is responsible for updating our nominating and governance committee periodically throughout the year on progress, risks, and ongoing strategy.

During the past year, we undertook an ESG materiality assessment to help identify ESG-related topics and issues that are most important to our business and stakeholders. This assessment was informed by interviews with both internal and external stakeholders, including employees, executives, stockholders, and freelancers and clients on our work marketplace. With their input we were able to identify and evaluate the topic areas that they view as most important to them as stakeholders and to our business success at Upwork.

More details on our ESG materiality assessment are included in our 2020 Annual Impact Report, published in April 2021, which is available on the “Investor Relations” section of our website located at investors.upwork.com. This year’s Annual Impact Report also includes additional disclosures new since our 2019 Annual Impact Report, including enhanced quantitative disclosures on our workforce diversity. We are committed to continued engagement with these stakeholders going forward and ensuring our practices and disclosures align with evolving ESG-related priorities.

20 2023 Proxy Statement graphic

TABLE OF CONTENTS

Human Capital Management

The key focus areas of our ESG strategy are the following:

graphic
Creating Opportunity:
With usersover 2,500 team members in over 180more than 90 countries around the world, at Upwork we are changing the way work gets done by placingintentionally designing our people processes with independent talent at our core. As pioneers of the heartfuture of every business. We operate the world’s largest work, marketplace that connects businesses with independent talent, as measured by GSV. Our mission—to create economic opportunities so people have better lives—is integral to how we operate, promote our culture, hiring practices, and talent development, build products, and lead our industry.
Business Ethics, Integrity, and Governance: From our board of directors to every team member, the work we do each day is guided by a robust business ethics and integrity program that encourages everyone to always do the right thing. Integrity is embedded in our culture and something we promote from the top down and throughout our business. These values similarly extend to our work marketplace, where we understand there is a certain level of responsibility that comes with connecting independent professionals to clients and new opportunities through our work marketplace. Through our trust and safety programs, we have developed tools and instituted policies to promote responsible, safe, and transparent interactions between our independent professionals and clients. In compliance with the UK Modern Slavery Act 2015, we publish an annual statement detailing our efforts to combat modern slavery and human trafficking, which is available on our website at upwork.com/documents/uk-transparency-statement.
Our Team: We are committed to creating and supporting an inclusive environment that promotes and encourages diversity, belonging, wellness, and career development. This commitment extends to all aspects of our relationships with our team members, including in the hiring and promotion process, training, benefits, and career development. For more information regarding our efforts to support and engage with our team members, see “Upwork’s Approach to Human Capital Management.”
Sustainability: We believe in combating climate change, and we are committed to protectingdelivering a world class experience to the environment. By enabling remote work, and through our purchaseworkforce of carbon offsets and renewable energy credits, we first achieved carbon neutrality for 2019 and are committed to remaining carbon neutral going forward. Our business model and practices, including enabling remote work—which we estimate enabled our team members to avoid one million commuting miles in 2019—have allowed us to reduce our greenhouse gas emissions and carbon footprint. We again achieved carbon neutrality for 2020.the future.”

Sunita Solao
Chief People Officer

For more information regarding our corporate responsibility and sustainability programs, see our 2020 Annual Impact Report in the “Investor Relations” section of our website, which is located at investors.upwork.com. In the report, which is not part of our proxy solicitation materials, we report in more detail on Upwork’s corporate responsibility and sustainability programs and ESG efforts.

Upwork’s Approach to Human Capital Management

Board of Directors Oversight

Our board of directors recognizes the critical importance of our team and the necessity to ensure a diverse, inclusive, and creative work environment that is centered around a values-based culture. Our board of directors meets regularly with management to discuss issues impacting our team members and to focus on ways to support our workforce. Our focus on culture comes from our board of directors and flows throughout our company. In evaluating our Chief Executive Officer and management team, significant emphasis is put on their contributions to our overall culture.

Our Team and Culture

Our mission—to create economic opportunities so people have better lives—is integral to our culture and how we build amazing teams and products to lead our industry. We enable remote work not only through our work marketplace for our users but also for our own team members andfor whom we are proud to do so, notably for its positiveoffer a remote-first work model, which has environmental, contributions, among a host ofas well as other, reasons.benefits. Our strength is in our hybrid team approach, consistingconsists of corporate employees, independent talent we engage through our work marketplace, and freelancers.advisors. Our team members are distributed around the world, and while we have corporate offices, we do not solely rely on in-person collaboration. Our team works with a variety of tools and has adopted practices to ensure all voices are heard, innovation is fostered, and results are achieved. Our hybrid team, and its belief in our mission, values, and values,vision, is critical to our success. With the consistent investment in the development of our team and our commitment to diversity, inclusion, and belonging, we cultivate an environment where people are able to be themselves at work and perform to the best of their abilities.

21 

Our People

We

Our mission not only drives the creation and continuous development of our work marketplace; it is also integral to how we engage our workforce in meaningful waysemployees and take timely action in responseour approach to their feedback.creating and fostering an inclusive environment that promotes and encourages diversity, inclusion, belonging, career development, and wellness. As of December 31, 2022, we had approximately 850 employees, and throughout 2022, we engaged approximately 1,950 independent team members through our work marketplace to provide services to us on a variety of internal projects. We surveybelieve the positive relationship between us and our team members on a regular basis to gather feedback, and in 2020 had an employee response rateour unique, strong culture differentiate us and are key drivers of 86%. Our average employee satisfaction score was 79, which is six points above our industry benchmark.

Our company values are:

Inspire a boundless future of work;
Put our community first;
Have a bias toward action; and
Build amazing teams.

business success.

Diversity, Inclusion, and Belonging

We put our people and their experiences first. In 2020, we took a strong stance internally and externally to reinforce our commitment to being an antiracist company.

We view belonging as a feeling, inclusion as a practice, and diversity as an outcome.

We foster belonging through our employee resource Upwork Belonging Communities—groups and listening sessions that build empathy and promote skill-building education.inclusive skill-building. We cultivate inclusion by equipping managers with tools to effectively build and lead amazing and inclusive teams that amplify team members’ voices. Additionally, we practice multi-dimensionalmultidimensional compensation and mobility reviews during our semi-annual employee performance evaluation process. This is led by a cross-functional team of human resource and legal leaders to help ensure we are fair in our rewards and recognition strategy. To bolster our diversity, inclusion, and belonging efforts, we also utilizeconduct an internal transfer review board to help ensurefacilitate equity in internal mobility practices throughout our company as an ongoing priority. Diversity, inclusion, and belonging is a journey, not a destination, and, as such, we will continue to explore ways to cultivate an inclusive culture where every team member feels that they belong.belongs.
graphic2023 Proxy Statement 21

TABLE OF CONTENTS

Training and Development

As an organization built on talent and skills development, we understand the value of providing our employees with ongoing professional development and leadership opportunities so that they can advance their careers. Led by our dedicated learning and development team, we offer our team members an array of learning and development opportunities, including a variety of in-person and online training sessions and workshops.

Benefits and Competitive Compensation

Beyond our training and development efforts, we take pride in offering competitive, market-based

We strive to offer market-competitive compensation and benefits.benefits to attract and retain employees for the long term. We engage compensation consultants to benchmark our employee compensation with external sources to ensure fair and equitable pay practices,practices. We provide total rewards that attract and alignment of our executiveretain world-class employees through a total compensation package that includes equity-based awards to align employee compensation with stockholder interests. Merit increases and promotions are rewarded based on an individual’s impact within the organization and an established business need, and in consideration with market data. Knowing our employees have diverse needs and life priorities, we also provide expandedcomprehensive benefits and services to those eligible, which include core benefits such as medical, dental, vision, and visiondisability insurance, in addition to benefits tailored to the specific needs of our employees, such as mental health, fertility, family back-up care, and adoption support. We also supportoffer a health savings account with company contributions, family and encourage ourmedical leave, flexible working schedules, paid holidays and flexible vacation policies. We sponsor a 401(k) plan that includes a matching contribution, offer financial coaching through a third-party provider, and maintain an employee stock purchase plan that enables eligible employees to give backpurchase shares of our stock at a discount through payroll deductions.
Organizational Wellbeing
We engage our workforce in meaningful ways and take timely action in response to their feedback. Research into workforce experience begins during onboarding and is sustained throughout a team member’s tenure at Upwork. This “life cycle” approach to workforce research affords our communities by giving each employee two days a yearsenior leadership and human resources team members ongoing and real-time insight into critical moments of “Volunteer Time Off”worker experience and productivity. The collection of such data allows leadership, line managers, and our human resources team to dedicateidentify successes and opportunities at myriad levels, including for individual team members, company-wide programs, and larger organizational units. Over time, the aggregation and analysis of such data enables us to the causesoptimize for those workforce factors that matter most to them, as well as opportunities to engage in community volunteer efforts both in persondrive crucial people and remotely throughout the year.

22 
business outcomes.

Employee Wellness

Employee safety and well-beingwellbeing is of paramount importance to us in any year and was of particular focus in 2020 in light of the COVID-19 pandemic.us. We provide productivity and collaboration tools and resources for employees, working remotely, including training and toolkitstool kits to help leaders effectively lead and manage remote teams. In addition, we enhanced and promotedpromote programs to support our employees’ physical, financial, and mental well-being.wellbeing. For example, we regularly conduct internal surveys to assess the well-beingwellbeing and needs of our employees, and we significantly expandedoffer employee assistance and mindfulness programs to help employees and their families manage anxiety, stress, sleep, and overall well-being.

wellbeing. Additionally, we believe that our employees are at their best when they take the time to recharge. In order to encourage our employees to recharge and make their wellbeing a priority, we provide unlimited paid time off in addition to our company-recognized holidays.
Delinquent Section 16(a) Reports
Section 16(a) of the Exchange Act requires our directors, executive officers, and any persons who own more than 10% of our common stock to file initial reports of ownership and reports of changes in ownership with the SEC. Based solely on our review of the forms filed with the SEC and written representations from our directors and executive officers, we believe that all Section 16(a) filing requirements were timely met in the year ended December 31, 2022, with the following exceptions: (i) Ms. Brown filed a Form 4 on February 23, 2022 that inadvertently omitted the grant of 121,765 restricted stock units, which was corrected with the filing of an amended Form 4 on February 24, 2022; (ii) Mr. Gilpin filed a Form 4 on February 23, 2022 that inadvertently omitted the grant of 62,785 restricted stock units, which was corrected with the filing of an amended Form 4 on February 24, 2022; and (iii) Mr. McCombs filed a Form 4 on February 23, 2022 that inadvertently omitted the grant of 114,155 restricted stock units, which was corrected with the filing of an amended Form 4 on February 24, 2022.
23 
22 2023 Proxy Statement graphic


NOMINATIONS PROCESS AND DIRECTOR QUALIFICATIONS

TABLE OF CONTENTS

Nominations Process and Director Qualifications
Nomination to the Board of Directors

Candidates for nomination to our board of directors are selected by our board of directors based on the recommendation of our nominating and governance committee in accordance with the committee’s charter, our restated certificate of incorporation and amended and restated bylaws, our Corporate Governance Guidelines, and the criteria approved by our board of directors regarding director candidate qualifications. In identifying and recommending candidates for nomination, the nominating and governance committee considers candidates recommended by directors, officers, employees, stockholders, and others, using the same criteria to evaluate all candidates. Evaluations of candidates generally involve a review of background materials, internal discussions, and interviews with selected candidates as appropriate, and in addition, the committee may engage consultants or third-party search firms to assist in identifying and evaluating potential nominees.

With respect to disclosure requirements, nominees for director nominated by a third party are not expected to provide additional disclosure compared to nominees for director nominated by the nominating and governance committee.

Stockholders wishing to recommend candidates for consideration by our nominating and governance committee should submit their recommendations to the attention of the Corporate Secretary at our mailing address contained elsewhere in this Proxy Statement. Information regarding the process for submitting stockholder nominations for candidates for membership on our board of directors is set forth below under “Stockholder Proposals to Be Presented at the Next Annual MeetingFrequently Asked Questions.”

Director Qualifications

With the goal of developing a diverse, experienced, and highly qualified board of directors, our nominating and governance committee is responsible for developing and recommending to our board of directors the desired qualifications, expertise, and characteristics of members of our board of directors, including any specific minimum qualifications that the committee believes must be met by a committee-recommended nominee for membership on our board of directors and any specific qualities or skills that the committee believes are necessary for one or more of the members of our board of directors to possess.

Because the identification, evaluation, and selection of qualified directors is a complex and subjective process that requires consideration of many intangible factors and will be significantly influenced by the particular needs of our board of directors from time to time, our board of directors has not adopted a specific set of minimum qualifications, qualities, or skills that are necessary for a nominee to possess, other than those that are necessary to meet U.S. legal, regulatory, and Nasdaq listing requirements and the provisions of our restated certificate of incorporation, our amended and restated bylaws, our Corporate Governance Guidelines, and the charters of the committees of our board of directors. In addition, neither our board of directors nor our nominating and governance committee has a formal policy with regard to the consideration of diversity in identifying nominees. When considering nominees, the nominating and governance committee may take into consideration many factors including, among other things, a candidate’s independence, integrity, diversity, skills, financial and other expertise, breadth of experience, knowledge about our business or industry, and ability to devote adequate time and effort to responsibilities of our board of directors in the context of its existing composition. Through the nomination process, our nominating and governance committee seeks to promote board membership that reflects a diversity of business experience, expertise, viewpoints, personal backgrounds, and other characteristics that are expected to contribute to our board of directors’ overall effectiveness. The brief biographical description of each director set forth in Proposal No. 1 below includes the primary individual experience, qualifications, attributes, and skills of each of our directors that led to the conclusion that each director should serve as a member of our board of directors at this time.
graphic2023 Proxy Statement 23

TABLE OF CONTENTS

Board Evaluations

We conduct an annual self-evaluation process for our board of directors and its committees. As part of this process, each member of our board of directors individually meets with outside counsel to discuss their assessment of the performance of the board of directors and its committees, their own performance, and the performance of fellow members of the board of directors. The chairperson of our board of directors shares feedback received with individual members of the board of directors, with the nominating and governance committee, and with the full board of directors. Our board of directors then reviews and discusses the feedback.

24 

Our board evaluation process is used:

by our board of directors and nominating and governance committee to assess the current composition of our board of directors and its committees and make recommendations for the qualifications, expertise, and characteristics we should seek in identifying potential new directors;
by our board of directors and nominating and governance committee to identify the strengths and areas of opportunity of each member of our board of directors and to provide insight into how each member of our board of directors can be most valuable;
to improve agenda topics of the board of directors and its committees so that information they receive enables them to effectively address the issues they consider most critical; and
by our nominating and governance committee as part of its annual review of each director’s performance when considering whether to nominate the director for re-election to the board of directors.
by our board of directors and nominating and governance committee to assess the current composition of our board of directors and its committees and to make recommendations for the qualifications, expertise, and characteristics we should seek in identifying potential new directors;
by our board of directors and nominating and governance committee to identify the strengths and areas of opportunity of each member of our board of directors and to provide insight into how each member of our board of directors can be most valuable;
to improve agenda topics of the board of directors and its committees so that information they receive enables them to effectively address the issues they consider most critical; and
by our nominating and governance committee as part of its annual review of each director’s performance when considering whether to nominate the director for re-election to the board of directors.
25 
24 2023 Proxy Statement graphic


PROPOSAL NO.

TABLE OF CONTENTS

Proposal 1

ELECTION OF DIRECTORS


Election of Directors
Our board of directors currently consists of eight directors and is divided into three classes. Each class serves for three years, with the terms of office of the respective classes expiring in successive years. Directors in Class IIIII will stand for election at the Annual Meeting. The terms of office of directors in Class IIII and Class III do not expire until the annual meetings of stockholders held in 20222024 and 2023,2025, respectively. At the recommendation of our nominating and governance committee, our board of directors proposes that each of the Class IIIII nominees named below, each of whom is currently serving as a director in Class III,II, be elected as a Class IIIII director for a three-year term expiring at the 20242026 annual meeting of stockholders and until such director’s successor is elected and qualified, or until such director’s earlier death, resignation, disqualification, or removal.

Shares represented by proxies will

We have a majority voting standard for uncontested elections of directors, which means that to be voted “FOR” the election of eachelected, a director nominee must receive a majority of the nominees named below, unlessvotes cast. This means the proxy is marked to withhold authority to so vote.number of shares voted “FOR” a director nominee must exceed the votes cast “AGAINST” that nominee (with “abstentions” and “broker non-votes” not counted as a vote cast either “FOR” or “AGAINST” that director’s election). If any nominee for any reason is unable to serve or for good cause will not serve, the proxies may be voted for such substitute nominee as the proxy holder might determine. Each nominee has consented to being named in this Proxy Statement and to serve if elected. Proxies may not be voted for more than threetwo directors. Stockholders may not cumulate votes for the election of directors.

Nominees to Our Board of Directors

The nominees and their age, occupation, and length of service on our board of directors as of March 31, 2021,2023, are provided in the table below and in the additional biographical descriptions set forth in the text below the table.

Name of Director/Nomineeand Experience
Age
Age
Position
Director
Since
Independent
Committee Memberships
Class III Directors:
Leela Srinivasan
Former Chief Marketing Officer, Momentive Global Inc. (maker of SurveyMonkey)
49
July 2019
Yes
Audit
Hayden Brown
Gary Steele
Chief Executive Officer, Splunk Inc.
39
60
President,
August 2018
Yes
Compensation
graphic2023 Proxy Statement 25

TABLE OF CONTENTS

graphic
Committees: audit

Other Public Company Boards: none

Experience: Leela Srinivasan has served as a member of our board of directors since July 2019. Ms. Srinivasan is an experienced Chief Marketing Officer with specific expertise in the human resources technology sector. Most recently, Ms. Srinivasan served as Chief Marketing Officer of Checkout Ltd, a global payments provider also known as Checkout.com, from September 2021 to March 2023. Previously, Ms. Srinivasan served as Chief Marketing Officer of Momentive Global Inc. (formerly known as SurveyMonkey), an online agile experience management company, from April 2018 to September 2021. Prior to that, she served as Chief Marketing Officer at Lever, Inc., a recruiting software company, from September 2015 to March 2018. Prior to Lever, Inc., Ms. Srinivasan served as VP of Marketing at OpenTable, Inc., an online restaurant booking company, from June 2014 to September 2015. Prior to OpenTable, Ms. Srinivasan served in marketing positions at LinkedIn Corporation from January 2010 to May 2014. Ms. Srinivasan also spent three years in management consulting at Bain & Company in San Francisco and London, and five years in sales at Business Wire, a Berkshire Hathaway company. Ms. Srinivasan holds an M.A. in History and English Literature from the University of Edinburgh and earned an M.B.A. from the Tuck School of Business at Dartmouth, where she is a member of the Board of Advisors.

Relevant Expertise: Ms. Srinivasan brings to our board of directors her extensive leadership, executive, and business-to-business marketing experience gained across multiple organizations, including Momentive Global Inc., a publicly traded company. Ms. Srinivasan’s experience spans multiple relevant aspects of marketing including field marketing, online/digital marketing, corporate communications, global customer programs, advertising, campaigns, events, and corporate and employer branding. She has also spent multiple years in the human resources technology sector and has relevant experience in the payments sector.
Leela Srinivasan
Former Chief Marketing Officer, Momentive Global Inc. (maker of SurveyMonkey)
graphic
Committees: compensation

Other Public Company Boards: Splunk Inc.

Experience: Gary Steele has served as a member of our board of directors since August 2018. Mr. Steele has served as the Chief Executive Officer and Director
December 2019as a member of the board of directors of Splunk Inc., a data platform for security and observability, since April 2022. Mr. Steele also currently serves on the board of directors of two privately held companies. Prior to joining Splunk Inc., Mr. Steele served as the Chief Executive Officer of Proofpoint, Inc., an enterprise security company, from 2002 to March 2022. Prior to that, Mr. Steele served from June 1997 to July 2002 as the Chief Executive Officer of Portera Systems Inc., a software company. Before Portera, Mr. Steele served as the Vice President and General Manager of the Middleware and Data Warehousing Product Group at Sybase, Inc., an enterprise and mobile software company. Mr. Steele’s prior experience includes business development, marketing, and engineering roles at Sun Microsystems, Inc. and Hewlett-Packard Company, computer, computer software, and information technology companies. Mr. Steele holds a B.S. in Computer Science from Washington State University.

Relevant Expertise: Mr. Steele brings to our board of directors valuable business experience managing a public company, as well as extensive knowledge of advising technology companies.
Gary Steele
Chief Executive Officer, Splunk Inc.
OUR BOARD OF DIRECTORS RECOMMENDS A VOTE “FOR” THE ELECTION OF EACH OF THE TWO NOMINATED DIRECTORS
26 2023 Proxy Statement graphic

TABLE OF CONTENTS

Continuing Directors
The directors who are serving terms that end following the Annual Meeting and their age, occupation, and length of service on our board of directors as of March 31, 2023, are provided in the table below and in the additional biographical descriptions set forth in the text below the table.
Name and Experience
Age
Director Since7
Independent
Committee Memberships
Class III Directors
Hayden Brown
President and Chief Executive Officer, Upwork Inc.
41
December 2019
No
Gregory C. Gretsch(1)(2)
Founding Partner and Managing Director, Jackson Square Ventures
54
56
Director
March 2014
Yes
Compensation and Audit
Anilu Vazquez-Ubarri(3)
Board Member and Chief Human Resources Officer, TPG Inc.
44
46
Director
November 2020
Yes
Compensation
Class I Directors
Kevin Harvey
Founder and General Partner, Benchmark Capital
58
March 2014
Yes
Nominating and Governance
Thomas Layton
Former Chief Executive Officer, OpenTable, Inc.
60
March 2014
Yes
Nominating and Governance
Elizabeth Nelson
Former Executive Vice President and Chief Financial Officer, Macromedia, Inc.
62
February 2015
Yes
Audit and Nominating and Governance
(1)
graphic
Member of the audit committee
(2)Member of the compensation committee
(3)Member of the
Committees: nominating and governance committee(Chair)

Other Public Company Boards: none

Experience: Thomas Layton has served as a member of our board of directors and chairperson since our inception in March 2014. Prior to that, Mr. Layton served as a member of the board of directors of oDesk from May 2006 to March 2014 and as chairperson from December 2011 to March 2014. Mr. Layton currently serves on the board of directors of several private companies. Previously, Mr. Layton served in various leadership roles, including as the Chief Executive Officer of OpenTable, Inc., an online restaurant reservation company, from 2001 to 2007 and as the Chief Executive Officer of Metaweb Technologies, Inc., a data infrastructure company, from 2007 to 2010. Mr. Layton holds a B.S. from the University of North Carolina at Chapel Hill and an M.B.A. from the Stanford Graduate School of Business.

Relevant Expertise: Mr. Layton brings to our board of directors extensive leadership experience, gained from his experience advising and managing technology companies. Moreover, he brings historical knowledge, operational expertise, and continuity to our board of directors.
Thomas Layton Former Chief Executive Officer, OpenTable, Inc.

7
Does not include service on the board of directors of Elance, Inc., which we refer to as Elance, or oDesk Corporation, which we refer to as oDesk, prior to the combination of the two companies in March 2014.
graphic2023 Proxy Statement 27

TABLE OF CONTENTS

graphic
Committees: none

Other Public Company Boards: none

Experience: Hayden Brown

Hayden Brown has served as a member of our board of directors since December 2019. Ms. Brown has served as our President and Chief Executive Officer since January 2020, and previously served as our Chief Marketing and Product Officer from April 2019 to December 2019, as our Senior Vice President, Product and Design from January 2016 to April 2019, as our Vice President, Head of Product from January 2015 to January 2016, and as our Vice President and Senior Director Marketplace since our inception in March 2014. Prior to that, Ms. Brown served in numerous product leadership roles, starting when she joined oDesk as a Director of Marketplace in December 2011. Prior to joining us, Ms. Brown was Vice President of Corporate Development at LivePerson, Inc., an online messaging, marketing, and analytics company, from September 2010 to November 2011. Ms. Brown also worked for Microsoft Corporation, a technology company, as Director of Corporate Strategy and M&A from January 2010 to September 2010 and as Senior Strategy Manager from June 2007 to January 2010. Ms. Brown began her career as a Business Analyst at McKinsey & Company, a business management consulting firm, in its New York office. Ms. Brown holds an A.B. in Politics from Princeton University. We believe that

Relevant Expertise: Ms. Brown should serve as a member ofbrings to our board of directors due to the perspective she bringsher extensive leadership experience, including as our Chief Executive Officer, her extensive leadership experience, and her institutional knowledge of our company.company, understanding of our company culture, and familiarity with developing and executing our strategic priorities.
Hayden Brown
President and Chief Executive Officer, Upwork Inc.

26 
graphic

Gregory C. Gretsch

Committees: compensation (Chair) and audit

Other Public Company Boards: none

Experience: Gregory C. Gretsch has served as a member of our board of directors since our inception in March 2014 and as a member of the board of directors of oDesk from 2004 to March 2014. Mr. Gretsch is a founding partner and has served as Managing Director of Jackson Square Ventures, a venture capital firm, since 2011. Mr. Gretsch also serves on the board of directors of several private companies, and he served as a director of Responsys, Inc. from 2001 to 2014. Mr. Gretsch has also served as a managing director at Sigma Partners, a venture capital firm, since 2001. Mr. Gretsch holds a B.B.A. in Management Information Systems from the University of Georgia. We believe that

Relevant Expertise: Mr. Gretsch should serve as a member ofbrings to our board of directors based on his significant experience in the venture capital industry analyzing, investing in, and serving on the boards of directors of other technology companies and hisentrepreneurial, management, and leadership experience as a former founder and executive of several startup technology companies, and his background analyzing, investing in, and serving on the boards of directors of other technology companies.
Gregory C. Gretsch
Founding Partner and Managing Director, Jackson Square Ventures
graphic
Committees: nominating and governance

Other Public Company Boards: none

Experience: Kevin Harvey has served as a member of our board of directors since our inception in March 2014. Prior to that, Mr. Harvey served as a member of the board of directors of oDesk from August 2006 to March 2014. Previously, Mr. Harvey served on the board of directors of Proofpoint, Inc. until August 2021. Mr. Harvey is a founder and general partner of Benchmark Capital, a venture capital firm, which he co-founded in 1995. Before founding Benchmark, Mr. Harvey was founder, President, and Chief Executive Officer of Approach Software Corp., a server database company. Before founding Approach Software, Mr. Harvey founded Styleware, Inc., a software company. Mr. Harvey holds a B.S. in Engineering from Rice University.

Relevant Expertise: Mr. Harvey brings to our board of directors his significant experience investing in and serving on the boards of directors of other technology companies, as well as his management and leadership experience as a founder and former executive of multiple startup technology companies.

Kevin Harvey Founder and General Partner, Benchmark Capital
28 2023 Proxy Statement graphic

TABLE OF CONTENTS

graphic
Committees: audit (Chair) and nominating and governance

Other Public Company Boards: PhenomeX Inc.

Experience: Elizabeth Nelson has served as a member of our board of directors since February 2015. Ms. Nelson currently serves on the board of PhenomeX Inc., a functional cell biology company, as well as several private companies. Ms. Nelson’s public company board of directors service includes serving as a director of Virgin Group Acquisition Corp. II from March 2021 to June 2022, Nokia Corporation from 2012 to 2021, Zendesk, Inc. from 2013 to 2019, and Pandora Media, Inc. from July 2013 to June 2017. From 1996 through 2005, Ms. Nelson served as the Executive Vice President and Chief Financial Officer of Macromedia, Inc., where she also served as a director from January 2005 to December 2005. Ms. Nelson holds a B.S. in Foreign Service from Georgetown University, an M.B.A. in Finance from the Wharton School at the University of Pennsylvania, and also earned the NACD’s CERT Certificate in Cybersecurity Oversight.

Relevant Expertise: Ms. Nelson brings to our board of directors her extensive experience in advising technology companies and a deep understanding of the financial, accounting, and operational aspects of executive management from her prior experience as an executive of numerous public and private technology companies.
Elizabeth Nelson
Former Executive Vice President and Chief Financial Officer, Macromedia, Inc.
graphic
Committees: compensation

Other Public Company Boards: TPG Inc.

Experience: Anilu Vazquez-Ubarri

Anilu Vazquez-Ubarri has served as a member of our board of directors since November 2020. Ms. Vazquez-Ubarri has servedcurrently serves as Chief Human Resources Officer and is a member of the board of directors of TPG Global, LLC,Inc., a global private investment firm, since August 2018. Shewhere she made Partner in 2019. Ms. Vazquez-Ubarri also serves on the board of directors of Greenhouse Software, Inc., a hiring software company. Previously, she served in a variety of roles at The Goldman Sachs Group, Inc., a multinational investment bank and financial services company, from 2007 through 2018, including as Chief Diversity Officer and Global Head of Talent beginning in 2014. Prior to that, Ms. Vazquez-Ubarri served as an associate in the executive compensation and employee benefits group at Shearman & Sterling LLP. Ms. Vazquez-Ubarri holds a J.D. from the Fordham University School of Law and an A.B, cum laude, in History and Latin American Studies from Princeton University. We believe that

Relevant Expertise: Ms. Vazquez-Ubarri should serve as a member ofbrings to our board of directors based on her extensive leadershipvaluable knowledge of human resources and talentemployment aspects of executive management, experience.

OUR BOARD OF DIRECTORS RECOMMENDS A VOTE “FOR ALL NOMINEES” IN THE ELECTION OF EACH OF THE THREE NOMINATED DIRECTORS

27 

Continuing Directors

The directors who are serving for terms that end following the Annual Meeting and their age, occupation, and length of service on our board of directors as of March 31, 2021, are provided in the table below and in the additional biographical descriptions set forth in the text below the table.

Name of DirectorAgePositionDirector Since
Class I Directors:
Kevin Harvey(1)56DirectorMarch 2014
Thomas Layton(1)58ChairpersonMarch 2014
Elizabeth Nelson(2)(3)60DirectorFebruary 2015
Class II Directors:
Leela Srinivasan(2)47DirectorJuly 2019
Gary Steele(3)58DirectorAugust 2018

(1)Member of the nominating and governance committee
(2)Member of the audit committee
(3)Member of the compensation committee

Kevin Harvey

Kevin Harvey has served as a member of our board of directors since our inception in March 2014. Prior to that, Mr. Harvey served as a member of the board of directors of oDesk from August 2006 to March 2014. Mr. Harvey currently serves on the board of directors of Proofpoint, Inc. Mr. Harvey is a founder and general partner of Benchmark Capital, a venture capital firm, which he co-founded in 1995. Before founding Benchmark, Mr. Harvey was founder, President, and Chief Executive Officer of Approach Software Corp., a server database company. Before founding Approach Software, Mr. Harvey founded Styleware, Inc., a software company. Mr. Harvey holds a B.S. in Engineering from Rice University. We believe that Mr. Harvey should serve as a member of our board of directors based on his significant experience investing in and serving on the boards of directors of other technology companies as well as hisoperational and risk management experience from her roles at global investment entities. She also brings her experience handling talent and leadership experience as a founder and former executive of multiple startup technology companies.

diversity issues directly for multinational organizations.
Anilu Vazquez-Ubarri
Board Member and Chief Human Resources Officer, TPG Inc.

Thomas Layton

Thomas Layton has served as a member of our board of directors and chairperson since our inception in March 2014. Prior to that, Mr. Layton served as a member of the board of directors of oDesk from May 2006 to March 2014 and as chairperson from December 2011 to March 2014. Mr. Layton currently serves on the board of directors of several private companies. Previously, Mr. Layton served in various leadership roles, including as the Chief Executive Officer of OpenTable, Inc., an online restaurant reservation company, from 2001 to 2007 and as the Chief Executive Officer of Metaweb Technologies, Inc., a data infrastructure company, from 2007 to 2010. Mr. Layton holds a B.S. from the University of North Carolina at Chapel Hill and an M.B.A. from the Stanford Graduate School of Business. We believe that Mr. Layton should serve as a member of our board of directors based on his extensive leadership experience. He also brings historical knowledge, operational expertise, and continuity to our board of directors.

28 
graphic2023 Proxy Statement 29

Elizabeth Nelson

Elizabeth Nelson has served as a member of our board of directors since February 2015. Ms. Nelson currently serves on the boards of Berkeley Lights, Inc., a digital cell biology company, and Virgin Group Acquisition Corp. II, a blank check company incorporated for the purpose of effecting a business combination, as well as several private companies. Ms. Nelson’s public company board of directors service includes serving as a director of Nokia Corporation from 2012 to 2021, Zendesk, Inc. from 2013 to 2019, Pandora Media, Inc. from July 2013 to June 2017, Ancestry.com Inc. from 2009 to 2012, SuccessFactors, Inc. from 2007 to 2012, Autodesk, Inc. from 2007 to 2010, CNET Networks, Inc. from 2003 to 2008, and Brightcove Inc. from 2010 to 2014. From 1996 to 2005, Ms. Nelson served as the Executive Vice President and Chief Financial Officer of Macromedia, Inc., where she also served as a director from January 2005 to December 2005. Ms. Nelson holds a B.S. in Foreign Service from Georgetown University and an M.B.A. in Finance from the Wharton School at the University of Pennsylvania. We believe that Ms. Nelson should serve as a member of our board of directors due to her financial, accounting, and operational expertise from prior experience as an executive and director for numerous public and private technology companies.

Leela Srinivasan

Leela Srinivasan has served as a member of our board of directors since July 2019. Ms. Srinivasan has served as Chief Marketing Officer of SVMK Inc., an online survey company also known as SurveyMonkey, since April 2018. Previously, she served as Chief Marketing Officer at Lever, Inc., a recruiting software company, from September 2015 to March 2018. Prior to that, Ms. Srinivasan served as VP of Marketing at OpenTable, Inc., an online restaurant booking company, from June 2014 to September 2015. Prior to OpenTable, Ms. Srinivasan served in marketing positions at LinkedIn Corporation from January 2010 to May 2014. Ms. Srinivasan also spent three years in management consulting at Bain & Company in San Francisco and London, and five years in sales at Business Wire, a Berkshire Hathaway company. Ms. Srinivasan holds an M.A. in History and English Literature from the University of Edinburgh and earned an M.B.A. from the Tuck School of Business at Dartmouth, where she serves on the M.B.A. Advisory Council. We believe that Ms. Srinivasan should serve as a member of our board of directors based on her extensive leadership, executive, and business-to-business marketing experience gained across multiple organizations including SurveyMonkey, a publicly traded company. Ms. Srinivasan’s experience spans multiple relevant aspects of marketing including field marketing, online/digital marketing, corporate communications, global customer programs, advertising, campaigns, events, and corporate and employer branding.

Gary Steele

Gary Steele has served as a member of our board of directors since August 2018. Mr. Steele has served as the Chief Executive Officer and as a member of the board of directors of Proofpoint, Inc., an enterprise security company, since 2002. Mr. Steele also currently serves on the board of directors of two privately held companies. Prior to joining Proofpoint, Mr. Steele served from June 1997 to July 2002 as the Chief Executive Officer of Portera Systems Inc., a software company. Before Portera, Mr. Steele served as the Vice President and General Manager of the Middleware and Data Warehousing Product Group at Sybase, Inc., an enterprise and mobile software company. Mr. Steele’s prior experience includes business development, marketing, and engineering roles at Sun Microsystems, Inc. and Hewlett-Packard Company, computer, computer software, and information technology companies. Mr. Steele holds a B.S. in Computer Science from Washington State University. We believe that Mr. Steele should serve as a member of our board of directors based on his extensive management and leadership experience.

TABLE OF CONTENTS

29 

Director Expertise, Experience, and Attributes

Our board of directors is comprised ofcomprises a diverse mix of directors with complementary expertise, experience, and attributes, as summarized in the table below. Our directors may also have experience or attributes in addition to what is reflected in the table below.

graphic
30 2023 Proxy Statement graphic

TABLE OF CONTENTS

graphic
8
SummaryAge and tenure is as of Expertise, Experience, and Attributes

Technology and Product Development

Experience inMarch 31, 2023. Tenure does not include service on the technology industry and in managementboard of technology companies and/directors of Elance or experience in product development, including engineering and design

CEO and Management Experience

Experience in executive management positions

Compensation / Talent Management

Experience in compensation, organizational management, leadership, talent development, and identifying, recruiting, and motivating top talent

Other Public Company Board Experience

Experience on other public company boards

Corporate Governance

Experience providing oversight of governance at a public company, including ethics, corporate responsibility, and protection of stockholder interests

Finance

Experience in leadership of a financial firm or managementoDesk prior to the combination of the finance function of an enterprise

Marketing and Product

Experiencetwo companies in marketing and leadership of corporate marketing functions or experience in product development

International

Experience with global businesses, operations, strategy, and/or customer bases

Operations

Current or former executive with significant operating experience, who is able to provide insight into developing, implementing, and assessing an enterprise’s operating plan, business, and strategy

Risk Management

Experience in overseeing risk management and understanding risks, including, for example, environmental and social risks, faced by enterprise operations

Strategic Planning

Experience in providing insight into developing, implementing, and assessing businesses and strategy

March 2014. All other demographics are based on each director’s self-identification.

30 
graphic2023 Proxy Statement 31

 
Demographics[1]
Age
Years5839545660475844
Tenure
Years1411614712<1
Gender
Female    
Male    
Non-Binary        
Race/Ethnicity
Asian (including South Asian)       
Black or African American        
Hispanic or Latino       
Native Hawaiian or Pacific Islander        
Native American or Alaska Native        
White��
Did Not Wish to Identify        

TABLE OF CONTENTS

7 Age and tenure is as of March 31, 2021. Gender and race/ethnicity is based on each director’s self-identification.

31 

Board Composition

We also believe that our current board of directors’ composition represents an effective balance with respect to director tenure and age. Recent director additions provide our board of directors with fresh perspectives and diverse experiences, while directors with longer tenure provide continuity and valuable insight into our business and strategy. The matrix above and charts below provide information regarding the tenure and age distribution of our board of directors (as of March 31, 2021)2023). We define tenure as including service on the board of directors of Elance or oDesk prior to the combination of the two companies in March 2014.

We are committed to creating a diverse and inclusive culture, which starts at the top with our board of directors. Four of our eight directors are women, two directors self-identify as being racially or ethnically diverse, and one director self-identifies as LGBTQ+, all. All of whomour directors bring unique experiences and backgroundbackgrounds to Upwork.

graphic
32 2023 Proxy Statement graphic


2020

TABLE OF CONTENTS

2022 Director Compensation

The following table provides information for 20202022 regarding all compensation awarded to, earned by, or paid to each person who served as a director for some portion or all of 2020,2022, other than Ms. Brown, our President and Chief Executive Officer. Ms. Brown is not included in the table below as she is an employee and received no additional compensation for her service as a director during 2020.2022. The compensation received by Ms. Brown as an employee is shown in the “Executive Compensation—20202022 Summary Compensation Table” below.

NameFees Earned or Paid in Cash ($)Stock Awards ($)(1)Total ($)(2)
Thomas Layton(3)5,000216,129221,129
Gregory C. Gretsch(4)20,000195,043215,043
Kevin Harvey(5)2,500195,043197,543
Daniel Marriott(6)9,375195,043204,418
Elizabeth Nelson(7)60,000158,144218,144
Leela Srinivasan(8)39,375158,144197,519
Gary Steele(9)5,000195,043200,043
Anilu Vazquez-Ubarri(10)9,375532,324541,699

Name
Fees Earned or Paid in Cash ($)(1)
Stock Awards ($)(2)
Total ($)(2)
Thomas Layton(3)
8,250
329,218
337,468
Gregory C. Gretsch(4)
28,750
263,382
292,132
Kevin Harvey(5)
4,150
263,382
267,532
Elizabeth Nelson(6)
87,275
203,025
290,300
Leela Srinivasan(7)
68,750
203,025
271,775
Gary Steele(8)
7,000
263,382
270,382
Anilu Vazquez-Ubarri(9)
61,375
203,025
264,400
(1)
The amounts reported in this column for certain members of our board of directors may be lower than those of the other members of our board of directors because of the different compensation arrangements based on elections to receive fees or awards in cash or equity or based on additional fees payable on account of committee membership, as further described in “Non-Employee Director Compensation Arrangements.”
(2)
The amounts reported in these columns represent the aggregate grant date fair value of RSUs awarded to directors in 20202022 computed in accordance with Financial Accounting Standard Board Accounting Standards Codification Topic 718, which we refer to as ASC 718. This amount doesThe number of RSUs that a director receives is calculated by dividing the target value of the RSU award by the 30-day trailing average trading price. Accordingly, the amounts reported in this column do not reflect the actual economic value realized by the director, which will vary depending on the performance of our common stock. Members of our board of directors may elect to receive a portion of their compensation in cash consideration in lieu of RSUs, with any such cash consideration having equal economic value on the date of grant as the RSUs that a director would have otherwise received.RSUs.
(2)The amounts reported in this column for certain members of our board of directors may be lower than those of the other members of our board of directors because of their election to receive cash consideration in lieu of RSUs for the components of director compensation for which there is an election. While the actual economic value of any cash received is equal on the date of grant to the RSUs that a director would have otherwise received, the amounts reported above may vary depending on the performance of our common stock, and may be higher in the event our stock price increases leading up to the grant date.
(3)
As of December 31, 2020,2022, Mr. Layton held 15,32713,360 unvested RSUs, which included the Annual Award, the Non-Executive Chairperson Fee, and the Fee (RSU), as further described in (and which vest in accordance with the vesting schedule described under) “Non-Employee Director Compensation Arrangements.”
(4)
As of December 31, 2022, Mr. Gretsch held 11,707 unvested RSUs, which included both the Annual Award and the Fee (RSU), as further described in (and which vest in accordance with the vesting schedule described under) “Non-EmployeeNon-Employee Director Compensation Arrangements.Arrangements.
(5)
(4)
As of December 31, 2020,2022, Mr. GretschHarvey held 14,46311,707 unvested RSUs, which included both the Annual Award and the Fee (RSU), as further described in (and which vest in accordance with the vesting schedule described under) “Non-EmployeeNon-Employee Director Compensation Arrangements.Arrangements.
(6)
(5)
As of December 31, 2020, Mr. Harvey2022, Ms. Nelson held 14,46310,192 unvested RSUs, which included bothrepresented the Annual Award, and the Fee (RSU), asoptions to purchase 295,000 shares of common stock. The RSUs are further described in (and which vest in accordance with the vesting schedule described under) “Non-EmployeeNon-Employee Director Compensation Arrangements.”
(6)Mr. Marriott resigned from our board of directors on November 10, 2020.
(7)As of December 31, 2020, Ms. Nelson held 12,952 RSUs, which represented the Annual Award. The RSUs are further described in, and vest in accordance with, the vesting schedule described below under “Non-Employee Director Compensation Arrangements—Annual Award.Arrangements.” The stock option was fully vested and exercisable as of December 31, 2020,2022, and expires 10 years after the date of grant.on February 25, 2025.
(7)
(8)
As of December 31, 2020,2022, Ms. Srinivasan held 25,87210,192 unvested RSUs, which included both the Initial Award granted to Ms. Srinivasan upon her appointment to our board of directors in July 2019 andrepresented the Annual Award, as further described in (and which vest in accordance with the vesting schedule described under) “Non-EmployeeNon-Employee Director Compensation Arrangements.Arrangements.
(8)
(9)
As of December 31, 2020,2022, Mr. Steele held 14,463 RSUs. The11,707 unvested RSUs, which included both the Annual Award and the Fee (RSU), asand options to purchase 150,527 shares of common stock. The RSUs are further described in (and which vest in accordance with the vesting schedule described under) “Non-EmployeeNon-Employee Director Compensation Arrangements.Arrangements. The stock option was fully vested and exercisable as of December 31, 2022, and expires on August 19, 2028.
(9)
(10)  
As of December 31, 2020,2022, Ms. Vazquez-Ubarri held 19,61414,947 unvested RSUs, which included both the Initial Award granted to Ms. Vazquez-Ubarri upon her appointment to our board of directors in November 2020 and the Annual Award, as further described in (and which vest in accordance with the vesting schedule described under) “Non-EmployeeNon-Employee Director Compensation Arrangements.Arrangements.

graphic2023 Proxy Statement 33

TABLE OF CONTENTS

Non-Employee Director Compensation Arrangements

In July 2019,order to remain competitive in an increasingly challenging landscape for recruitment of non-employee directors, our board of directors approved an amended and restated non-employee director compensation program.program in April 2022. Under thesuch amended and restated non-employee director compensation program, non-employee directors were entitled to receive an increase in the amount of certain compensation. The following changes were made to the program: (i) an increase to the Annual Award (as defined below) from $170,000 to $185,000, (ii) an increase to the Chairperson Fee (as defined below) from $40,000 to $60,000, and (iii) an increase in the following cashannual committee chair and equity compensation:

member fees: (A) audit committee chair fee from $20,000 to $35,000 and audit committee member fee from $10,000 to $17,500, (B) compensation committee member fee from $6,500 to $7,500, and (C) nominating and governance committee chair fee from $8,000 to $8,500 and nominating and governance committee member fee from $4,000 to $4,300. Our current amended and restated non-employee director compensation program is as follows:

Equity Compensation—Initial Award

Upon initial appointment or election to our board of directors, each new non-employee director appointed or elected to our board of directors will be granted RSUs under our 2018 Equity Incentive Plan, which we refer to as the 2018 Plan, with a total value of $300,000$400,000 based on a 30-day trailing average trading price, which we refer to as the Initial Award. The grant date fair value of the Initial Award shall not exceed $1,000,000 in a calendar year when combined with the aggregate grant date fair value of any other equity award(s) and cash compensation received by such non-employee director for service on our board of directors for such calendar year.

The Initial Award will be granted effective on the date of the non-employee director’s initial appointment or election to our board of directors, which we refer to as the Initial Award Grant Date.

The Initial Award will vest with respect to one-third of the total number of RSUs subject to the Initial Award each year beginning with the date that is one year followingthe one-year anniversary of the Initial Award Grant Date, in each case, so long as the non-employee director continues to provide services as a non-employee director to us through such date. The final annual installment of the Initial Award will fully vest on the earlier of (i) the date immediately prior to our annual meeting of stockholders in the last full year of the vesting of the Initial Award and (ii) the date that is the last day of the last full year of the vesting of such grant, in each case, so long as the non-employee director continues to provide services as a non-employee director to us through such date.

The Initial Award will accelerate in full immediately prior to the consummation of a “corporate transaction” (as defined in the 2018 Plan).
34 2023 Proxy Statement graphic

TABLE OF CONTENTS

Cash or Equity Compensation Election—Annual Award

Each non-employee director will automatically be entitled to an annual award of a $150,000$185,000 cash payment or RSUs with a total value of $150,000$185,000 based on a 30-day trailing average trading price, which we refer to as the Annual Award. The Annual Award will be payable in the form of RSUs or, at a non-employee director’s election, in cash.

The initial Annual Award, to the extent payable in RSUs and consistent with the applicable election made, will be granted automatically on the date of the non-employee director’s initial appointment or election to our board of directors, which we refer to as the Initial Annual Award Grant Date, and will be pro-rated for partial quarters served. Subsequently, the Annual Award, to the extent payable in RSUs, will be granted automatically on the date of our annual meeting of stockholders for each year thereafter, which we refer to as the Annual Award Grant Date.

The Annual Award will fully vest, or in the case of cash will be paid, on the earlier of (i) the date immediately prior to our next annual meeting of stockholders and (ii) the date that is one year following the Initial Annual Award Grant Date or Annual Award Grant Date, as the case may be, so long as the non-employee director continues to provide services as a non-employee director to us through such date. The Annual Award will be paid, in the case of cash, or settle,settled, in the case of RSUs, in the same calendar year in which the Annual Award vests.

The Annual Award (regardless of the form of payment) will accelerate in full immediately prior to the consummation of a “corporate transaction” (as defined in the 2018 Plan).

Cash or Equity Compensation—Annual General Board Service Fee, Board Non-Executive Chairperson Fee, and Board Lead Independent Director Fee

Annual compensation payable to (i) each non-employee director as a general board service fee is $35,000,$55,000, which we refer to as the General Board Service Fee, (ii) the non-executive chairperson as a chairperson fee is $20,000,$60,000, which we refer to as the Chairperson Fee, and (iii) the lead independent director as a lead independent director fee is $15,000, we refer to each fee in clauses (i)-(iii), as a Fee, each of which is pro-rated for partial quarters served and payable in cash or, at a non-employee director’s election, in the form of RSUs.

34 

If the non-employee director elects to receive the Fee in cash, which we refer to as the Fee (Cash), it will be paid quarterly in arrears (with the first such payment in any event occurring on the last day of the first calendar quarter following the date of the director’s appointment or election to our board of directors), in each case, so long as the non-employee director continues to provide services in the applicable capacity to us through such date.

If the non-employee director elects to receive the Fee in RSUs, which we refer to as the Fee (RSU), the initial Fee (RSU) will be granted automatically on the date of the director’s initial appointment or election to our board of directors and each subsequent Fee (RSU) will be granted automatically on the date of our annual meeting of stockholders for each year thereafter. The number of shares subject to the applicable Fee (RSU) will be based on a 30-day trailing average trading price (which will be pro-rated for partial quarters served in the relevant capacity). The Fee (RSU) will vest and settle quarterly (with the first such vesting and settlement date occurring on the last day of the first calendar quarter following the date of the non-employee director’s appointment or election to our board of directors), in each case, so long as the non-employee director continues to provide services in the applicable capacity to us through such date.

The Fee (regardless of the form of payment) will accelerate in full immediately prior to the consummation of a “corporate transaction” (as defined in the 2018 Plan).

The final quarterly installment of each Fee (Cash) or the Fee (RSU), as applicable, will fully vest on the earlier of (i) the date immediately prior to our next annual meeting of stockholders and (ii) the date that is the last day of the last full quarter of the vesting of such grant, in each case, so long as the non-employee director continues to provide services in the applicable capacity to us through such date.
graphic2023 Proxy Statement 35

TABLE OF CONTENTS

Non-Employee Director Cash Compensation

In addition to the General Board Service Fee, each non-employee director is entitled to receive additional annual cash compensation for committee membership as follows:

Audit committee chair: $20,000
Audit committee member: $10,000
Compensation committee chair: $10,000
Compensation committee member: $5,000
Nominating and governance committee chair: $5,000
Nominating and governance committee member: $2,500

Audit committee chair: $35,000
Audit committee member: $17,500
Compensation committee chair: $15,000
Compensation committee member: $7,500
Nominating and governance committee chair: $8,500
Nominating and governance committee member: $4,300
Chairs of our committees receive the cash compensation designated above for chairs in lieu of the non-chair member cash compensation.

The cash compensation designated above will be paid quarterly in arrears, for so long as the non-employee director continues to provide services in the applicable non-employee director capacity to us through such date, and will be pro-rated for partial quarters served. The final quarterly installment of each such annual fee will be paid on the earliest of (i) the date of our next annual meeting of stockholders, (ii) the date immediately prior to our next annual meeting of stockholders if the applicable non-employee director’s service as a director ends at such meeting due to the director’s failure to be re-elected or the director not standing for re-election, and (iii) the date that is the last day of the last full quarter of such installment, in each case, so long as the non-employee director continues to provide services in the applicable capacity to us through such date.

35 
36 2023 Proxy Statement graphic

TABLE OF CONTENTS

Proposal 2

2021 Amended and Restated Non-Employee Director Compensation Program

In order to remain competitive in an increasingly challenging landscape for recruitment

Ratification of non-employee directors, in April 2021, our boardAppointment of directors approved an amended and restated non-employee director compensation program, to take effect with respect to 2021. Under such amended and restated non-employee director compensation program, non-employee directors will be entitled to receive an increase in the amount of certain compensation provided under our current non-employee director compensation program described above. This increase will result in the following: (i) Initial Award with a total value of $400,000 based on a 30-day trailing average trading price, (ii) Annual Award with a total value of $170,000 (if payable in RSUs, based on a 30-day trailing average trading price), (iii) General Board Service Fee of $55,000 (if payable in RSUs, based on a 30-day trailing average trading price), and (iv) Chairperson Fee of $40,000 (if payable in RSUs, based on a 30-day trailing average trading price). Additionally, this increase will result in the following annual fees for committee memberships: (i) audit committee chair fee of $20,000 and audit committee member fee of $10,000, (ii) compensation committee chair fee of $15,000 and compensation committee member fee of $6,500, and (iii) nominating and governance committee chair fee of $8,000 and nominating and governance committee member fee of $4,000.

36 
Independent Registered Public Accounting Firm

PROPOSAL NO. 2

RATIFICATION OF APPOINTMENT OF INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM

Our audit committee has selected PricewaterhouseCoopers LLP as our independent registered public accounting firm to perform the audits of our consolidated financial statements and our internal control over financial reporting for the year ending December 31, 2021,2023, and recommends that stockholders vote for ratification of such selection. The ratification of the selection of PricewaterhouseCoopers LLP as our independent registered public accounting firm for the year ending December 31, 2021,2023, requires the affirmative vote of a majority of the voting power of the shares present or represented by proxy at the Annual Meeting.Meeting and voting affirmatively or negatively on the proposal. In the event that PricewaterhouseCoopers LLP is not ratified by our stockholders, the audit committee will review its future selection of PricewaterhouseCoopers LLP as our independent registered public accounting firm. Further, the audit committee may select a different independent registered public accounting firm at any time if, in the committee’s sole discretion, the committee determines that such a change would be in the best interests of our company and stockholders.

PricewaterhouseCoopers LLP audited our consolidated financial statements and our internal control over financial reporting for the year ended December 31, 2020.2022. Representatives of PricewaterhouseCoopers LLP are expected to be present at the Annual Meeting, and they will be given an opportunity to make a statement at the Annual Meeting if they desire to do so and will be available to respond to appropriate questions.

Independent Registered Public Accounting Firm Fees and Services

We regularly review the services and fees from our independent registered public accounting firm. These services and fees are also reviewed with our audit committee annually. In accordance with standard policy, PricewaterhouseCoopers LLP periodically rotates the individuals who are responsible for our audit.

In addition to performing the audit of our consolidated financial statements and our internal control over financial reporting, PricewaterhouseCoopers LLP provided various other services during the years ended December 31, 20192021 and 2020.2022. Our audit committee has determined that PricewaterhouseCoopers LLP’s provision of these services, which are described below, does not impair PricewaterhouseCoopers LLP’s independence from us. During the years ended December 31, 20192021 and 2020,2022, fees for services provided by PricewaterhouseCoopers LLP were as follows (in thousands):

Fees Billed to Upwork20192020
Audit fees(1)$3,270$2,168
Audit-related fees(2) 12 
Tax fees(3)  
All other fees(4) 2 3
Total fees$3,284$2,171

Fees Billed to Upwork
2021
2022
Audit fees(1)
​$2,623
​$2,913
Audit-related fees
Tax fees(2)
35
All other fees(3)
4
     4
Total fees
$2,662
$2,917
(1)
“Audit fees” include fees for audit services primarily related to: the audit of our annual consolidated financial statements and attestation services related to compliance with the Sarbanes-Oxley Act of 2002; the review of our quarterly condensed consolidated financial statements; comfort letters, consents, and assistance with and review of documents filed with the SEC; and other services normally provided in connection with statutory and regulatory filings.
(2)“Audit-related fees” include fees for financial reporting consultation and research.
(3)
“Tax fees” include fees for tax compliance and advice. Tax advice fees encompass a variety of permissible tax services, including technical tax advice related to federal and state income tax matters, assistance with sales tax, and assistance with tax audits.matters.

(4)(3)
“All other fees” include fees for annual subscription services for access to online accounting research and disclosure checklist software applications.

graphic2023 Proxy Statement 37

TABLE OF CONTENTS

Policy on Audit Committee Pre-Approval of Audit and Permissible Non-Audit Services of Independent Registered Public Accounting Firm

Our audit committee’s policy is to pre-approve all audit and permissible non-audit services provided by the independent registered public accounting firm, the scope of services provided by the independent registered public accounting firm, and the fees for the services to be performed. These services may include audit services, audit-related services, tax services, and other services. Pre-approval is detailed as to the particular service or category of services and is generally subject to a specific budget. The independent registered public accounting firm and management are required to periodically report to the audit committee regarding the extent of services provided by the independent registered public accounting firm in accordance with this pre-approval, and the fees for the services performed to date.

All of the services relating to the fees described in the table above were approved by our audit committee.

OUR BOARD OF DIRECTORS AND AUDIT COMMITTEE RECOMMEND A VOTE FOR” FORTHE RATIFICATION OF THE APPOINTMENT OF PRICEWATERHOUSECOOPERS LLP AS OUR INDEPENDENT REGISTERED PUBLIC ACCOUNTING FIRM FOR THE YEAR ENDING DECEMBER 31, 2021

2023.
38 2023 Proxy Statement graphic


PROPOSAL NO.

TABLE OF CONTENTS

Proposal 3

ADVISORY VOTE ON THE COMPENSATION OF OUR NAMED EXECUTIVE OFFICERS


Advisory Vote on the Compensation of Our Named Executive Officers
In accordance with the rulesSection 14A of the SEC,Exchange Act, we are providing stockholders with an opportunity to make a non-binding advisory vote on the compensation of our Named Executive Officers. This non-binding advisory vote is commonly referred to as a “say-on-pay”Say-on-Pay vote. The non-binding advisory vote on the compensation of our Named Executive Officers, as disclosed in this Proxy Statement, will be determined by the vote of a majority of the voting power of the shares present or represented at the Annual Meeting and voting affirmatively or negatively on the proposal.

Stockholders are urged to read the “Executive Compensation” section of this Proxy Statement, which discusses how our executive compensation policies and procedures implement our compensation philosophy and contains tabular information and narrative discussion about the compensation of our Named Executive Officers. Our compensation committee and our board of directors believe that these policies and procedures are effective in implementing our compensation philosophy and in achieving our goals. Accordingly, we ask our stockholders to vote “FOR”FOR the following resolution at the Annual Meeting:

“RESOLVED, that our stockholders approve, on a non-binding advisory basis, the compensation of the Named Executive Officers, as disclosed in the Proxy Statement pursuant to Item 402 of Regulation S-K, including the Compensation Discussion and Analysis, the compensation tables and narrative discussion, and the other related disclosures.”

As an advisory vote, this proposal is not binding. However, our board of directors and compensation committee, which is responsible for designing and administering our executive compensation program, value the opinions expressed by stockholders in their vote on this proposal and will consider the outcome of the vote when making future compensation decisions for our Named Executive Officers.

OUR BOARD OF DIRECTORS RECOMMENDS A VOTE FOR”FOR APPROVAL, ON A NON-BINDING ADVISORY BASIS, OF THE COMPENSATION OF OUR NAMED EXECUTIVE OFFICERS

OFFICERS.
graphic2023 Proxy Statement 39


SECURITY OWNERSHIP

TABLE OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENTCONTENTS

Proposal 4
Approval of Restated Certificate of Incorporation
We are proposing to amend and restate our current restated certificate of incorporation to make the changes described below.
Section 102(b)(7) of the DGCL was amended effective August 1, 2022 to permit a Delaware corporation’s certificate of incorporation to include a provision that limits or eliminates (i.e., exculpates) the monetary liability of certain officers for breaches of the fiduciary duty of care as officers in certain actions. This exculpation would not protect officers from liability for breach of the duty of loyalty, acts or omissions not in good faith or that involve intentional misconduct or a knowing violation of law, or any transaction in which the officer derived an improper personal benefit. Nor would this exculpation shield such officers from liability for claims brought by or in the right of the corporation, such as derivative claims. In addition, only certain officers may be exculpated from liability: (i) a corporation’s president, chief executive officer, chief operating officer, chief financial officer, chief legal officer, controller, treasurer, or chief accounting officer; (ii) an individual identified in public filings as one of the most highly compensated executive officers of the corporation; and (iii) an individual who, by written agreement with the corporation, has consented to be identified as an officer for purposes of Delaware’s long-arm jurisdiction statute. The amendment to our current restated certificate of incorporation proposed in this Proposal 4 would eliminate the liability of these statutorily defined officers as described above, but the amendment will not have retroactive effect and will not apply to any act or omission occurring prior to the effectiveness of the amendment. The amendment is not being proposed in response to any specific resignation, threat of resignation, or refusal to serve by any officer.
Our board of directors believes it is necessary to provide protection to officers to the fullest extent permitted by law in order to attract and retain highly qualified senior leadership. The nature of the role of directors and officers often requires them to make decisions on crucial matters in time-sensitive situations, which can create substantial risk of investigations, claims, actions, suits, or proceedings seeking to impose liability on the basis of hindsight, especially in the current litigious environment and regardless of merit. Limiting concern about personal risk would empower both directors and officers to best exercise their business judgment in furtherance of stockholder interests. We expect competitor companies will likely adopt exculpation clauses that limit the personal liability of officers in their charters, and failing to obtain approval of the Restated Certificate of Incorporation could negatively affect our ability to recruit and retain high-caliber officer candidates. This protection has long been afforded to directors, and our board of directors believes that extending similar exculpation to its officers is fair and in the best interests of our company and our stockholders.
In addition to the changes to permit officer exculpation described above, the amendment would make technical and administrative changes to the choice of forum provision in our current restated certificate of incorporation in order to (i) clarify that the federal district court for the District of Delaware shall be the sole and exclusive forum for certain claims in the event the Court of Chancery does not have jurisdiction, (ii) add a provision that all “internal corporate claims” (as defined in Section 115 of the DGCL) be brought exclusively in Delaware courts, and (iii) clarify that we shall be entitled to equitable relief to enforce the choice of forum provision.
Our board of directors has unanimously approved the Restated Certificate of Incorporation, in the form attached to this proxy statement as Appendix A-1, and recommends that our stockholders vote “FOR” the approval of the Restated Certificate of Incorporation. For convenience of reference, a copy of the Restated Certificate of Incorporation showing the changes from our current restated certificate of incorporation, with deleted text shown in strikethrough and added or moved text shown as underlined, is attached to this proxy statement as Appendix A-2.
The affirmative vote of the holders of a majority of the outstanding shares of our capital stock entitled to vote generally in the election of directors is required to approve the Restated Certificate of Incorporation. Shares that are voted “abstain” are treated the same as shares voting “against” this proposal.
40 2023 Proxy Statement graphic

TABLE OF CONTENTS

If our stockholders approve the Restated Certificate of Incorporation, our board of directors has authorized our officers to file the Restated Certificate of Incorporation with the Delaware Secretary of State, to become effective upon acceptance by the Delaware Secretary of State. Our board of directors intends to have that filing made if, and as soon as practicable after, this proposal is approved at this annual meeting. However, even if our stockholders adopt the Restated Certificate of Incorporation, our board of directors may abandon the Restated Certificate of Incorporation without further stockholder action prior to the effectiveness of the filing of the Restated Certificate of Incorporation with the Delaware Secretary of State and, if abandoned, the Restated Certificate of Incorporation will not become effective. If the board of directors abandons the Restated Certificate of Incorporation, it will publicly disclose that fact and the reason for its determination.
OUR BOARD OF DIRECTORS RECOMMENDS A VOTE “FOR” THE APPROVAL OF THE RESTATED CERTIFICATE OF INCORPORATION.
graphic2023 Proxy Statement 41

TABLE OF CONTENTS

Security Ownership of Certain Beneficial Owners and Management
The following table sets forth certain information with respect to the beneficial ownership of our common stock as of March 31, 2021,2023, by:

each of our Named Executive Officers;
each of our directors;
all of our directors and executive officers as a group; and
each stockholder known by us to be the beneficial owner of more than 5% of the outstanding shares of our common stock.

each of our Named Executive Officers;
each of our directors;
all of our directors and executive officers as a group; and
each stockholder known by us to be the beneficial owner of more than 5% of the outstanding shares of our common stock.
We have determined beneficial ownership in accordance with the rules of the SEC, and the information is not necessarily indicative of beneficial ownership for any other purpose. Except as indicated by the footnotes below, we believe, based on information furnished to us, that the persons and entities named in the table below have sole voting and sole dispositive power with respect to all shares beneficially owned, subject to applicable community property laws.

Applicable percentage ownership is based on 125,962,107133,464,264 shares of our common stock outstanding as of March 31, 2021.2023. The table below does not include Ms. Gessert, as her employment with the Company began after March 31, 2023. Shares of our common stock subject to stock options that are exercisable as of and within 60 days of March 31, 2021,2023, or RSUs that may vest and settle within 60 days of March 31, 2021,2023, are deemed to be outstanding and to be beneficially owned by the person holding the stock options or RSUs for the purpose of computing the percentage ownership of that person but are not treated as outstanding for the purpose of computing the percentage ownership of any other person. Unless otherwise indicated, the address of each of the individuals and entities listed in the table below is c/o Upwork Inc., 475 Brannan Street, Suite 430, San Francisco, California 94107.

NameNumber of Shares
Beneficially Owned
Percentage of Shares
Beneficially Owned (%)
Named Executive Officers and Directors:  
Hayden Brown(1)889,517*
Jeff McCombs(2)1,471*
Brian Kinion(3)47,423*
Eric Gilpin(4)199,293*
Gregory C. Gretsch(5)2,819,8952.2
Kevin Harvey(6)2,522,3092.0
Thomas Layton(7)4,314,0363.4
Elizabeth Nelson(8)695,027*
Leela Srinivasan10,173*
Gary Steele(9)173,357*
Anilu Vazquez-Ubarri
All executive officers and directors as a group (11 persons)(10)11,672,5019.2
Other 5% Stockholders:  
The Vanguard Group, Inc.(11)8,828,6197.0
T. Rowe Price Associates, Inc.(12)6,721,7215.3
BlackRock, Inc.(13)6,551,2455.2

40 

Name
Number of Shares
Beneficially Owned
Percentage of Shares
Beneficially Owned (%)
Named Executive Officers and Directors:
Hayden Brown(1)
1,269,331
*
Jeff McCombs(2)
97,264
*
Eric Gilpin(3)
290,373
*
Gregory C. Gretsch(4)
2,826,468
2.1
Kevin Harvey(5)
2,609,502
2.0
Thomas Layton(6)
4,120,216
3.1
Elizabeth Nelson(7)
679,096
*
Leela Srinivasan(8)
29,018
*
Gary Steele(9)
187,222
*
Anilu Vazquez-Ubarri(10)
18,928
*
All executive officers and directors as a group (10 persons)(11)
12,127,418
9.0
Other 5% Stockholders:
The Vanguard Group, Inc.(12)
11,105,458
8.3
BlackRock, Inc.(13)
8,750,581
6.6
Capital International Investors(14)
7,150,413
5.4
Baillie Gifford & Co.(15)
6,807,024
5.1
*
Less than 1%
(1)
Consists of (i) 465,362964,430 shares of common stock, (ii) 5,147 unvested restricted shares that will be released within 60 days of March 31, 2021, and (iii) 419,008261,709 shares of common stock subject to options held by Ms. Brown that are exercisable within 60 days of March 31, 2021.
(2)Consists2023, and (iii) 43,192 shares of 1,471 unvested restricted sharescommon stock subject to RSUs that will be releasedvest within 60 days of March 31, 2021.2023.
42 2023 Proxy Statement graphic

TABLE OF CONTENTS

(2)
Consists of 97,264 shares of common stock.
(3)Mr. Kinion served as our Chief Financial Officer until August 2020.
(4)
Consists of (i) 7,03351,188 shares of common stock, (ii) 7,260 unvested restricted shares that will be released within 60 days of March 31, 2021, and (iii) 185,000220,000 shares of common stock subject to options held by Mr. Gilpin that are exercisable within 60 days of March 31, 2021.2023, and (iii) 19,185 shares of common stock subject to RSUs that vest within 60 days of March 31, 2023.
(5)(4)
Consists of (i) 944,809228,899 shares of common stock held of record by Mr. Gretsch, (ii) 716,795 shares of common stock held by a trust for the benefit of Mr. Gretsch, (iii) 723,238 shares of common stock held of record byin a trust for the Gregory C. Gretsch Trust, UAD 1/28/00,benefit of which Mr. Gretsch is the trustee, (iii)and his spouse, (iv) 25,944 shares of common stock held of record by a trust for the benefit of Mr. Gretsch’sGretsch's children, (iv) 266,667and (v) 1,131,592 shares of common stock held of record by Martis Creek Investments, L.P. - Fund 3, (v) 95,000 shares of common stock held of record by Martis Creek Investments, L.P. - Fund 4, (vi) 769,925 shares of common stock held of record by Martis Creek Investments, L.P. - Fund 5, collectively, the Martis Creek entities, and (vii) 755 unvested restricted shares eligible to be released within 60 days of March 31, 2021. The Gretsch Revocable Trust, the general partner of the Martis Creek entities, has sole voting and dispositive power over such shares, and voting decisions with respect to such shares are madea limited partnership controlled by Mr. Gretsch. The address of the Martis Creek entities is 727 Sansome Street, Suite 300, San Francisco, California 94111.
(6)(5)
Consists of (i) 22,07544,195 shares of common stock held of record by Mr. Harvey, (ii) 748,164813,992 shares of common stock held of record by the Harvey Family Trust DTD 12/15/2000, of which Mr. Harvey is trustee, and (iii) 1,751,315 shares of common stock held of record by a limited liability company controlled by Mr. Harvey, and (iv) 755 unvested restricted shares eligible to be released within 60 days of March 31, 2021.Harvey.
(7)(6)
Consists of (i) 2,37412,330 shares of common stock held of record by Mr. Layton, (ii) 4,174,5643,971,975 shares of common stock held of record by Thomas H. Layton or Gabrielle M. Layton, or their successors, as trustees of the Layton Community Property Trust dated November 29, 1999, as amended, and (iii) 135,911 shares of common stock held of record by Mr. Layton as trustee of the Thomas HH. Layton Separate Property Revocable Trust dtd 11/29/99, and (iv) 1,187 unvested restricted shares eligible to be released within 60 days of March 31, 2021.which Mr. Layton serves as trustee.
(8)(7)
Consists of (i) 380,027384,096 shares of common stock held of record by the Nelson Family Trust and (ii) 315,000295,000 shares of common stock subject to stock options held by Ms. Nelson that are exercisable within 60 days of March 31, 2021.2023.
(8)
Represents 29,018 shares of common stock.
(9)
Consists of (i) 22,83036,695 shares of common stock held of record by Mr. Steele and (ii) 150,527 shares of common stock subject to options held by Mr. Steele that are exercisable within 60 days of March 31, 2021,2023.
(10)
Represents 18,928 shares of which 50,176 shares are unvested, but early exercisable within 60 days of March 31, 2021.common stock.
(10)(11)
Consists of (i) 10,586,39111,137,805 shares of common stock, (ii) 1,069,535927,236 shares of common stock subject to stock options that are exercisable within 60 days of March 31, 20212023 held by all our executive officers and directors as a group, and (iii) 62,377 shares of which 50,176 are unvested, but early exercisable,common stock subject to RSUs that vest within 60 days of March 31, 2021,2023 held by our executive officers and (iii) 16,575 unvested restricted shares that will be released within 60 days ofdirectors as a group. Does not include Ms. Gessert, as her employment with the Company began after March 31, 2021.2023.
(11)(12)
Based solely on information contained in a Schedule 13G/A filed with the SEC on February 10, 2021,9, 2023 by The Vanguard Group, Inc.Group. The Schedule 13G/A indicated that The Vanguard Group Inc. had shared voting power over 203,757 shares, sole dispositive power over 8,551,85810,787,378 shares, of our common stock, shared voting power over 208,597 shares of our common stock, and shared dispositive power over 276,761318,080 shares of our common stock. The address of The Vanguard Group Inc. is 100 Vanguard Blvd., Malvern, PA 19355.
(12)(13)
Based solely on information contained in a Schedule 13G/A filed with the SEC on February 1, 2023 by BlackRock, Inc. The Schedule 13G/A indicated that BlackRock, Inc. had sole voting power over 8,612,405 shares of our common stock and sole dispositive power over 8,750,581 shares of our common stock. The address of BlackRock, Inc. is 55 East 52nd Street, New York, NY 10055.
(14)
Based solely on information contained in a Schedule 13G filed with the SEC on February 16, 2021,13, 2023 by T. Rowe Price Associates, Inc.Capital International Investors. The Schedule 13G indicated that T. Rowe Price Associates, Inc.Capital International Investors had sole voting power over 1,544,024 shares of our common stock and sole dispositive power over 6,721,7217,150,413 shares of our common stock. The address of T. Rowe Price Associates, Inc.Capital International Investors is 100 E. Pratt333 South Hope Street, Baltimore, MD 21202.55th Fl, Los Angeles, CA 90071.
(13)(15)
Based solely on information contained in a Schedule 13G filed with the SEC on February 2, 2021,January 23, 2023 by BlackRock, Inc.Baillie Gifford & Co. The Schedule 13G indicated that BlackRock, Inc.Baillie Gifford & Co. had sole voting power over 6,452,6445,345,049 shares of our common stock and sole dispositive power over 6,551,2456,807,024 shares of our common stock. The address of BlackRock, Inc.Baillie Gifford & Co. is 55 East 52nd Street, New York, NY 10055.Calton Square, 1 Greenside Row, Edinburgh EH1 3AN, Scotland, UK.

41 
graphic2023 Proxy Statement 43


EXECUTIVE OFFICERS AND KEY EMPLOYEES

TABLE OF CONTENTS

Executive Officers and Key Employees
The names, ages, and positions of our executive officers and key employees their ages as of March 31, 2021, and their positions2023 (except as otherwise indicated) are shown below.

Name
Age
Age
Position
Executive Officers:

Hayden Brown
39
41
President, Chief Executive Officer, and Director
Jeff McCombs
Erica Gessert(1)
49
48
Chief Financial Officer
Eric Gilpin
42Senior Vice President,
44
Chief Sales Officer
Key Employees:

Lars Asbjornsen56Senior Vice President, Marketing
Sam Bright37Chief Product & Experience Officer
Zoë Harte46Chief People Officer
Brian Levey
53
55
Chief Business Affairs and Legal Officer & Secretary
Sunita Solao(2)
47
Chief People Officer
Melissa Waters
46
Chief Marketing Officer

(1)
Ms. Gessert’s employment with the Company began on April 25, 2023.
(2)
Ms. Solao’s employment with the Company began on April 25, 2023.

Our board of directors chooses executive officers, who then serve at the discretion of our board of directors. There is no family relationship between any of the directors or executive officers and any of our other directors or executive officers.

For information regarding Ms. Brown, please refer to Proposal No. 1 above.

Jeff McCombs

graphic
Jeff McCombs
Erica Gessert has served as our Chief Financial Officer since August 2020.April 2023. Prior to joining us, Mr. McCombsMs. Gessert served as the Chief Financial Officerin a number of Doctor On Demand,senior executive finance roles for PayPal Holdings, Inc., a virtual care provider, from October 2018 to August 2020. Prior to that, Mr. McCombs serveddigital payments and commerce company, including as Chief FinancialTransformation Officer of OpenTable, Inc., an online restaurant reservation company, from January 20162022 to March 2023, Senior Vice President of Finance & Analytics from June 2019 to January 2022, and Vice President of Finance & Analytics from March 2017 to June 2018, and as Chief Financial Officer of Flipboard2019. Before joining PayPal Holdings, Inc., a news and social network aggregation company, from May 2014 to May 2015. Mr. McCombs also previously in 2015, Ms. Gessert served as Head of Global Business Operations for the Ads business of Facebook, Inc., a social media conglomerate corporation, from August 2010 to May 2014, as Chief Financial Officer for Tumri Inc., an advertising platform, from March 2009 to July 2010, and in a variety of roles at Yahoo!for Sprint Corporation, a communications company, from 2009 to 2014, including as Vice President of Finance Operations, Postpaid Marketing and Chief Financial Officer, Sprint Prepaid from 2013 to 2014 and as Director of Investor Relations from 2011 to 2013. From 2007 to 2009, Ms. Gessert served as Director of Investor Relations for Virgin Mobile USA, Inc., including Senior Vice President, Business Operations, Vice President, Business Managementa wireless communications company. Ms. Gessert studied Economics and Director, Corporate Finance from April 2005Philosophy at Reed College.
Erica Gessert
graphic
Eric Gilpin has served as our Chief Sales Officer since February 2022. Prior to March 2009.that, Mr. McCombs holds a B.A. in Economics from the University of California, Los Angeles.

42 

Eric Gilpin

Eric Gilpin has served as our Senior Vice President, Sales sincefrom April 2016.2016 to February 2022. Prior to joining us, Mr. Gilpin served in a variety of roles for CareerBuilder, LLC, a human capital software provider and online employment website, including as President of Vertical Sales from September 2014 to March 2016, President of Staffing and Recruiting from November 2009 to September 2014, and Director of National Accounts from April 2004 to November 2009. Mr. Gilpin holds an M.B.A. from the Southern Methodist University’s Cox School of Business.
Eric Gilpin
Key Employees

Lars Asbjornsen

Lars Asbjornsen has served as our Senior Vice President, Marketing since May 2019. Prior to joining us, Mr. Asbjornsen served in a variety of marketing and business transformation roles for Robert Half International, a leading global specialized staffing provider, including Vice President of Digital Marketplace Solutions from January 2014 to May 2019, Vice President of Marketing Strategy and Technology from 2006 through 2013, and Vice President of Online Marketing and Recruiting from 2004 through 2006. Mr. Asbjornsen holds an M.B.A. from the University of San Diego School of Business.

Sam Bright

Sam Brighthas served as our Chief Product & Experience Officer since November 2020. Mr. Bright has served as an Advisory Council Member at the Smithsonian National Postal Museum since August 2019 and as an NACD Governance Fellow at the National Association of Corporate Directors since July 2019. Prior to joining us, Mr. Bright served in a variety of leadership roles at eBay Inc., including Vice President, General Manager from June 2018 to October 2020, and in roles in strategy, business development, and general management from 2012 to 2020. Mr. Bright holds a B.A. from Taylor University and an M.B.A. from Harvard Business School.

Zoë Harte

Zoë Harte has served as our Senior Vice President, Human Resources and Talent Innovation since September 2017. She previously served in roles as our Vice President and Head of Human Resources from March 2014 to August 2017 and as Head of Human Resources at oDesk from April 2013 to March 2014. Ms. Harte also worked at Rovi Corporation, a digital entertainment company, in senior human resources roles from 2008 to 2012. Prior to Rovi, Ms. Harte spent nine years at Yahoo! Inc. in a progression of human resources and customer care leadership roles. Ms. Harte holds a B.A. in Religion and Women’s Studies from Earlham College and an M.A. in Theology from the University of Exeter.

43 
44 2023 Proxy Statement graphic

TABLE OF CONTENTS

Key Employees

graphic
Brian Levey

Brian Levey has served as our Chief Business Affairs and Legal Officer and Secretary since October 2017. Prior to that, Mr. Levey served as our Chief Financial Officer from June 2015 to October 2017, as well as our General Counsel and Secretary since our inception in March 2014. Mr. Levey served as Vice President, General Counsel and Secretary of oDesk from June 2013 to March 2014. Prior to joining us, Mr. Levey served in a variety of roles at eBay Inc., including as Vice President, Deputy General Counsel and Assistant Secretary from 2006 to 2013, and, from 2000 to 2006, he served in increasingly senior legal roles at eBay.eBay Inc. He also previously served as Vice President, Legal at Metro-Goldwyn-Mayer Studios. Mr. Levey began his legal career with Latham & Watkins LLP. Mr. Levey holds an A.B. in Economics from Stanford University and a J.D. from Stanford Law School.
Brian Levey

graphic
Sunita Solao has served as our Chief People Officer since April 2023. Previously, she served as Vice President, People at Convoy, Inc., a digital freight network company, from October 2020 to May 2022. Prior to Convoy, Ms. Solao led the People team for Airbnb, Inc.’s Homes Business Division. Ms. Solao was at Airbnb, Inc. from May 2014 to September 2020. Before joining Airbnb, Inc., Ms. Solao was at eBay Inc., a global ecommerce company, from 2009 to 2014 where she held several human resources leadership roles. Ms. Solao holds a B.E. in Chemical Engineering from the Birla Institute of Technology and Science, Pilani, an M.B.A. in Human Resource Management from the University of Wisconsin-Madison, and an M.B.A. in Human Resources Management from Symbiosis International University.
Sunita Solao
graphic
Melissa Waters has served as our Chief Marketing Officer since December 2021. Prior to joining us, Ms. Waters served as Global Vice President of Marketing, Instagram, at Meta Platforms, Inc. from June 2020 to December 2021. Prior to joining Meta, Ms. Waters served as Chief Marketing Officer at Hims and Hers Health, Inc., a telehealth company, from April 2019 to May 2020, as VP, Marketing at Lyft, Inc., from October 2016 to November 2018, and a variety of roles in brand and marketing at Pandora Media, Inc., a streaming radio service, from December 2011 to October 2016, including VP, Brand and Product Marketing. Ms. Waters holds a B.A. from the University of Houston and an M.B.A. from Babson College.
Melissa Waters
44 
graphic2023 Proxy Statement 45


EXECUTIVE COMPENSATION

TABLE OF CONTENTS

Executive Compensation
Compensation Discussion and Analysis

This Compensation Discussion and Analysis describes the material elements of our executive compensation program during 20202022 and provides an overview of our executive compensation philosophy, including our principal compensation policies and practices. In addition, it analyzes how and why the compensation committee of our board of directors made the specific compensation decisions for our principal executive officer, each individual who served as our former principal financial officer, during 2020, and the executive officer (other than our principal executive officer and each individual who served as ourformer principal financial officer) who was our most highly-compensatedhighly compensated executive officer at the end of 2020, who2022, whom we refer to collectively as our Named Executive Officers.

For 2020,2022, our Named Executive Officers were:

Hayden Brown, our President and Chief Executive Officer;
Jeff McCombs, our Chief Financial Officer;
Eric Gilpin, our Senior Vice President, Sales; and
Brian Kinion, our former Chief Financial Officer.

Executive Transitions During 2020

In December 2019, our board of directors appointed Ms. Brown, our President and Chief Executive Officer, effective January 1, 2020.

who we refer to as our CEO;

Jeff McCombs, our former Chief Financial Officer; and
Eric Gilpin, our Chief Sales Officer.
Executive Transitions During 2022
Mr. Kinion resignedMcCombs’s final day as our Chief Financial Officer effective August 4, 2020. He remained employedwas December 31, 2022. On September 21, 2022, we entered into a Transition and Separation Agreement with us through October 2020, serving as an advisor to our Chief Executive Officer.

In July 2020, our board of directors appointed Mr. McCombs, as our Chief Financial Officer, effective August 4, 2020.

which is described in more detail below.

Compensation Discussion and Analysis Roadmap
Executive Summary
Summary of our key business and performance highlights, how we determine pay, stockholder outreach and engagement, and responsiveness to feedback
Executive Compensation Philosophy and Objectives
Description of our compensation philosophy and program
Compensation-Setting Process
How the compensation committee oversees our compensation program
Compensation Elements
Summary of our compensation program components and changes for 2023
Other Compensation Elements
Information on employee arrangements, additional policies, and tax and accounting considerations
Executive Summary

Who We Are

We operate the world’s largest work marketplace that connects businesses with independent talent from across the globe, as measured by GSV. During the year ended December 31, 2020,2022, our work marketplace enabled $2.5$4.1 billion of GSV. For freelancers we offerWe serve as a powerful discovery engine for talent, helping independent professionals and agencies find rewarding, engaging, and flexible work, as well as market their services and build their book of business. Talent benefit from access to quality clients and secure and timely payments while providingenjoying the freedom to run their own businesses, create their own schedules, and gainwork from their preferred locations. Moreover, talent have real-time visibility into high-demand opportunities.opportunities that are in high demand so that they can invest their time and focus on developing sought-after skills. For clients, we offerour work marketplace provides fast, secure, and efficient access to high-quality talent with overmore than 10,000 skills across more than 90125 categories.

Freelancers on our work marketplace include

Talent includes independent professionals and agencies of varying sizes and areis an increasingly sought-after, critical, and expanding segment of the global workforce. We define freelancers as users that advertise and provide services to clients through our work marketplace, and we define clients as users that work with freelancers through our work marketplace.

45 
46 2023 Proxy Statement graphic

TABLE OF CONTENTS

Key 20202022 Business Highlights

Despite the challenges of the COVID-19 pandemic, in 2020

In 2022, we launched a new generation of executive leadership and generated strong operational and financial results while advancing valuable strategic initiatives. Key business highlights from 20202022 include:

Performance Highlights
Growing Our Work Marketplace
GSV grew to $4.1 billion, a 16% year-over-year increase
Generating Strong Growth
Generated more than $618 million of revenue, a 23% year-over-year increase
Expanding Our Active Client Base(1)
Expanded the number of active clients by 6% year-over-year to approximately 814,000(2) while increasing GSV per active client 10% year-over-year to $5,045 in the fourth quarter of 2022
(1)
We define an active client as a client that has had spend activity on our work marketplace during the 12 months preceding the date of measurement. GSV per active client is calculated by dividing total GSV during the four quarters ended on the date of measurement by the number of active clients at the date of measurement.
(2)
As of December 31, 2022.
Strategic Highlights
Launching a New Generation of Leadership—Ms. Brown was appointed as
Continued to invest in the top talent necessary to drive our President and Chief Executive Officer, Jeff McCombs joined as our Chief Financial Officer, and Sam Bright joined as our Chief Product & Experience Officer.long-term success
Innovating the Work Marketplace
Developed an end-to-end solution that makes full-time hiring easily available to all clients

Launched Project Catalog Consultations and Project Tiers, Contract Workroom, MyStats, a Rate Calculator, enhancements to our Enterprise Suite, and paid promotional products such as Availability Badges and Boosted Proposals

Announced a partnership with Credly, a leading digital credential platform, to expand the number and breadth of certifications that can be verified on Upwork
Growing Our
Evangelizing the Work Marketplace
Increased our GSV grewinvestment in brand marketing, underscoring our conviction that this is a moment in time in which we can influence users meaningfully. In 2023, we plan to over $2.5 billion,reduce our investment in brand marketing given our efforts to become more efficient in the current macroeconomic environment

Launched our new campaign, “This Is How We Work Now,” with the goal of helping companies realize that “whom” you work with is a 21% year-over-year increase.much more powerful work transformation than “where” work gets done

Also launched Upwork Academy to help improve and diversify the skill set of talent on the platform and announced Opportunity Unlimited to connect professionals displaced from Ukraine with remote work opportunities
Scaling the Work Marketplace
Generating Strong Growth—we generated $373.6 million of revenue, a 24% year-over-year increase.
Expanding Our Core Client Base—we expanded
Increased the number of our core clients to over 145,000, while maintaining client spend retention of 102% as of December 31, 2020.
Launching and Expanding Initiatives to Drive Growth—we announced Project Catalog (pre-defined, ready-to-purchase projects) and expanded Direct Contacts (enabling invoicing and billing for hourly work).
Establishing Strategic Partnerships—among others, we announced a partnership with Zoom that integrates Zoom’s video and voice communication tools intospending $1 million or more on our work marketplace.marketplace by 45% compared to 2021
graphic2023 Proxy Statement 47

TABLE OF CONTENTS

We monitor GSV as a key financial and operational metric to evaluate our business, measure our performance, identify trends affecting our business, formulate business plans, and make strategic decisions. GSV is an important metric because it represents the amount of business transacted through our work marketplace. Moreover, we believe revenue is the primary measure of the performance of our business, as it provides comparability against competitors and is aligned to our strategic focus on growth objectives.

46 

Stockholder Value Creation

Driven by our strong financial and operational performance in 2020, we generated stockholder returns significantly exceeding those of the broader market (based on a comparison vs. the NASDAQ Composite Index) and overall technology sector (based on the NASDAQ 100 Technology Index).

The following charts show comparisons from October 3, 2018 (the date our common stock commenced trading on The Nasdaq Global Select Market) through March 31, 2021 and January 1, 2020 (the date on which Ms. Brown became our President and Chief Executive Officer) through March 31, 2021, of the cumulative total returns for our common stock, the NASDAQ 100 Technology Index, and the NASDAQ Composite Index, respectively. Such returns are based on historical results and are not intended to suggest future performance. The NASDAQ Composite Index and the NASDAQ 100 Technology Index assume reinvestment of any dividends.

Upwork’s Demonstrated Value Creation

47 
graphic

2020

2022 Core Compensation Elements

graphic
Generally, our executive compensation program consists of three principal elements – elements—annual base salary, annual bonus opportunities, and long-term incentive compensation opportunities in the form of equity awards:

Compensation Elements
Key Components
Objective and Alignment to Strategy
Base Salary
 Fixed cash
 Attract and retain top talent through market-competitive salary levels that are commensurate with the executive’s role and responsibility
Annual Bonus
 Variable payout based on
performance against pre-established targets

 Incentivize achievement of annual business objectives and reward short-term performance



• Compensation Program Revenue performance metric aligns
compensation with strategic growth
48 2023 Proxy Statement graphic

TABLE OF CONTENTS

Compensation Elements
Key Components
Objective and Alignment to Strategy
Long-Term Equity Incentives

 Time-based RSU awards, which vest over four-year period



• PSU awards, which are subject to both performance-based and time-based vesting requirements

 Align the interests of executives with stockholders



 Motivate long-term sustainable value creation



 Promote retention of top talent



• Incentivize achievement of annual business objectives and reward long-term performance

• Compensation Program Revenue performance metric aligns
compensation with strategic growth

Executive Compensation Policies and Practices

We endeavor to maintain sound governance standards consistent with our executive compensation policies and practices. The compensation committee evaluates our executive compensation program on at least an annual basis to ensure that it is consistent with our short-term and long-term goals given the dynamic nature of our business and the market in which we compete for executive talent. The following summarizes our executive compensation and related policies and practices:

Our Approach
Practices We Avoid
We maintain
Maintain an independent compensation committee and advisors.
We do not use “single-trigger” change in control benefits for our Named Executive Officers.advisors
We conduct
Conduct an annual executive compensation review.
We do not offer executive retirement plans.review
We emphasize
Emphasize a pay-for-performance philosophy.
We prohibit hedging of our equity securities by our employees, Named Executive Officers, and our board of directors.“pay-for-performance” philosophy
We maintain
Maintain stock ownership guidelines for our Named Executive Officers and members of our board of directors.
We do not provide reimbursements or gross ups for excise tax payments.directors
We maintain
Maintain a compensation recoupment and forfeiture, policy, or clawback, policy.policy
Ensure succession planning
Practices We doAvoid
Do not use “single-trigger” change in control benefits for our Named Executive Officers
Do not offer executive retirement plans
Prohibit hedging of our equity securities by our employees, including our Named Executive Officers, and the members of our board of directors
Do not provide reimbursements or “gross ups” for excise tax payments
Do not provide excessive perquisites for our Named Executive Officers.
We ensure succession planning.Officers

48 

ChiefAdvisory Vote on Named Executive Officer Performance Award

Our board of directorsCompensation and compensation committee determined that Ms. Brown demonstrated outstanding and exceptional capabilities in her first year as President and Chief Executive Officer, including leading our company as our share price appreciated more than 200% in 2020. Accordingly, our board of directors granted Ms. Brown an additional incentive commensurate with the level of achievement and ambition she had demonstrated as President and Chief Executive Officer. The incentive also promotes her retention in a highly competitive market for this level of leadership capability. In January 2021, the compensation committee granted Ms. Brown the CEO Performance Award, which has both service- and performance-based vesting requirements.

The CEO Performance Award is structured to protect stockholder interests and has a performance-based vesting component that requires achievement of extremely rigorous stock price hurdles, which promotes the alignment of Ms. Brown’s interests with those of stockholders and underscores our board of directors’ confidence in both Ms. Brown and our company. At the time of the award, our shares were trading near all-time high prices—following significant share price appreciation in 2020 under Ms. Brown’s leadership—and the lowest performance threshold requires an increase in share price of approximately 55% relative to the exercise price of the CEO Performance Award, and the majority of the award’s value will be earned only if the most rigorous goals are achieved. Additionally, achievement of any performance threshold is evaluated based on a 90-day volume-based weighted average price of our common stock to ensure that a short-term increase in share price was not treated as achievement of the intended long-term goals. The service-based vesting requirement provides for vesting of earned awards over a four-year period, which increases the value of the award in supporting retention.

The CEO Performance Award is described under the heading “CEO Performance Award for Ms. Brown” below.

Stockholder Engagement

At our 20202022 annual meeting of stockholders, we held a non-binding, advisory Say-on-Pay vote on the compensation of our 2021 Named Executive Officers, which we refer to as a “Say-on-Pay” vote, and approximately 90.8%Officers. Approximately 70.9% of the votes cast (for and against) approved our executive compensation programSay-on-Pay proposal for 2019. While we also received high levelsthe 2021 fiscal year. Our board of directors noted that stockholder support for such Say-on-Pay vote was substantially lower than the 96.3% support for the other proposals subjectSay-on-Pay vote at our annual meeting of stockholders in 2021.
graphic2023 Proxy Statement 49

TABLE OF CONTENTS

In response to vote,the decline in support, our board of directors and management team led a dedicated effort in the second half of 2022 to engage with our largest stockholders to discuss topics related to our executive compensation program and their votes on our Say-on-Pay proposal. Our strategy, the composition of the board of directors, corporate governance, and environmental and social practices were also discussed.
The compensation committee chair and the audit committee chair participated in select meetings and engaged directly with stockholders about the foregoing topics. A summary of such stockholder outreach and engagement efforts is included in the graphic below.
Stockholder Engagement
graphic
Source: Capital IQ; representing percentage of outstanding shares as of January 17, 2023, based on the latest ownership filings.
Overall, the feedback we heard from our stockholders was supportive of our broad executive compensation practices and such stockholders did not request any significant changes to our ongoing compensation program. Nearly all of the stockholders with which we spoke that voted against our Say-on-Pay proposal in 2022 attributed their votes to the CEO Performance Award that the compensation committee granted in 2021. A summary of the CEO Performance Award can be found under the heading “Chief Executive Officer Performance Award” in our 2022 proxy statement filed with the SEC on April 19, 2022. However, most stockholders noted that they understood and supported the compensation committee’s rationale for the award: to retain and motivate our CEO amid a very competitive market for executive talent in the technology industry. Furthermore, stockholders recognized the performance criteria associated with the CEO Performance Award were very rigorous and that the award would result in realized compensation for our CEO only if stockholders also realized significant value in the form of stock price appreciation. Stockholders were clear that they did not expect us to revisit or revise the CEO Performance Award; however, some stockholders inquired about whether this type of award would be granted as a regular feature of our ordinary-course executive compensation program, noting their general opposition to one-time awards and their expectation that they be used only in rare circumstances where the compensation committee has a compelling rationale.
Stockholders also expressed support for our increase in the percentage allocation of PSU awards in our long-term incentive compensation program in 2022. This change had been made, in part, in response to stockholder feedback.
In February 2023, the compensation committee increased the percentage allocation of PSUs that comprise Mr. Steele’s re-election was lower than 80%Gilpin’s long-term incentive compensation opportunity. The compensation committee believes this helps incentivize long-term value creation and sought to better understand stockholder views through direct dialogue.

strong financial performance and further align Mr. Gilpin’s compensation with the interests of our stockholders. Beginning in 2023, all of our Named Executive Officers' target PSU allocations will make up at least half of their overall goal long-term incentive opportunity.

Our board of directors and the compensation committee will continue to consider the result of the Say-on-Pay vote, as well as feedback received throughout the year, when making compensation decisions for our Named Executive Officers, as we value the opinions of our stockholders.stockholders’ opinions. In addition, consistent with the recommendation of our board of directors and the preference of our stockholders as reflected in the non-binding, advisory vote on the frequency of future Say-on-Pay votes held at our 2020 annual meeting of stockholders, we intend to hold an annuala Say-on-Pay vote every year. This policy will remain in effect until the next stockholder vote on the frequency of non-binding, advisory votes on the compensation of our Named Executive Officers, which is expected to be held at the 2026 annual meeting of stockholders.

In early 2021, our board of directors and management team led a dedicated effort to engage with our largest stockholders to discuss topics related to our strategy, board of directors composition, corporate governance, executive compensation, and environmental and social practices. The compensation committee chair and the audit committee chair participated in select meetings and engaged directly with stockholders.

Overall, the feedback we heard from stockholders was supportive of our executive compensation practices, and they did not request any significant changes to our ongoing compensation program. An overview of the insights we gathered in our discussions can be found under the heading “Stockholder Engagement” above. Specific to our executive compensation program, topics included:

49 
50 2023 Proxy Statement graphic

TABLE OF CONTENTS

The CEO Performance Award, including our board of directors’ goals for the award in the context of our strategy and executive compensation program.
Stockholders expressed support for the structure and timing of the CEO Performance Award, noting our strong 2020 performance, the rigorous performance targets, and the highly competitive landscape for talented chief executive officers.
Our decision to introduce PSUs into our long-term incentive compensation program beginning in 2021.
This change was well received by stockholders, who encouraged us to provide relevant disclosure in future proxy statements.

Executive Compensation Program Changes for 2021

To incent long-term value creation and strong financial performance, to further align the interests of our Named Executive Officers with those of our stockholders, and to encourage retention, in February 2021, the compensation committee introduced PSUs into our ongoing long-term incentive compensation program. Ms. Brown and Messrs. McCombs and Gilpin received PSU grants in the following amounts:

Named Executive OfficerTarget Number of PSUsMaximum Number of PSUs
Hayden Brown41,00082,001
Jeff McCombs5,88711,774
Eric Gilpin2,1024,205

The number of PSUs that will become subject to each award, which we refer to as the Earned PSUs, will be earned based on achievement of revenue targets in respect of our fiscal year ending December 31, 2021, which we refer to as the Performance Period. All Earned PSUs will then be subject to an additional time-based vesting requirement, such that the Earned PSUs will only be settled to the extent vested in accordance with the time-based vesting requirement. Under the time-based vesting requirement, one-fourth of the Earned PSUs vest approximately one year following the date of grant and thereafter the remaining Earned PSUs will vest on a quarterly basis over the following three-year period. In aggregate, the Performance Period and the time-based vesting requirement require four years of service for the Earned PSUs to vest fully.

In 2021, the target number of PSUs will comprise 50% of the total long-term incentive opportunity issued to Ms. Brown (excluding her CEO Performance Award) and 20% of the total long-term incentive opportunity issued to Messrs. McCombs and Gilpin.

Full details on the PSUs can be found in the section “2021 PSU Awards” below.

Executive Compensation Philosophy and Objectives

Our executive compensation philosophy is to provide a competitive compensation program that attracts and retains talented executives, including our Named Executive Officers, and to motivate and reward them to meet or exceed our short-term and long-term strategic objectives while simultaneously creating sustainable long-term value for our stockholders. We strive to create an executive compensation program that is competitive, rewards achievement of our strategic objectives, and aligns our executives’ interests with those of our stockholders. Consistent with this philosophy, we designed our executive compensation program to achieve the following primary objectives:

50 
Compensation Philosophy and Objectives

Attract,
We aim to attract, motivate, incentivize, and retain employees at the executive level who contribute to our long-term success.success

Provide
We provide competitive compensation packages to our executives.executives
Reward
We reward the achievement of our business objectives.objectives
Effectively
​We effectively align theiremployee interests with those of our stockholders by focusing on long-term incentive compensation in the form of equity awards that correlate with the growth of sustainable long-term value for our stockholders.stockholders

We structure the annual compensation of our Named Executive Officers using three principal elements: annual base salary, annual performance bonus opportunities, and long-term incentive compensation opportunities in the form of equity awards. We design our executive compensation program to balance the goals of attracting, motivating, rewarding, and retaining our Named Executive Officers with the goal of promoting the interests of our stockholders by aligning the interests of our Named Executive Officers and stockholders and linking pay with performance. We therefore seek to ensure that a meaningful portion of our Named Executive Officers’ annual target annual total direct compensation opportunity is “at-risk” and variable in nature.

To date, we have emphasized variable “at-risk” compensation through two separate compensation elements. First, we provide the opportunity to earn short-term incentives, either through participation in our annual Performance Bonus Planperformance bonus plan or, in the case of Mr. Gilpin, a sales compensation plan. The Performance Bonus Planannual performance bonus plan provides payments if our Named Executive Officers produce short-term results that meet or exceed certain pre-established annual financial targets in effect as determined from time to time by us and approved by our board of directors orthe compensation committee in connection with our annual budget.committee. The sales compensation plan for Mr. Gilpin provides payments as described in “Sales Compensation Plan for Mr. Gilpin” Gilpinbelow. In addition, we grant PSU awards and RSU awards to our Named Executive Officers, the value of which depends entirely on both our short-term and long-term financial performance, which influences the value of our common stock, thereby incentivizing themour Named Executive Officers to build sustainable long-term value for the benefit of our stockholders.

Through the use of these variable pay elements, typically a substantial portion of our Named Executive Officers’ annual target total direct compensation varies based on our performance, with the value ultimately received subject to variability above or below target levels commensurate with our actual performance. We believe this compensation program design provides balanced incentives for our Named Executive Officers to meet our business objectives and drive long-term growth. The compensation committee aims to maintain an appropriate pay-for-performance“pay-for-performance” alignment with an emphasis on long-term stockholder value creation.

We have not adopted policies or employedestablished guidelines for allocating compensation between current and long-term compensation, between cash and non-cash compensation, or among different forms of non-cash compensation. As our needs evolve and as circumstances require, we intend to reevaluate our executive compensation philosophy, primary objectives, and program design.
Finally, we use equity incentives as part of our broad-based compensation program to foster a culture of ownership and shared success among our employees. Please see page 49 of our 2022 Impact Report, which
graphic2023 Proxy Statement 51

TABLE OF CONTENTS

is available on our ESG Reports Hub on our website at upwork.com/about/our-impact/reports-hub, for details regarding the distribution of equity incentives and stock ownership across our employee base. The information contained in our 2022 Impact Report is not intended to be incorporated into this Proxy Statement.
Compensation-Setting Process

01 Annual Review
02 Discussion and
Compensation Setting
03 Ongoing Dialogue
The compensation committee conducts an annual evaluation of our executive compensation program and Named Executive Officers’ compensation to determine potential changes for the next fiscal year

Process includes reviewing compensation information for peer companies and broad-based compensation surveys to understand market compensation levels
Our CEO reviews the performance of our other Named Executive Officers based on their performance overall and against business objectives established for them for the prior year, and then shares these evaluations with, and makes recommendations to, the compensation committee

The compensation committee reviews and discusses CEO recommendations and, in consultation with the compensation consultant, sets the compensation opportunity for each Named Executive Officer
Our CEO attends meetings of the board of directors and the compensation committee at which executive compensation matters are addressed, except for discussions involving her own compensation

The compensation consultant attends the meetings of the compensation committee as requested
Role of the Compensation Committee

The compensation committee has the overall responsibility for overseeing our compensation and benefits plans, policies, and practices generally and with respect to our Named Executive Officers.

In carrying out its responsibilities, the compensation committee evaluates our compensation policies and practices for alignment with our executive compensation philosophy, develops compensation-related strategies, makes decisions that it believes further our philosophy and/or align with compensation best practices, and reviews the performance of our Named Executive Officers when making decisions about their compensation.

51 

Each year, the compensation committee conducts an evaluation of our executive compensation program to determine if any changes are appropriate. The compensation committee also conducts an annual review of the compensation arrangements of our Named Executive Officers, typically during the first quarter of the fiscal year. The compensation committee’s authority, duties, and responsibilities are further described in its charter, which is reviewed annually by the compensation committee and revised as warranted. The charter is available onin the “Investor Relations” section of our website, which is located at https://investors.upwork.com, by clicking on “Documents & Charters” in the “Governance” section of the website.

In making its decisions, including with respect to the compensation of our Named Executive Officers, the compensation committee retains a compensation consultant (as described in “Role of Compensation Consultant” below) to provide support in its review and assessment of our executive compensation program.

Setting Target Total Direct Compensation

Typically, during the first quarter of the fiscal year or more frequently as warranted, the compensation committee reviews the annual base salary levels, annual performance bonus opportunities, and long-term incentive compensation opportunities of our Named Executive Officers and all related performance criteria. Adjustments are generally effective at the beginning of the fiscal year or at the time of a promotion.promotion, as the case may be.
52 2023 Proxy Statement graphic

TABLE OF CONTENTS

The compensation committee does not establish a specific target for formulating the target total direct compensation opportunities of our Named Executive Officers. Instead, in consultation with its compensation consultant, Compensia, Inc., which we refer to as Compensia, the compensation committee weighs various considerations, including the following:

our executive compensation program objectives;
our performance against the financial, operational, and strategic objectives established by the compensation committee and our board of directors;
each individual Named Executive Officer’s knowledge, skills, experience, qualifications, tenure, and scope of roles and responsibilities relative to other similarly-situated executives at the companies in our compensation peer group and in selected broad-based compensation surveys;
the prior performance of each individual Named Executive Officer, based on a subjective assessment of his or her contributions to our overall performance, ability to lead his or her business unit or function, and work as part of a team, all of which reflect our core values;
the potential of each individual Named Executive Officer to contribute to our long-term financial, operational, and strategic objectives;
our Chief Executive Officer’s compensation relative to that of our Named Executive Officers, and compensation parity among our Named Executive Officers;
our financial performance relative to our compensation and performance peers;
the compensation practices of the companies in our compensation peer group and in selected broad-based compensation surveys and the positioning of each Named Executive Officer’s compensation in a ranking of peer company compensation levels based on an analysis of competitive market data; and
the recommendations of our Chief Executive Officer with respect to the compensation of our Named Executive Officers (except with respect to her own compensation).

our executive compensation program objectives;
our performance against the financial, operational, and strategic objectives established by the compensation committee and our board of directors;
each individual Named Executive Officer’s knowledge, skills, experience, qualifications, tenure, and scope of roles and responsibilities relative to other similarly situated executives at the companies in our compensation peer group and in selected broad-based compensation surveys;
the prior performance of each individual Named Executive Officer, based on a subjective assessment of his or her contributions to our overall performance, ability to lead his or her business unit or function, and work as part of a team, all of which reflect our core values;
the potential of each individual Named Executive Officer to contribute to our long-term financial, operational, and strategic objectives;
our CEO’s compensation relative to that of our other Named Executive Officers, and compensation parity among our Named Executive Officers;
our financial performance relative to our compensation and performance peers;
the compensation practices of the companies in our compensation peer group and in selected broad-based compensation surveys and the positioning of each Named Executive Officer’s compensation in a ranking of peer company compensation levels based on an analysis of competitive market data; and
the recommendations of our CEO with respect to the compensation of our Named Executive Officers (except with respect to her own compensation).
These factors provide the framework for compensation decision-making and final decisions regarding the compensation opportunity for each Named Executive Officer. No single factor is determinative in setting compensation levels, nor is the impact of any individual factor on the determination of pay levels quantifiable.

52 

The compensation committee does not engage in formal benchmarking against other companies’ compensation programs or practices to establish our compensation levels or make specific compensation decisions with respect to our Named Executive Officers. The compensation committee believes that over-relianceoverreliance on benchmarking can result in compensation that is unrelated to the value actually delivered by our Named Executive Officers because compensation benchmarking does not take into account the specific performance of the Named Executive Officers or our relative size and performance.

Instead, in making its determinations, and in consultation with the compensation consultant, the compensation committee reviews compensation information for a representative group of peer companies to the extent that the executive positions at these companies are considered comparable to our executive officers’ positions and informative of the competitive environment. The compensation committee also reviews broad-based compensation surveys to understand market compensation levels. These principles and processes apply to both cash and equity-based compensation awards granted under our programs.executive compensation program.
Role of Management
In discharging its responsibilities, the compensation committee works with members of our management, including our CEO. Our management assists the compensation committee by providing information on corporate and individual performance and management’s perspective on compensation matters. The compensation committee solicits and reviews our CEO’s proposals with respect to program structures, as
graphic2023 Proxy Statement 53

TABLE OF CONTENTS

well as our CEO’s recommendations for adjustments to annual cash compensation, long-term incentive compensation opportunities, and other compensation-related matters for our Named Executive Officers (except with respect to her own compensation) based on our CEO’s evaluation of their performance for the prior year.
At the beginning of each year, our CEO reviews the performance of our other Named Executive Officers based on their overall performance and performance against business objectives established for them for the prior year and then shares these evaluations with, and makes recommendations to, the compensation committee for each element of compensation as described above. The annual business objectives for each Named Executive Officer are developed through mutual discussion and agreement between our CEO and the Named Executive Officers and are also reviewed with our board of directors.
The compensation committee reviews and discusses our CEO’s recommendations and considers them as one factor in determining and approving our Named Executive Officers’ compensation. Our CEO also attends meetings of the board of directors and the compensation committee at which executive compensation matters are addressed, except for discussions involving her own compensation.
Competitive Positioning
The compensation committee believes that peer group comparisons are useful guides to measure the competitiveness of our executive compensation program and related policies and practices. To assess our executive compensation against the competitive market, the compensation committee reviews and considers the compensation levels and practices of a select group of peer companies.
This compensation peer group consists of technology companies that are similar to us in terms of revenue, market capitalization, and industry focus. The competitive data drawn from this compensation peer group is only one of several factors that the compensation committee considers, however, in making its compensation decisions for our Named Executive Officers.
In February 2022, the compensation committee used the compensation peer group set forth below to analyze the compensation of our then-Named Executive Officers and make its initial compensation decisions for the year. This compensation peer group, which was developed in July 2021 with the assistance of Compensia after conducting a thorough review of our then-compensation peer group, was comprised of publicly traded technology companies against which we compete for executive talent. In evaluating the companies comprising the compensation peer group, Compensia specifically considered and weighed the following primary criteria, among other factors:
Primary Criteria for Peer Group Selection—July 2021
Geography and Public Company Status
Publicly traded companies primarily headquartered in the United States and traded on a major U.S. stock exchange
Industry
Software and internet companies with a focus on online marketplaces
Revenue
Similar revenue to ours–within a range of approximately 0.5x to approximately 2.0x our revenue (based on the then-last four fiscal quarters) of approximately $404 million (approximately $200 million to approximately $810 million)
Market Capitalization
Similar market capitalization to ours–within a range of approximately 0.33x to approximately 3.0x our then 30-day market capitalization of approximately $6.7 billion (approximately $2.2 billion to approximately $20.1 billion)
54 2023 Proxy Statement graphic

TABLE OF CONTENTS

As a result, the compensation committee approved an updated compensation peer group consisting of the following companies:
2022 Peer Group
Alteryx
Chegg
Q2 Holdings
Anaplan
Everbridge
Redfin
AppFolio
Fastly
Revolve Group
Appian
Fiverr International
Shutterstock
Asana
LivePerson
Smartsheet
BlackLine
Magnite
Stamps.com
CarGurus
Paylocity
Seven companies, Benefitfocus, Cars.com, EverQuote, Quotient Technology, The RealReal, TrueCar, and Yext, were removed from our compensation peer group because their market capitalization was no longer within our targeted market capitalization range; two companies, Eventbrite and TechTarget, were removed because their revenue was no longer within our targeted revenue range; and one company, Pluralsight, was removed because it had been acquired. The following 11 companies were added to our peer group on the basis of their similarity to us in size, revenue, market capitalization, and industry sector: Alteryx, Anaplan, Asana, BlackLine, Chegg, Everbridge, Fastly, Paylocity, Q2 Holdings, Revolve Group, and Smartsheet.
Upwork
2022 Peer Group Median
Total Revenue ($ millions)(1)
404
422
Market Capitalization ($ millions)(2)
6,687
6,020
(1)
Total revenue measured as of June 2021 and reflects the most recently reported four fiscal quarters.
(2)
Market capitalization measured based on the average of the 30 trading-day period ended July 13, 2021.
The compensation committee used data drawn from the companies in our compensation peer group, as well as data from a custom data cut of 68 U.S.-based software companies with revenues ranging from approximately $200 million to approximately $810 million and market capitalizations ranging from approximately $2.2 billion to approximately $20.1 billion (including peer company participants) drawn from the Radford Global Technology Survey database, to evaluate the competitive market when determining the total direct compensation packages for our Named Executive Officers, including annual base salary, target annual performance bonus opportunities, and long-term incentive compensation opportunities. All of the compensation peer group companies that participate in the Radford Global Technology survey were included in the custom data cut.
This compensation peer group was used by the compensation committee for most of 2022 as a reference for understanding the competitive market for executive positions in our industry sector.
The compensation committee reviews our compensation peer group at least annually and makes adjustments to its composition if warranted, taking into account changes in both our business and the businesses of the companies in the peer group.
Role of Compensation Consultant
The compensation committee engages an external compensation consultant to assist it by providing information, analysis, market compensation data, and other advice for our executive compensation program and the decisions resulting from its annual executive compensation review. The compensation consultant reports directly to the compensation committee and its chair and serves at the discretion of the compensation committee, which reviews the engagement annually.
In 2022, the compensation committee again engaged Compensia to serve as its compensation consultant to advise on executive compensation matters.
graphic2023 Proxy Statement 55

TABLE OF CONTENTS

During 2022, Compensia attended the meetings of the compensation committee (both with and without management present) as requested and provided various services, which included the following:
consultation with the compensation committee chair and other members between compensation committee meetings;
review, research, and updating of our compensation peer group;
an analysis of competitive market data for our executive positions, including our Named Executive Officer positions, and an evaluation of how the compensation we pay our executives compares both to our performance and to how the companies in our compensation peer group and/or selected broad-based compensation surveys compensate their executives;
review and an analysis of the base salary levels, annual bonus opportunities, and long-term incentive compensation opportunities of our executives, including our Named Executive Officers;
an assessment of the risk profile of our executive compensation program;
an analysis of a competitive market strategy and the development of equity award guidelines for our broad-based employee population;
an executive compensation program overview;
a review of compensation for the audit committee;
an evaluation of compliance with the CEO pay ratio and the new pay versus performance disclosure requirements;
an analysis of competitive market data for the non-employee members of our board of directors and evaluation of how the compensation we pay the non-employee members of our board of directors compares to how the companies in our compensation peer group compensate the non-employee members of their boards of directors;
a review of competitive practices for stock ownership guidelines;
an update on regulatory developments and market trends; and
review of best practices in equity compensation, including strategies to mitigate the equity burn rate and reduce dilution and better utilize equity to execute on Upwork’s equity compensation goals.
The terms of Compensia’s engagement include reporting directly to the compensation committee chair. Compensia also coordinated with our management for data collection and job matching for our executives. In 2022, Compensia did not provide any other services to us.
The compensation committee has evaluated its relationship with Compensia to ensure that it believes that such firm is independent from management. This review process included a review of the services that Compensia provided, the quality of those services, and the fees associated with the services provided during 2022. Based on this review, as well as consideration of the factors affecting independence set forth in Exchange Act Rule 10C-1(b)(4), Rule 5605(d)(3)(D) of the Nasdaq Marketplace Rules, and such other factors as were deemed relevant under the circumstances, the compensation committee evaluated Compensia’s independence and determined that no conflict of interest has arisen as a result of the work performed by Compensia.
56 2023 Proxy Statement graphic

TABLE OF CONTENTS

Compensation Elements
Annual Base Salary

Annual base salary represents the fixed portion of the compensation of our Named Executive Officers and is an important element of compensation intended to attract and retain highly-talentedhighly talented individuals. Generally, we use base salary to provide each Named Executive Officer with a specified level of cash compensation during the year with the expectation that he or she will perform his or her responsibilities to the best of his or her ability and in our best interests.

Generally, we establish the initial base salaries of our Named Executive Officers through arm’s-length negotiation at the time of hire, taking into account the individual’s position, qualifications, experience, prior salary level, competitive market data, and the base salaries of our other executive officers. Thereafter, the compensation committee reviews the base salaries of our Named Executive Officers each year as part of its annual compensation review, with input from our Chief Executive OfficerCEO (except with respect to her own base salary) and Compensia, and makes adjustments as it determines to be reasonable and necessary to reflect the scope of a Named Executive Officer’s performance, individual contributions and responsibilities, position in the case of a promotion, target total direct compensation opportunity, and market conditions.

In December 2019, in connection with her appointment as our President and Chief Executive Officer, the compensation committee, on behalf of our board of directors, entered into an Amended and Restated Offer Letter with Ms. Brown pursuant to which her annual base salary was increased from $462,250 to $480,000, effective January 1, 2020.

In February 2020,2022, the compensation committee reviewed the annual base salaries of our other then-Named Executive Officers after considering a competitive market analysis prepared by Compensia and the recommendations of our Chief Executive Officer,CEO (except with respect to her own base salary), as well as the other factors described in “Compensation-Setting Process—Setting Target Total Direct Compensation” above. Following this review, the compensation committee determined to adjustincreased the annual base salary of Mr. Gilpin to bring his base salary to a level that was comparable to thateach of similarly situated executivesour then-Named Executive Officers, largely in recognition of the highly competitive and challenging marketplace for skilled and to maintain the annual base salary of Mr. Kinion at its 2019 level.

seasoned executive officers.

Our then-Named Executive Officers’ base salaries were as follows:
Named Executive Officer
2021 Base Salary
($)
2022 Base Salary
($)
Percentage Increase
(%)
Hayden Brown
500,000
550,000
10.0
Jeff McCombs
415,000
500,000
20.5
Eric Gilpin
365,000
412,000
12.9
The 2022 Base Salary rates set forth in the table above were determined in February 2020, were as follows:

53 
2022 but retroactively effective January 1, 2022.

Named Executive Officer2019 Base Salary ($)2020 Base Salary ($)(1)Percentage Increase (%)
Brian Kinion364,000364,000
Eric Gilpin300,472335,00011.5

(1)Mr. Gilpin’s annual base salary increase was effective January 1, 2020.

Subsequently, in connection with his appointment as our Chief Financial Officer in July 2020, our board of directors approved an initial annual base salary for Mr. McCombs of $400,000.

The base salaries paid to our Named Executive Officers during 20202022 are set forth in the “20202022 Summary Compensation Table” below.

Annual Performance Bonus

We use an annual performance bonus plan to motivate our employees, including our Named Executive Officers (other than Mr. Gilpin, our Senior Vice President,Chief Sales Officer, who participates in a separate sales compensation plan)plan described in “Sales Compensation Plan for Mr. Gilpin” below), to achieve our annual business goals as reflected in our annual operating plan. Typically, our board of directors or the compensation committee approves our annual bonus plan, including the performance criteria, at the beginning of the year. However, with the onset of the COVID-19 pandemic induring the first quarter of 2020, following extensive discussions with our Chief Executive Officer and after consulting with Compensia, the compensation committee determined that it was in the best interests of our company and our stockholders to reassess the structure of the proposed annual bonus plan for 2020 once we had a better understanding of how the pandemic was likely to affect our business. While the compensation committee approved target annual bonus opportunities for the members of our leadership team, including our Named Executive Officers, inyear. In February 2020, it took no further action on the bonus plan at that time. At its April 2020 meeting, the compensation committee reviewed with our senior management the uncertain impact of the COVID-19 pandemic on our financial performance and, after consulting with Compensia, determined that it continued to be in the best interests of our company and our stockholders to defer any action on the bonus plan until such time as we had more clarity on such impact.

Subsequently, in July 2020, following a presentation by our Chief Executive Officer describing the effects of the COVID-19 pandemic on our business and the proposed terms for our performance bonus plan for 2020,2022, the compensation committee approved the 20202022 performance criteria, bonus pool, and other terms under our annual performance bonus plan, the Upwork Inc. Performance Bonus Plan, which we refer to as the 20202022 Performance Bonus Plan, to provide annual bonus awards for our employees, including certain of our Named Executive Officers.Officers, and set the target annual bonus opportunities for the members of our leadership team, including our Named Executive Officers, who were participants in the 2022 Performance Bonus Plan.

graphic2023 Proxy Statement 57

TABLE OF CONTENTS

The compensation committee served as the administrator of the 20202022 Performance Bonus Plan. Our board of directors and the compensation committee have the authority to amend or terminate the plan at any time and for any reason, provided that any amendment, suspension, or termination of the plan will not, without a participant’s consent, alter or impair any rights or obligations under any earned award of such participant.

Target Annual Bonus Opportunities

Bonus opportunities under the 2020 Performance Bonus Plan were set at a specific percentage of each participant’s annual base salary.

Named Executive OfficerTarget Bonus Opportunity as % of Salary
Hayden Brown60%
Brian Kinion40%
Jeff McCombs60%

54 

Ms. Brown’s target annual bonus opportunity was set by the compensation committee at 60% of her annual base salary as part of the arm’s length negotiations of her compensation arrangements upon her appointment as our President and Chief Executive Officer effective January 1, 2020, after considering the competitive market for chief executive officers at the companies in our compensation peer group. As noted above, inIn February 2020,2022, the compensation committee reviewed the target annual bonus opportunityopportunities of Mr. Kinion, our other then-NamedNamed Executive OfficerOfficers who was a participantwere participants in our 2020the 2022 Performance Bonus Plan. After taking into considerationPlan after considering a competitive market analysis prepared by Compensia and the recommendations of our Chief Executive Officer,CEO (except with respect to her own target annual bonus opportunity), as well as the other factors described in “Compensation-Setting Process—Setting Target Total Direct Compensationabove,above. Following this review, the compensation committee determined to maintain the percentage target annual bonus opportunities of our Named Executive Officers at their 2021 levels. Recognizing that the combination of maintaining Named Executive Officer 2021 target annual bonus opportunity percentages and increasing base salaries positioned Named Executive Officer target total cash compensation opportunities at levels that were in the top quartile of Mr. Kinion at 40% of his annual base salary.

As previously described, in connection with his appointment as our Chief Financial Officer in July 2020, our board of directors approved athe competitive marketplace, the compensation committee determined that this result was appropriate given the highly competitive and challenging marketplace for skilled and seasoned executive officers.

Our Named Executive Officers’ target annual bonus opportunity foropportunities (other than Mr. McCombs equal to 60% of hisGilpin), as determined in February 2022, were as follows:
Named Executive Officer
2022 Target Annual Bonus Opportunity
(as a percentage of base salary)
2022 Target Annual Bonus Opportunity ($)
Hayden Brown
100%
550,000
Jeff McCombs
80%
400,000
These target annual base salary.

bonus opportunities were effective January 1, 2022.

Corporate Performance Criteria

In July 2020,February 2022, the compensation committee selected revenueCompensation Program Revenue as the performance measure for the 20202022 Performance Bonus Plan. For this purpose, “revenue”“Compensation Program Revenue” meant the sum of (i) our revenue“managed services revenue” for 2020the fiscal year ending December 31, 2022, which we refer to as the Performance Period, less the “costs of talent services to deliver managed services” for the Performance Period plus (ii) “marketplace revenue” for the Performance Period, in each case as reported toin our board of directors followingAnnual Report on Form 10-K filed with the SEC for our fiscal year 2020 under the then-applicable Financial Accounting Standards Board (FASB) Accounting Standards Codification guidance, except as otherwise determined by our board of directors or the compensation committee.ending December 31, 2022. The computation of the revenueCompensation Program Revenue target achievement was to be determined in our sole discretion, as approved by our board of directors or the compensation committee.

We used Compensation Program Revenue as the performance measure for the 2022 Performance Bonus Plan to account for clients that may switch mid-year to utilizing our managed services offering so that the achievement of bonus opportunities under our bonus plan are not impacted by the differing GAAP reporting standards for our marketplace offering, which are reported on a “net” basis under GAAP, and our managed services offering, which are reported on a “gross” basis under GAAP. As a result, participants are not able to achieve performance levels under the 2022 Performance Bonus Plan solely as a result of a client changing from our marketplace offering to managed services offerings mid-year.

Compensation Program Revenue is not a financial measure prepared in accordance with generally accepted accounting principles, which we refer to as GAAP. For more information on how we compute this non-GAAP financial measure and a reconciliation to the most directly comparable financial measure prepared in accordance with GAAP, please refer to “Appendix B: Reconciliation of Non-GAAP Financial Measures” in this Proxy Statement.
The compensation committee consistently reviews an array of potential performance measures to determine the appropriate metrics to drive and evaluate the strategic success of our business. The compensation committee selected revenueCompensation Program Revenue as the sole performance measure for the 20202022 Performance Bonus Plan because, in its view, it was most consistent with our near-term objective of driving
58 2023 Proxy Statement graphic

TABLE OF CONTENTS

revenue growth. In the prior year,2021, we used GSV and adjusted EBITDArevenue as additionalthe sole performance measures inmeasure for our bonus plan. The compensation committee determined not to include these metrics for 2020. Given thatplan because revenue growth was the primary focus of our 20202021 annual operating plan,plan. Similarly, the compensation committee believed that our revenueCompensation Program Revenue performance alone would be the best indicator of our successful execution of our business plan in the volatile environment created by the COVID-19 pandemic.2022. For purposes of the 20202022 Performance Bonus Plan, the compensation committee set the revenuefollowing performance levels for our Compensation Program Revenue performance for 2022:
If our Compensation Program Revenue for 2022 was at or below $538,600,000, there would be no payout under the 2022 Performance Bonus Plan;
If our Compensation Program Revenue for 2022 equaled $588,600,000, our eligible Named Executive Officers would receive a bonus payout equal to 100% of their target annual bonus opportunity under the 2022 Performance Bonus Plan;
If our Compensation Program Revenue for 2022 equaled or exceeded $638,600,000, our eligible Named Executive Officers would receive a bonus payout equal to 200% of their target annual bonus opportunity under the 2022 Performance Bonus Plan; and
Between the threshold Compensation Program Revenue performance level of $538,600,000 and the maximum performance level of $638,600,000, bonus payouts for our Named Executive Officers under the 2022 Performance Bonus Plan would be determined on a straight-line basis.
The target level for Compensation Program Revenue under the fiscal year at $360.0 million. This target level2022 Performance Bonus Plan was greater than the revenueCompensation Program Revenue earned for the prior fiscal year and represented an aggressive level of performance that the compensation committee believed our management team could achieve with diligent effort in the then-existing business environment.

Further, the threshold performance level for the 2022 Performance Bonus Plan represented approximately a 14% year-over-year Compensation Program Revenue growth figure, which the compensation committee determined was appropriate for there to be any payout under the 2022 Performance Bonus Plan.

In the event of an acquisition the bonus payout percentage was to be determined using the most recent Compensation Program Revenue forecast for 2022, as approved by our board of directors, and the amount of the bonus was to be pro-rated based on the amount of base salary actually paid to a particular participant between the first date of fiscal year 2022 and the date of the acquisition.
Annual Bonus Plan Formula

The following formula was used to calculate the annual bonuses paid to participants under the 20202022 Performance Bonus Plan:

Bonus Payment
 2020
=
2022 Base Salary
 2020
×
2022 Target

Annual Bonus

Opportunity
 
×
Revenue

Achievement

Percentage

55 

For purposes of the 20202022 Performance Bonus Plan:

“2022 Base Salary” meant the amount of base salary actually earned and paid to the participant during 2022, excluding (i) bonuses, commissions, overtime pay, or the value of any equity securities, or any employee benefits or other compensation paid to the participant (for example, the Section 401(k) plan employer match) and (ii) any compensation paid to a participant in respect of inactive employment by our company (for example, a leave of absence); and
“Revenue Achievement Percentage” meant the achievement of our Compensation Program Revenue target for 2022 expressed as a percentage calculated by measuring our 2022 Compensation Program Revenue on a straight-line basis between the threshold performance level of $538,600,000, where the Revenue Achievement Percentage would be zero, and the maximum performance level of $638,600,000, where the Revenue Achievement Percentage would be 200%; provided, however, that in no event was the Revenue Achievement Percentage to be greater than 200% or less than zero.
“2020 Base Salary” meant the amount of base salary actually earned and paid to the participant during 2020, excluding (i) bonuses, commissions, overtime pay, or the value of any equity securities, or any employee benefits or other compensation paid to the participant (for example, the Section 401(k) plan employer match) and (ii) any compensation paid to a participant in respect of inactive employment by our company (for example, a leave of absence); and
“Revenue Achievement Percentage” meant the achievement of our revenue target for 2020 expressed as a percentage calculated by dividing (i) the difference between our 2020 revenue, minus $310,000,000 by (ii) $50,000,000; provided, however, that in no event was the Revenue Achievement Percentage to be less than zero.
graphic2023 Proxy Statement 59

TABLE OF CONTENTS

Annual Bonus Payments

In February 2021,2023, the compensation committee approved annual bonus awards to the participants in the 20202022 Performance Bonus Plan, including our incumbent Namedthen-Named Executive Officers (other than Mr. Gilpin). Based on the 20202022 performance criteria established by the compensation committee in July 2020,February 2022, the compensation committee determined we achieved revenueCompensation Program Revenue of $373.6$580.6 million, which resultedwas adversely affected by Russia’s invasion of Ukraine and our resulting decision to cease operations in Russia and Belarus early in the year, contributing to a Revenue Achievement Percentage of 127%84%. While this impact to our Compensation Program Revenue was significant and outside of management’s control, the compensation committee determined not to adjust the Compensation Program Revenue performance criteria under the 2022 Performance Bonus Plan or otherwise adjust the payments under the 2022 Performance Bonus Plan. Based on this Revenue Achievement Percentage, the following bonuses werebonus was payable to Ms. Brown, who was our incumbentonly Named Executive OfficersOfficer who were participantswas a participant in the 20202022 Performance Bonus Plan:

Named Executive OfficerTarget Annual Bonus
(as a percentage of base
salary)
Target Annual
Bonus ($)
Earned Annual Bonus
Award ($)
Earned Annual Bonus Award
(as a percentage of Target Annual Bonus)
Hayden Brown60%288,000365,760127%
Jeff McCombs60%99,000(1) 125,730(1) 127%

(1)Mr. McCombs’s annual bonus award was pro-rated due to base salary payments only being earned during his partial year of employment.

Plan at the time the annual bonus awards were paid. Mr. Gilpin was not a participant in the 2022 Performance Bonus Plan as he participates in a separate sales compensation plan, which is described below, and Mr. McCombs was not eligible to receive an annual bonus award because his final day as our Chief Financial Officer was December 31, 2022, which was prior to the date on which the annual bonus awards were paid.

Named Executive
Officer
Target Annual Bonus (as a percentage of base salary)
Target Annual
Bonus ($)
Earned Annual
Bonus Award ($)
Earned Annual Bonus Award (as a percentage of base salary)
Hayden Brown
100%
550,000
462,000
84%
Sales Compensation Plan for Mr. Gilpin

As our Senior Vice President,Chief Sales Officer, Mr. Gilpin’s annual cash incentive for 20202022 was based on his ability to manage our sales organization to (i) achieve our annual enterprise revenue quota and reward him for growing our enterprise accounts for the year and (ii) achieve our annual enterprise sales quota and reward him for our sales team’s enterprise bookings efforts for the year. Each of these performance incentives was weighted 50% for purposes of Mr. Gilpin’s 2022 annual cash incentive. In 2020,2022, Mr. Gilpin was eligible to earn anGilpin’s target annual cash incentive payment of up to $335,000,opportunity was $412,000, which iswas equal to 100% of his 20202022 annual base salary.

This incentive payment was to be calculated and paid quarterly based on our actual enterprise revenue attainment as measured against the applicable quarterly revenue quota for our sales organization.
Mr. Gilpin’s sales compensation plan also included an additional payment if our total enterprise revenue for the year exceeded our annual enterprise revenue quota.
To be eligible for any payment under his annual cash incentive, Mr. Gilpin had to be employed on the last calendar day of the month for which the cash incentive payment was calculated.

In addition, each performance incentive included an additional multiplier if either enterprise revenue or enterprise bookings for the year exceeded his annual quota.

These incentive payments were to be calculated and paid quarterly based on our actual annual enterprise revenue attainment and our actual annual enterprise bookings attainment as measured against the applicable quarterly enterprise revenue and enterprise bookings quotas, respectively, for our sales organization.
Mr. Gilpin’s quarterly payment was capped at 120% of his target incentive payments in the first through third quarters, with no cap on his payments for the fourth quarter.
Mr. Gilpin’s sales compensation plan also included additional payments if our total annual enterprise revenue for the year and total annual enterprise bookings for the year exceeded our annual enterprise revenue and annual enterprise bookings quotas, respectively.
To be eligible for any payment under his annual cash incentive, Mr. Gilpin had to be employed on the last calendar day of the month for which the cash incentive payment was calculated.
We are not disclosing the target level for our annual enterprise revenue quota and annual enterprise bookings quota because we believe to do so would be competitively harmful, as it would give our competitors valuable insight into our strategic and financial planning processes. However, the target performance level for each performance incentive was increased from the target performance level from the prior year, was greater than our actual performance in the prior year, and represented an aggressive level of performance that we believed Mr. Gilpin and our sales organization could achieve with diligent effort.

56 
60 2023 Proxy Statement graphic

TABLE OF CONTENTS

Mr. Gilpin’s

For purposes of his annual cash incentive, payment wasMr. Gilpin’s payments were calculated based on the total revenue attributable to ourhis enterprise accounts compared to the applicable quarterlyyear-to-date quota and the total enterprise bookings compared to the applicable year-to-date quota. For this purpose, achievement of the quota for theeach quarterly measurement period (ending March 31, June 30, September 30, and December 31, 2022, respectively) meant the enterprise revenue or enterprise bookings actually attributable to the period calculated as a percentage of the quota for the period. The paymentMr. Gilpin’s year-to-date total quota attainment was required to be determined on a linear basis of this cumulative target, with no cap on the percentage of the quarterly target that couldgreater than 50% in order to be paideligible for a given period.payment. For example, if the enterprise revenue quota for the period was $1,000 and we achieved enterprise revenue for the period of $610, Mr. Gilpin would be considered to have achieved 61% of his quota.

The same formula was applicable to his annual enterprise bookings quota.

In addition, in the event that the sales organization exceeded our annual enterprise revenue quota or annual enterprise bookings quota, as the case may be, in addition to his quarterly cash incentive payment, Mr. Gilpin was eligible to receive an additional payment equal to 3% of each dollar generatedten times (10x) attainment over the quota for the applicable annual enterprise revenue or enterprise bookings quota, as the case may be, for each performance incentive, which we refer to as the Accelerated Payment. There was no cap on the Accelerated Payment which(which was payable after the end of the year) in addition to the quarterly cash incentive payment.

payments. Further, in the event that the sales organization attained between 50% and 100% of our annual enterprise revenue quota or annual enterprise bookings quota, as the case may be, Mr. Gilpin’s payment was subject to a decelerator equal to two times (2x) of each dollar not generated toward the applicable annual enterprise revenue or enterprise bookings quota, as the case may be.

In 2020,2022, Mr. Gilpin earned an annual cash incentive payment under his sales compensation plan in the aggregate amount of $306,202,$269,568, based on our actual total enterprise revenue performance and our actual enterprise bookings performance as measured against our enterprise revenue and enterprise bookings quotas for 2020.2022. Mr. Gilpin received no Accelerated Payments for 2020.

Gilpin’s annual cash incentive payment equaled approximately 65% of his 2022 target annual cash incentive opportunity.

The annual bonuses and sales compensation awarded to our Named Executive Officers for 20202022 are set forth in the “20202022 Summary Compensation Table” below.

Long-Term Incentive Compensation

We view long-term incentive compensation in the form of equity awards as a critical element of our executive compensation program. We use equity awards to incentivize and reward our Named Executive Officers for long-term corporate performance based on the value of our common stock and, thereby, to align the interests of our Named Executive Officers with those of our stockholders. The realized value of these equity awards bears a direct relationship to our stock price, and, therefore, these awards are an incentive for our Named Executive Officers to create long-term value for our stockholders. Equity awards also help us retain and reward qualified executives in a competitive market. Typically, we have granted equity awards to our Named Executive Officers as part of the compensation committee’s annual review of our executive compensation program.

For 2020,2022, the compensation committee sought to retain, motivate, and reward our long-term incentive compensation program for all Named Executive Officers consistedfor long-term increases in the value of our common stock and, thereby, to align their interests with those of our stockholders, using both RSU awards with time-based vesting requirements that may be settled for shares of our common stock and PSU awards with performance-based vesting requirements and time-based vesting requirements that, if earned, may be settled for shares of our common stock. We grant RSU awards because they enable us to incentivize and retain our Named Executive Officers using fewer shares of our common stock than would be necessary if we used stock options. In addition,options and because they have value to the potential value of these RSU awards increases with any increaserecipient even in the valueabsence of the underlying shares, RSUstock price appreciation. In 2022, we also granted PSU awards also provide incentives to our Named Executive Officers that are aligned with the intereststo enable them to earn shares of our stockholders. In 2021,common stock based on certain pre-established Compensation Program Revenue targets in respect of our year ended December 31, 2022, as described below underin the headingsection titledCEO Performance Award for Ms. Brown,February 2022 Equity Awards,we issued Ms. Brown the CEO Performance Award and also began granting PSUs to our Named Executive Officers as described below under the heading “2021 PSU Awards.

well as continued service.

To date, the compensation committee has not applied a rigid formula in determining the size and form of the equity awards to be granted to our Named Executive Officers as part of our annual focal review of equity awards.Officers. Instead, in making these decisions, the
graphic2023 Proxy Statement 61

TABLE OF CONTENTS

compensation committee has exercised its judgment as to the amount and form of the awards after consideringawards. The compensation committee considers the retention value of the equity compensation held by the Named Executive Officer, the cash compensation received by the Named Executive Officer, a competitive market analysis prepared by Compensia, the recommendations of our CEO (except with respect to her own equity awards), the amount of equity compensation held by the Named Executive Officer (including the current economic value of his or her unvested equity and the ability of these unvested holdings to satisfy our retention objectives), as well as the other factors described in “Compensation-Setting Process—Setting Target Total Direct Compensation” above. Based upon these factors, the compensation committee has determinedexercised its judgment to determine the size of each award at levels it considered appropriate to create a meaningful opportunity for reward predicated on the creation of long-term stockholder value.

57 

February 2022 Equity Awards

2020 Long-Term Incentive for Ms. Brown

Since Ms. Brown had been granted an RSU award covering 870,322 shares of our common stock on December 12, 2019, in connection with her promotion to President and Chief Executive Officer effective January 1, 2020,

In February 2022, the compensation committee determined not to grant her an additional equity award in February 2020, other than the grant of a fully-vested RSU award covering 7,985 shares of our common stock under our 2019 Performance Bonus Plan.

2020 Long-Term Incentive for Mr. Kinion

Mr. Kinion did not receive an equity award in February 2020, other than the grant of a fully-vested RSU award covering 5,548 shares of our common stock under our 2019 Performance Bonus Plan.

2020 Long-Term Incentive for Mr. Gilpin

In February 2020, the compensation committee granted aapproved long-term incentive compensation opportunityopportunities in the form of a time-based RSU award covering 107,758 shares ofequity awards for our common stockNamed Executive Officers in amounts that it considered to Mr. Gilpin.be consistent with our compensation philosophy and desired market positioning. The compensation committee determined the number of shares of our common stock subject to the RSU award granted to Mr. Gilpin after considering a competitive market analysis prepared by Compensia, the recommendations of our Chief Executive Officer, the amount of equity compensation previously awarded to Mr. Gilpin (including the current economic value of his unvested equity awards and the ability of these unvested holdings to satisfy our retention objectives), and the other factors described in “Compensation-Setting Process—Setting Target Total Direct Compensation” above.

The time-based RSU award granted to Mr. Gilpin in February 2020 vests over four years, with 6.25% of the number of shares of our common stock subject to the award vesting on each quarterly anniversary of February 18, 2020, the vesting commencement date, subject to Mr. Gilpin’s remaining continuously employed by us through each applicable vesting date.

2020 Long-Term Incentive for Mr. McCombs

In connection with his appointment as our Chief Financial Officer in July 2020, the compensation committee granted an RSU award covering 274,348 shares of our common stock to Mr. McCombs on August 4, 2020, his initial date of employment. The RSU award will vest and settle as to 75% of the totaltarget number of shares subject to the awardPSU awards granted to our Named Executive Officers (viewed in the aggregate by value) was determined by the compensation committee based on its consideration of the third anniversaryfactors described above. In 2022, the target number of August 18, 2020, which we refer to as the Vesting Commencement Date, and an additional 6.25%PSUs comprised 60% of the total numberlong-term incentive compensation opportunity of shares subjectour Chief Executive Officer and 40% of the total long-term incentive compensation opportunities of Messrs. McCombs and Gilpin.

The equity awards granted to our Named Executive Officers in February 2022 were as follows:
Named Executive
Officer
Restricted Stock
Unit Awards
(number of shares)
Performance Stock
Unit Awards
(target number of units)
Performance Stock
Unit Awards
(maximum number of units)
Hayden Brown
121,765
182,648
365,296
Jeff McCombs
114,155
76,103
152,207
Eric Gilpin
62,785
41,856
83,713
RSU Awards. The RSU awards will vest in equal installments of 1/16th of the award will vest on each quarterly anniversary thereafterof the vesting commencement date, February 18, 2022, subject to the Named Executive Officer’s continuous service with us on each applicable vesting date, as described in the applicable restricted stock unit award agreement, such that the RSU award will vest in full on the fourth anniversary of the Vesting Commencement Date,February 18, 2026. The RSU awards are subject to Mr. McCombs remaining employedacceleration as our Chief Financial Officer on each such vesting date.

In addition, in the event Mr. McCombs’s employment is terminated without “cause” (as defined in Mr. McCombs’s change in control and severance agreement) prior to August 18, 2021, and such termination takes place following a termination of the employment of our Chief Executive Officer, the RSU award will be deemed vested with respect to 6.25% of the total number of shares for each quarterly anniversary of the Vesting Commencement Date that has passed as of the date of such termination of employment without “cause”. Further, in the event Mr. McCombs’s employment is terminated without “cause” or he resigns for “good reason” (as defined in Mr. McCombs’s change in control and severance agreement) after August 18, 2021 and prior to August 18, 2023, the RSU award will be deemed vested with respect to 25% of the total number of shares subject to the award as of August 18, 2021, and an additional 6.25% of the total number of shares subject to the award for each quarterly anniversary of such date that has passed as of the date of such termination of employment without “cause” or resignation for “good reason” (in each case, as defined in Mr. McCombs’s change in control and severance agreement), as applicable. Notwithstanding the foregoing, Mr. McCombs will not be eligible for the benefits described in this paragraph unless he has executed a general release of all claims against us and our affiliates, in the form prescribed by us, and the release has become effective.

58 

Compensation Arrangements with Mr. McCombs. In connection with his appointment as our Chief Financial Officer effective August 4, 2020, we entered into an employment offer letter dated July 10, 2020, with Mr. McCombs, pursuant to which our initial compensation arrangements with Mr. McCombs were as follows:

an annual base salary of $400,000;
eligibility to participate in our annual performance bonus plan with a target annual bonus opportunity equal to 60% of his annual base salary; and
a long-term incentive opportunity as described above.

In connection with his appointment as our Chief Financial Officer effective August 4, 2020, we also entered into a change in control and severance agreement dated August 4, 2020, with Mr. McCombs that provides for certain payments and benefits if his employment is either terminated without cause outside of a “change in control” (as defined in Mr. McCombs’s change in control and severance agreement) or if his employment is terminated without “cause” or by him for “good reason” (in each case, as defined in Mr. McCombs’s change in control and severance agreement) within three months preceding a change in control or within 12 months following a change in control, in each instance subject to certain restrictive covenants and in exchange for a customary release of claims. These payments and benefits and the triggering events providing for such payments and benefits are described in more detail in Potential Payments Uponupon Termination or Change in Control” below.

Mr. McCombs’s offer letter was approved by our board of directors. In establishing his initial compensation arrangements, we took into consideration the requisite experience and skills that a qualified candidate would need to manage a growing business in a dynamic and ever-changing environment, the competitive market for similar positions at other comparable companies based on a review of compensation survey data, and the need to integrate him into the executive compensation structure that we had developed since our initial public offering, balancing both competitive and internal equity considerations. For a summary of the material terms and conditions of Mr. McCombs’s offer letter, see “Offer Letters” below.

CEO Performance Award for Ms. Brown

Our board of directors and the compensation committee determined that Ms. Brown decisively demonstrated outstanding and exceptional capabilities in her first year as President and Chief Executive Officer. Accordingly, the compensation committee granted Ms. Brown an additional incentive commensurate with the level of achievement and ambition she had demonstrated as President and Chief Executive Officer, while also promoting her retention in a highly competitive market for this level of leadership capability.

On January 18, 2021, which we refer to as the Grant Date, the compensation committee granted to Ms. Brown the CEO Performance Award, exercisable for up to 1,500,000 shares of our common stock at a per share exercise price of $38.80, subject to the achievement of certain pre-established per share stock price targets, which we refer to as the Performance Vesting Requirement, and a four-year service-based vesting requirement, which we refer to as the Service Vesting Requirement. For the CEO Performance Award to be exercisable for any shares of our common stock, both the Performance Vesting Requirement and the Service Vesting Requirement must be met with respect to such shares, and the majority of the award’s value will be earned only if the most rigorous goals are achieved.

After significant discussion among its members and review of data prepared by the compensation committee’s independent compensation consultant, the compensation committee determined that the CEO Performance Award will serve to strengthen the alignment of Ms. Brown’s interests with those of our stockholders by creating a strong and direct link between her long-term incentive compensation opportunities and our long-term performance.

59 

Performance Vesting Requirement

The shares of our common stock subject to the CEO Performance Award are eligible to vest with respect to the Performance Vesting Requirement to the extent the volume-weighted average per share price of our common stock measured over any consecutive 90-day period, with the last 90-day measurement period ending on the 90th day following the fifth anniversary of the Grant Date, which we refer to as the Final Measurement Date, equals or exceeds an applicable per share stock price target as set forth in the following table:

Per Share Stock PriceNumber of Shares Vested
$60.00100,000
$70.00200,000
$80.00300,000
$90.00400,000
$100.00500,000

The performance levels and targets associated with the award are very rigorous and require exceptional stockholder value creation to vest:

Stock Price Hurdles and Implied Stock Price Appreciation

Except as described below, the CEO Performance Award will expire with respect to any shares of common stock that have not satisfied the Performance Vesting Requirement on or before the earlier of:

the Final Measurement Date;
a “change in control” (as defined in Ms. Brown’s change in control and severance agreement, which we refer to as the CIC Agreement); and
the date on which Ms. Brown is no longer serving as our Chief Executive Officer; provided that in the event Ms. Brown no longer serves as our Chief Executive Officer, the CEO Performance Award will remain outstanding and eligible to vest as necessary to give effect to the terms of the CEO Performance Award.

60 

In the event of a change in control (i) during which Ms. Brown is serving as our Chief Executive Officer, or (ii) within three months following a termination of Ms. Brown’s employment as Chief Executive Officer by us without “cause” or by Ms. Brown for “good reason” (in each case, as defined in the CIC Agreement), then the price per share applicable to the change in control will be applied to determine whether any per share stock price target as set forth in the above table has been achieved, and the number of shares listed directly across from such stock price will vest with respect to the Performance Vesting Requirement. In the event of a termination of Ms. Brown’s employment as our Chief Executive Officer either (x) by us without “cause” or a resignation of Ms. Brown for “good reason”, or (y) due to Ms. Brown’s death or disability, and such termination takes place on a date on which the volume-weighted average per share price of our common stock for a minimum of 45 consecutive days immediately preceding such termination equals or exceeds an applicable per share stock price target as set forth in the above table, then the number of shares listed directly across from such stock price will vest with respect to the Performance Vesting Requirement.

In the event that Ms. Brown’s services with us are terminated in a manner that could not give rise to accelerated vesting in accordance with the terms set forth in this description, any portion of the CEO Performance Award that is then-unvested as of the date of such termination of service will be forfeited.

Service Vesting Requirement

The CEO Performance Award is also subject to a four-year time-based vesting requirement. The shares of our common stock subject to the CEO Performance Award are eligible to vest with respect to the Service Vesting Requirement with respect to 6.25% of each tranche of shares subject to the CEO Performance Award on each quarterly anniversary of the Grant Date (with each number of shares associated with a specific per share stock price target noted in the above table constituting a separate tranche), subject to Ms. Brown’s continuous service to us as our Chief Executive Officer, Executive Chairperson, or any C-level officer position, each of which we refer to as a Designated Position, on each applicable vesting date. With respect to the Service Vesting Requirement, but not the Performance Vesting Requirement, the vesting of the shares of our common stock subject to the CEO Performance Award will accelerate as follows: (a) as set forth in the CIC Agreement (as described in “Post-Employment Compensation” below), and (b) in the event that Ms. Brown is terminated or resigns from a Designated Position due to her death or disability, the CEO Performance Award will accelerate with respect to that number of shares that would have vested in accordance with the Service Vesting Requirement over the 12 months immediately following such termination or resignation, only to the extent that such number of shares have satisfied the Performance Vesting Requirement as of immediately prior to such termination or resignation. Any vesting (including any vesting acceleration) with respect to the Service Vesting Requirement will apply proportionately to each tranche of shares of our common stock.

The equity awards granted to our incumbent Named Executive Officers during 2020 are set forth in the “2020 Summary Compensation Table” and the “2020 Grants of Plan-Based Awards Table” below. The stock option granted to Ms. Brown will appear in the Summary Compensation Table included in our proxy statement for our 2022 annual meeting of stockholders.

2021 PSU Awards

As described above, the compensation committee approved in February 2021 the following grants of PSUs to Ms. Brown and Messrs. McCombs and Gilpin:

Named Executive OfficerTarget Number of PSUsMaximum Number of PSUs
Hayden Brown41,00082,001
Jeff McCombs5,88711,774
Eric Gilpin2,1024,205

61 

In 2021, the target number of PSUs will comprise 50% of the total long-term incentive opportunity issued to Ms. Brown (excluding her CEO Performance Award) and 20% of the total long-term incentive opportunity issued to Messrs. McCombs and Gilpin.

. The PSUsPSU awards have both a performance-based vesting requirement and a time-based vesting requirement. The number of PSUs that could become subject to each award, willwhich we refer to as the Earned PSUs, were to be earned based onsubject to the achievement of revenuecertain pre-established Compensation Program Revenue targets in respect of our fiscal year ending December 31, 2021. Allthe Performance Period. Following the Performance Period, all Earned PSUs will bewere then subject to aan additional time-based vesting requirement, such that the Earned PSUs will onlywould be settled only to the extent vested in accordance with the time-based vesting requirement. requirement described below.

The various performance levels for our 2022 Compensation Program Revenue and the number of PSUs earned at each performance level were as follows:
Performance Level
Compensation Program Revenue During Performance Period
Percentage of PSUs to Become
Earned PSUs
Threshold
$538,600,000 and below
0%
Target
$588,600,000
100%
Maximum
$638,600,000 and above
200%
62 2023 Proxy Statement graphic

TABLE OF CONTENTS

Between Compensation Program Revenues of $538,600,000 and $638,600,000, the number of Earned PSUs were to be determined on a straight-line basis.
For purposes of the PSU awards, “Compensation Program Revenue” meant the sum of (i) our “managed services revenue” for the Performance Period, less the “costs of talent services to deliver managed services” for the Performance Period plus (ii) “marketplace revenue” for the Performance Period, in each case as reported in our Annual Report on Form 10-K filed with the SEC for our fiscal year ending December 31, 2022. This is the same definition of “Compensation Program Revenue” as used to determine bonuses under our 2022 Performance Bonus Plan, as described above. The computation of the Compensation Program Revenue target achievement was to be determined in our sole discretion, as approved by the compensation committee.
Compensation Program Revenue is not a financial measure prepared in accordance with GAAP. For more information on how we compute this non-GAAP financial measure and a reconciliation to the most directly comparable financial measure prepared in accordance with GAAP, please refer to “Appendix B: Reconciliation of Non-GAAP Financial Measures” in this Proxy Statement.
Under the time-based vesting requirement, one-fourth25% of the Earned PSUs vest approximately one year followingon the dateone-year anniversary of grantthe February 18, 2022 vesting commencement date and thereafter an additional 1/16th of the remaining Earned PSUs will vest on aeach quarterly basis overanniversary thereafter, subject to the following three-year period.Named Executive Officer’s continuous service with us on each applicable vesting date. In the aggregate, the Performance Period and the time-based vesting requirement require four years of service for the Earned PSUs to vest fully.

The actual number of Earned PSUs will be determined by our performance against certain revenue targets in respect of our fiscal year ending December 31, 2021. We do not disclose the total revenue targets until after the end of the performance period due to competitive concerns; those targets will be disclosed after the 2021 performance period in our proxy statement for our 2022 annual meeting of stockholders.

As soon as reasonably practicable following the completion of the Performance Period, the compensation committee will determine and certify the revenue attained during the Performance Period and the number of Earned PSUs, the date of

On February 18, 2023, which we refer to as the Certification Date. Ms. BrownDate, the compensation committee determined and Messrs. McCombscertified in writing that we had attained Compensation Program Revenue for 2022 in the amount of $580.6 million (as calculated consistently with the terms of the PSU awards in the manner described above), which was adversely affected by Russia’s invasion of Ukraine and Gilpin mustour resulting decision to cease operations in Russia and Belarus early in the year. Based on such Compensation Program Revenue performance, 84% of the target PSUs were eligible to become Earned PSUs. Each then-Named Executive Officer earned the number of Earned PSUs set forth next to their name in the following table, with 25% of such Earned PSUs vesting and being settled in the number of shares of our common stock set forth next to their name in February 2023:
Named Executive Officer
Earned PSUs
(number of units)
Units Settled for Shares of
Our Common Stock on
February 18, 2023
Hayden Brown
153,424
38,356
Jeff McCombs
Eric Gilpin
35,159
8,790
Each Named Executive Officer was required to be employed byin continuous service with us on the Certification Date in order for thehis or her PSUs to become Earned PSUs. If their service terminatesterminated for any reason prior to the Certification Date, all such PSUs willwould be forfeited.

One-fourth offorfeited, as was the Earnedcase for Mr. McCombs.

With respect to the PSUs will then vest approximately one year followinggranted to Ms. Brown, the date of grant and 6.25% ofacceleration provisions set forth in her Severance Agreement (as defined below) do not apply to the Earned PSUs will vest on each quarterly anniversary thereafter, subject to continuous employment on each vesting date.

InPSUs. However, in the event of a corporate transaction (as defined in the 2018 Plan) during the Performance Period, the numbertermination of Earned PSUs will be determined and certified immediately prior to the closing of such corporate transactionMs. Brown’s employment either by treating our most recent revenue forecast (as delivered and approved by our board of directors) as of the date of the corporate transaction as our revenue for the Performance Period. Furthermore, in the event thatus without “cause” or a corporate transaction occurs following the Performance Period but prior to the Certification Date, the revenue forecast will be determined and certified immediately prior to the closing of such corporate transaction based on then-actual projections of revenue, as determined by the compensation committee. In the event that (i) Ms. Brown is subject to a qualifying termination (as defined in her CIC Agreement) or (ii) eitherresignation of Ms. Brown and Messrs. McCombs or Gilpin are subject to a CIC qualifying termination (as defined in their change in control and severance agreements), in each case,for “good reason,” the time-vestingtime-based vesting requirement of the Earned PSUsdescribed above will accelerate in a manner consistent with the acceleration provisions (andset forth in her Severance Agreement (as described in “Potential Payments upon Termination or Change in Control” below).

With respect to the PSUs granted to Mr. Gilpin, the acceleration provisions set forth in his Severance Agreement do not apply. However, in the event of a termination of Mr. Gilpin’s employment either by us without “cause” or a resignation by Mr. Gilpin for “good reason” within 12 months following or within three months preceding a “change in control” of the company, the time-based vesting requirement described above will accelerate in a manner consistent with the acceleration provisions set forth in his Severance Agreement (as described in “Potential Payments upon Termination or Change in Control” below).
graphic2023 Proxy Statement 63

TABLE OF CONTENTS

August 2022 Equity Awards
Russia’s invasion of Ukraine had a significant impact on our workforce. Upwork has historically engaged independent talent from Ukraine, Russia, and Belarus on our work marketplace to perform services for us. The invasion created an immediate threat to the lives and safety of many of these individuals and their families. The danger, dislocation, and disruption experienced by our colleagues required our senior leaders to take extraordinary steps to serve and support our workforce and deliver business continuity, including assisting and paying for team members to relocate out of the impacted region.
In recognition of their extraordinary leadership in navigating the crisis resulting from Russia’s invasion of Ukraine and its impact on our workforce, in July 2022, at the recommendation of Ms. Brown, the compensation committee approved long-term incentive compensation opportunities in the form of one-time RSU awards with a value of $250,000 each to the members of our leadership team, including Messrs. McCombs and Gilpin (but not Ms. Brown), and granted them effective August 18, 2022. The number of shares of our common stock subject to these RSU awards was determined by dividing $250,000 by the average of the closing sale prices of our common stock as quoted on the Nasdaq Global Market for the 30 calendar days ending on the last trading day immediately preceding August 18, 2022, the date of grant of the RSU awards.
The equity awards granted to our Named Executive Officers on August 18, 2022 were as follows:
Named Executive Officer
Restricted Stock Unit Awards (target dollar value) ($)
Restricted Stock Unit Awards (number of units)
Hayden Brown
Jeff McCombs
250,000
12,171
Eric Gilpin
250,000
12,171
The RSU awards vest in equal installments of 25% of the award on each quarterly anniversary of the vesting commencement date, August 18, 2022, subject to the same conditions)Named Executive Officer’s continuous service with us on each applicable vesting date, as provideddescribed in the applicable restricted stock unit award agreement, such that the RSU award will vest in full on the first anniversary of the vesting commencement date. The RSU awards are subject to acceleration as described in “Potential Payments upon Termination or Change in Control” below.
The unvested portion of the RSU awards are subject to forfeiture upon the recipient’s termination of service with Upwork. Mr. McCombs forfeited 9,129 shares subject to his RSU award upon his separation from Upwork on December 31, 2022.
The equity awards granted to our Named Executive Officers during 2022 are set forth in the “2022 Summary Compensation Table” and the “2022 Grants of Plan-Based Awards Table” below.
Executive Compensation Program Changes for 2023
To incentivize long-term value creation and strong financial performance, to further align the interests of our Named Executive Officers with those of our stockholders, and to promote retention of our Named Executive Officers, the compensation committee determined that the target number of PSUs granted in 2023 to our Named Executive Officers should represent at least half of their respective changetotal target long-term incentive opportunity. As a result, in control and severance agreement.February 2023, the compensation committee increased the percentage allocation of PSUs that comprise Mr. Gilpin’s long-term incentive opportunity. Accordingly, the target number of PSUs granted to Mr. Gilpin in 2023 will comprise 50% of his total target long-term incentive opportunity, increased from 40% in 2022. Ms. Brown’s target number of PSUs granted in 2023 will remain 60% of her total target long-term incentive opportunity.
64 2023 Proxy Statement graphic

TABLE OF CONTENTS

Other Compensation Elements
Health and Welfare Benefits

Our Named Executive Officers are eligible to participate in the same employee benefit plans, and generally on the same terms and conditions, as all other U.S. full-time employees. These benefits include medical, dental, and vision insurance, business travel insurance, an employee assistance program, mental health benefits, health and dependent care flexible spending accounts, basic life insurance, accidental death and dismemberment insurance, short-term and long-term disability insurance, commuter benefits, and reimbursement for mobile phone coverage.

We also sponsor a Section 401(k) retirement plan, which we refer to as the Section 401(k) Plan, that provides eligible employees, including our Named Executive Officers, with an opportunity to save for retirement on a tax-advantaged basis.

U.S. employees who have attained at least 18 years of age are generally eligible to participate in the Section 401(k) Plan as of the first day of the calendar month. Participants may make pre-tax or post-tax contributions to the Section 401(k) Plan, from their eligible earnings upsubject to the statutorily prescribed annual limitlimits on pre-tax contributions under the Internal Revenue Code, which we refer to as the Code. Currently, we match 50% of a participant’s contributions to the Section 401(k) Plan in cash, subject to an annual maximum limit of $5,000 per employee. An employee’s interest in our match of a participant’s contributions is 100% vested after one year of service. An employee’s interest in his or her pre-tax or post-tax deferrals is 100% vested when contributed.

We design and adjust our employee benefits programs to be affordable and competitive in relation to the market as well as compliant with applicable laws and practices.

62 

Perquisites and Other Personal Benefits

Currently, we do not view perquisites or other personal benefits as a significant component of our executive compensation program. Accordingly, we do not provide significant perquisites or other personal benefits to our Named Executive Officers except as generally made available to our employees or in situations where we believe it is appropriate to assist an individual in the performance of his or her duties, to make him or her more efficient and effective, and for recruitment and retention purposes. During 2020,2022, none of our Named Executive Officers received perquisites or other personal benefits that were, in the aggregate, equal to $10,000 or more for any individual.

In the future, we may provide perquisites or other personal benefits in limited circumstances, subject to approval and periodic review by the compensation committee.

Role of Management

In discharging its responsibilities, the compensation committee works with members of our management, including our Chief Executive Officer. Our management assists the compensation committee by providing information on corporate and individual performance and management’s perspective on compensation matters. The compensation committee solicits and reviews our Chief Executive Officer’s proposals with respect to program structures, as well as our Chief Executive Officer’s recommendations for adjustments to annual cash compensation, long-term incentive compensation opportunities, and other compensation-related matters for our Named Executive Officers (except with respect to her own compensation) based on our Chief Executive Officer’s evaluation of their performance for the prior year.

At the beginning of each year, our Chief Executive Officer reviews the performance of our other Named Executive Officers based on their overall performance and performance against business objectives established for him or her for the prior year, and then shares these evaluations with, and makes recommendations to, the compensation committee for each element of compensation as described above. The annual business objectives for each Named Executive Officer are developed through mutual discussion and agreement between our Chief Executive Officer and the Named Executive Officers and are also reviewed with our board of directors.

The compensation committee reviews and discusses our Chief Executive Officer’s recommendations and considers them as one factor in determining and approving our Named Executive Officers’ compensation. Our Chief Executive Officer also attends meetings of the board of directors and the compensation committee at which executive compensation matters are addressed, except for discussions involving her own compensation.

Role of Compensation Consultant

The compensation committee engages an external compensation consultant to assist it by providing information, analysis, market compensation data, and other advice for our executive compensation program and the decisions resulting from its annual executive compensation review. The compensation consultant reports directly to the compensation committee and its chair, and serves at the discretion of the compensation committee, which reviews the engagement annually.

63 

In 2020, the compensation committee again engaged Compensia to serve as its compensation consultant to advise on executive compensation matters.

During 2020, Compensia attended the meetings of the compensation committee (both with and without management present) as requested and provided various services, which included the following:

consultation with the compensation committee chair and other members between compensation committee meetings;
review, research, and updating of our compensation peer group;
an analysis of competitive market data for our executive positions, including our Named Executive Officer positions, and an evaluation of how the compensation we pay our executives compares both to our performance and to how the companies in our compensation peer group and/or selected broad-based compensation surveys compensate their executives;
review and an analysis of the base salary levels, annual bonus opportunities, and long-term incentive compensation opportunities of our executives, including our Named Executive Officers;
an analysis of competitive market data based on compensation arrangements at various technology companies and the broader technology sector for the Chief Product & Experience Officer position;
an analysis of competitive market data based on compensation peer group data and the broader technology sector for the Chief Financial Officer position;
an analysis of a competitive market strategy and the development of equity award guidelines for our broad-based employee population;
review of our executive compensation philosophy and the review and analysis of broad-based compensation guiding principles;
an analysis of competitive market data for the non-employee members of our board of directors and evaluation of how the compensation we pay the non-employee members of our board of directors compares to how the companies in our compensation peer group compensate the non-employee members of their boards of directors;
review of market equity compensation practices, including burn rate and overhang;
advice on the Compensation Discussion and Analysis section of our proxy statement for our 2020 Annual Meeting;
an analysis of various performance-based equity award designs for our executives;
advice on executive compensation trends within our industry, and an update on corporate governance and regulatory issues and developments; and
support on other ad hoc matters throughout the year.

The terms of Compensia’s engagement include reporting directly to the compensation committee chair. Compensia also coordinated with our management for data collection and job matching for our executives. In 2020, Compensia did not provide any other services to us.

64 

The compensation committee has evaluated its relationship with Compensia to ensure that it believes that such firm is independent from management. This review process included a review of the services that Compensia provided, the quality of those services, and the fees associated with the services provided during 2020. Based on this review, as well as consideration of the factors affecting independence set forth in Exchange Act Rule 10C-1(b)(4), Rule 5605(d)(3)(D) of the Nasdaq Marketplace Rules, and such other factors as were deemed relevant under the circumstances, the compensation committee evaluated Compensia’s independence and determined that no conflict of interest has arisen as a result of the work performed by Compensia.

Competitive Positioning

The compensation committee believes that peer group comparisons are useful guides to measure the competitiveness of our executive compensation program and related policies and practices. To assess our executive compensation against the competitive market, the compensation committee reviews and considers the compensation levels and practices of a select group of peer companies.

This compensation peer group consists of technology companies that are similar to us in terms of revenue, market capitalization, and industry focus. The competitive data drawn from this compensation peer group is only one of several factors that the compensation committee considers, however, in making its compensation decisions for our Named Executive Officers.

In February 2020, the compensation committee used the below compensation peer group to analyze the compensation of our then-Named Executive Officers and make its initial compensation decisions for the year. This compensation peer group, which was developed in July 2019 with the assistance of Compensia after conducting a thorough review of our then-compensation peer group, was comprised of publicly-traded technology companies against which we compete for executive talent. In evaluating the companies comprising the compensation peer group, Compensia specifically considered and weighed the following primary criteria, among other factors:

publicly-traded companies headquartered in the United States and traded on a major U.S. stock exchange;
companies in the broad technology industry with a focus on online marketplaces and software;
similar revenue to ours – within a range of ~0.5x to ~2.0x our revenue (based on the then-last four fiscal quarters) of approximately $263 million (approximately $132 million to approximately $526 million); and
similar market capitalization to ours – within a range of ~0.2x to ~5.0x our then market capitalization of approximately $1.76 billion (approximately $352 million to approximately $8.8 billion).

As a result, the compensation committee approved an updated compensation peer group consisting of the following companies:

AppFolioEtsyShutterstock
AppianLivePersonStamps.com
BenefitfocusPluralsightTechTarget
Care.comQuotient TechnologyTrueCar
CarGurusRedfinYext
Cars.com

65 

 UpworkPeer Group Median
Total Revenue ($ millions) (1) $263$311
Market Capitalization ($ millions) (2) $1,759$1,511

(1)Total revenue measured as of June 2019 and reflects the most recently reported four quarters.
(2)Market capitalization measured based on the average of the 30 trading-day period ended June 12, 2019.

The compensation committee used data drawn from the companies in our compensation peer group, as well as data from a customized data search conducted from the Radford Global Technology Survey database, to evaluate the competitive market when determining the total direct compensation packages for our Named Executive Officers, including annual base salary, target annual bonus opportunities, and long-term incentive compensation opportunities.

The compensation committee reviews our compensation peer group at least annually and makes adjustments to its composition if warranted, taking into account changes in both our business and the businesses of the companies in the peer group.

Employment Arrangements

We entered into written employment offer letters with each of our Named Executive Officers when they joined us, which employment offer letters were amended and restated in May 2018, in the case of Ms. Brown and Messrs. Kinion andMr. Gilpin. Subsequently, Ms. Brown executed an addendum to her amended and restated employment offer letter to reflect her promotion to Chief Marketing &and Product Officer effective April 1, 2019, and thereafter entered into an amended and restated offer letter dated December 8, 2019, to reflect the terms of her employment as our President and Chief Executive Officer effective January 1, 2020. Mr. McCombs entered into a written employment offer letter in July 2020 prior to joining us in August 2020. Collectively, these amended and restated offer letters and Mr. McCombs’s employment offer letter are referred to in this section as the Offer Letters. We believe that these arrangements were necessary to secure the continued service of these individuals in a highly competitive job market.

Each of these Offer Letters provides for “at will” employment (meaning that either we or the Named Executive Officer may terminate the employment relationship at any time with or without cause and with or without notice) and generally sets forth the Named Executive Officer’s then-current annual base salary, eligibility for participation in our annual performance bonus plan, and eligibility to participate in our employee benefit plans, including our health insurance plan and disability insurance plan, as established from time to time. In addition, by executing an Offer Letter, each of Ms. Brown and Messrs. Kinion andMr. Gilpin reaffirmed the terms and conditions of the employee invention assignment and confidentiality agreement and the employee dispute resolution agreement that heshe or shehe had previously entered into with us. Mr. McCombs also entered into an employee invention assignment and confidentiality agreement and an employee dispute resolution agreement with us when he accepted his employment offer letter.Offer Letter.
graphic2023 Proxy Statement 65

TABLE OF CONTENTS

These Offer Letters also provide that each Named Executive Officer will be eligible to enter into a change in control and severance agreement, which we refer to as a Severance Agreement, based on his or her position within our company. These agreements specify the severance payments and benefits that he or she will be eligible to receive in connection with certain terminations of employment from our company. These post-employment compensation arrangements are discussed in “Post-Employment Compensation” below.

For detailed descriptions of the employment arrangements with our Named Executive Officers, see “Potential Payments upon Termination or Change in Control” below.

66 

Post-Employment Compensation

We have entered into change in control and severance agreementsa Severance Agreement with each of our Named Executive Officers, which provideprovides for certain protections in the event of certain involuntary terminations of employment, including a termination of employment in connection with a change in control, of us, in exchange for a general release of claims and compliance with a non-disparagement covenant for a period of 24 months following separation from us. Each change in control and severance agreementSeverance Agreement is in effect for three years, with automatic renewals for new three-year periods unless notice is given by us to the Named Executive Officer three months prior to the date on which the agreement would otherwise renew.

We believe these change in control and severance agreementsSeverance Agreements provide reasonable compensation in the form of severance pay and certain limited benefits to the Named Executive Officer if he or she leaves our employ under certain circumstances to facilitate his or her transition to new employment. Further, we seek to mitigate any potential employer liability and avoid future disputes or litigation by requiring a departing Named Executive Officer to sign a separation and release agreement in a form prescribed by us providing for a general release of all claims as a condition to receiving post-employment compensation payments or benefits. We believe that these agreements help maintain our Named Executive Officers’ continued focus on their assigned duties to maximize stockholder value if there is a potential change in control transaction and mitigate the risk of subsequent disputes or litigation. The terms and conditions of these agreements were approved by our board of directors after an analysis of competitive market data in consultation with Compensia.

Under the change in control and severance agreements,Severance Agreements, all payments and benefits in the event of a change in control of us are payable only if there is a connected loss of employment by a Named Executive Officer (a so-called “double-trigger” arrangement). We use this double-trigger arrangement to protect against the loss of retention value following a change in control of us and to avoid windfalls, both of which could occur if vesting of either equity or cash-based awards accelerated automatically as a result of the transaction.

In the event of a change in control, of us, to the extent Section 280G or 4999 of the Code is applicable to a Named Executive Officer, such individual is entitled to receive either a:

payment of the full amounts specified in his or her agreement to which he or she is entitled; or
payment of such amount that is $1.00 less than the amount that would otherwise trigger the excise tax imposed by Section 4999, depending on which results in the Named Executive Officer receiving a higher amount after taking into account all federal, state, local, and foreign income, employment, and other taxes and the excise tax imposed by Section 4999.

payment of the full amounts specified in his or her agreement to which he or she is entitled; or
payment of such amount that is $1.00 less than the amount that would otherwise trigger the excise tax imposed by Section 4999, depending on which results in the Named Executive Officer receiving a higher amount after taking into account all federal, state, local, and foreign income, employment, and other taxes and the excise tax imposed by Section 4999.
We are not obligated to provide excise tax payments, which we refer to as gross-ups, to any of our executive officers, including our Named Executive Officers.

In connection with her appointment as our President and Chief Executive Officer, in December 2019 Ms. Brown’s CIC Agreement was amended and restated to reflect the terms of her employment as our President and Chief Executive Officer effective January 1, 2020. The CIC Agreement provides for the following payments and benefits if Ms. Brown’s employment is terminated by us without “cause” or by Ms. Brown for “good reason” outside of a “change in control” (as such terms are defined in the CIC Agreement) of us in exchange for a customary release of claims:

67 

a lump sum severance payment equal to 12 months of base salary;
the payment of premiums for continued medical benefits for up to 12 months; and
50% acceleration of any of her then-outstanding and unvested equity awards (other than equity awards that vest, in whole or in part, upon the satisfaction of performance criteria).

If her employment is terminated by us without “cause” or by Ms. Brown for “good reason” within the three months preceding a change in control of us (but after a legally binding and definitive agreement for the potential change in control of us has been executed) or within the 12 months following a change in control of us, then Ms. Brown is eligible to receive the following payments and benefits in exchange for a customary release of claims:

a lump sum severance payment equal to 18 months of base salary;
the payment of premiums for continued medical benefits for up to 18 months;
a lump sum payment equal to Ms. Brown’s then-current target bonus opportunity on a pro-rated basis; and
100% acceleration of any of her then-outstanding and unvested equity awards (other than equity awards that vest, in whole or in part, upon the satisfaction of performance criteria).

This agreement will be in effect for three years, with automatic renewals for new three-year periods unless we give notice to Ms. Brown at least three months prior to the expiration of the agreement.

We believe that having in place reasonable and competitive post-employment compensation arrangements, including in the event of a qualifying termination in connection with or within specified periods before or after a change in control, are essential to attracting and retaining highly-qualifiedhighly qualified executive officers. The compensation committee does not consider the specific amounts payable under the post-employment compensation arrangements when determining our Named Executive Officers’ compensation. We do believe, however, that these arrangements are necessary to offer competitive compensation packages.

66 2023 Proxy Statement graphic

TABLE OF CONTENTS

Transition and Separation Agreement with Mr. Kinion

McCombs

In connection withSeptember 2022, Mr. McCombs, our former Chief Financial Officer, was notified that he was being terminated from his resignationposition. In order to facilitate a smooth transition of his responsibilities, Mr. McCombs continued service as our Chief Financial Officer effective August 4, 2020,through December 31, 2022, which we refer to as the Separation Date. On September 21, 2022, we entered into a transition and separation agreement with Mr. Kinion settingMcCombs, which we refer to as the McCombs Transition Agreement. The amounts payable thereunder were generally consistent with Mr. McCombs’s offer letter and Severance Agreement that Mr. McCombs executed when he joined Upwork. The McCombs Transition Agreement set forth the terms and conditions of his separationcontinued service to us through the Separation Date as well as his severance compensation and transition from our company. In consideration forcertain releases and covenants that the compensation committee believed were valuable to Upwork. Pursuant to the McCombs Transition Agreement, subject to his execution of aan effective general release and waiver of claims and covenant not to sue, Mr. McCombs became entitled to certain payments and benefits, including (i) a lump sum payment equal to six months of his annual base salary, (ii) vesting of a certain RSU award as described in favorgreater detail below, and (iii) the full amount of us, we agreedinsurance premium payments to provide Mr. Kinioncontinue health benefits, for him and his covered dependents under COBRA, through the earlier of (A) the effective date on which he became covered by a substantially equivalent health insurance plan of a subsequent employer, (B) six months following the Separation Date, and (C) the date he was no longer eligible for COBRA benefits.
As of the date of the McCombs Transition Agreement, and consistent with the following payments and benefits:

a lump sum cash payment equal to six months’ base salary;
reimbursement for any insurance premium payments paid by him to receive coverage under the Consolidated Omnibus Budget Reconciliation Act of 1985, as amended, through no later than April 1, 2021; and
ownership of his company-issued laptop.

In addition,terms of his offer letter, the transition agreement provided thatRSU award granted to Mr. Kinion would remain employed as an advisorMcCombs pursuant to our Chief Executive Officer through October 1, 2020. In consideration for the provision of transition and advisory services until October 1,Restricted Stock Unit Award Agreement dated August 4, 2020, which we refer to as the Initial RSU Award, was deemed vested with respect to 137,174 shares of our common stock. Further, upon execution of the McCombs Transition Agreement and contingent upon his remaining continuously employed with us through November 18, 2022 and delivery of an effective general release and waiver of claims and covenant not to sue executed no earlier than the Separation Date, the Initial RSU Award was deemed vested with respect to an additional 17,146 shares of our common stock. The deemed vesting of the 137,174 shares upon execution of the McCombs Transition Agreement and the additional 17,146 shares following November 18, 2022 were consistent with the terms of Mr. Kinion continuedMcCombs’s offer letter, which provided for such vesting of the Initial RSU Award after one year if Mr. McCombs were to receive his monthly base salary as in effect on August 4, 2020, his outstanding stock options continuedbe terminated without cause or resigned for good reason. Pursuant to vest, and hethe McCombs Transition Agreement, Mr. McCombs was eligible to participate in our employee benefit plans (provided that he was no longernot eligible to receive an annual bonus or any other incentive compensation, including under the terms of our 20202022 Performance Bonus Plan).

68 
Plan. The foregoing description of the McCombs Transition Agreement is qualified in its entirety by reference to the full text of the McCombs Transition Agreement, which is filed as an exhibit to our Quarterly Report on Form 10-Q filed with the SEC for the quarterly period ended September 30, 2022.

For detailed descriptions of the post-employment compensation arrangements with all of our Named Executive Officers, as well as an estimate of the potential payments and benefits payable thereunder, see “Potential Payments upon Termination or Change in Control” below.

Confidentiality, Non-Competition, and Non-Solicitation Agreements

Our Named Executive Officers have each entered into agreements containing confidentiality, non-competition, and non-solicitation covenants. Under these agreements, our Named Executive Officers have agreed to refrain from (i) disclosing our proprietary information in perpetuity, (ii) competing with us or soliciting our clients or customers during the period of their employment, and (iii) soliciting our employees or consultants for a period of 12 months following the termination of their employment.

Other Compensation Policies

Stock Ownership Guidelines

Our Stock Ownership Guidelines are designed to encourage our Chief Executive Officer and other executive officers and the members of our board of directors to achieve and maintain a meaningful ownership stake in our company that aligns their interests with those of our stockholders and promotes a long-term perspective in managing our company. In April 2022, we amended our Stock Ownership Guidelines to remove vested stock options from counting toward satisfaction of such guidelines.
graphic2023 Proxy Statement 67

TABLE OF CONTENTS

Our Chief Executive OfficerCEO and other executive officers and the members of our board of directors are expected to accumulate shares of our common stock towardstoward target ownership levels that are based on a multiple of their respective base salary or annual retainer, as the case may be. If any of our executive officers or the members of our board of directors have not satisfied these ownership levels, the Stock Ownership Guidelines require that they retain ownership of shares or shares subject to outstanding stock options according to the retention ratio described below. Currently, the market value of the qualifying shares that each executive officersofficer or membersmember of our board of directors is required to own is as follows:

Individual Subject to Stock Ownership Guidelines
Ownership Level
Chief Executive Officer
5x annual base salary
Other Executive Officers
1x annual base salary
Non-Employee Directors
3x annual general cash retainer for service as a member of our board of directorsdirectors*

*
Excludes any additional cash retainer paid as a result of service as our chairperson, lead independent director, committee chair, or committee member.

The minimum level of ownership is expected to be achieved within five years of the date the applicable individual becomes covered by the Stock Ownership Guidelines, and each such individual is expected to continuously hold a sufficient equitynumber of shares of our common stock to satisfy the ownership level thereafter for the duration the individual is covered by the Stock Ownership Guidelines. Compliance is evaluated by the compensation committee annually, as of fiscal year-end each year. As of December 31, 2020,2022, each of our executive officers, including our Named Executive Officers, and members of our board of directors was either in compliance with the applicable ownership levels required by the Stock Ownership Guidelines or had not been covered by the Stock Ownership Guidelines for five years.

If, following the compliance deadline, an individual covered by the Stock Ownership Guidelines has not satisfied the applicable ownership level called for by the Stock Ownership Guidelines, then he or she must retain ownership of shares based on a retention ratio whichthat is equal to 50% of the net“net profit sharesshares” as follows: each time he or she exercises a stock option, vests in a restricted stock award, or has an RSU award settled for shares of our common stock, he or she is expected to retain 50% of the shares remaining after payment of the option exercise price and taxes owed upon exercise, 50% of the newly-vestednewly vested shares of restricted stock after the payment of applicable taxes, and 50% of the shares received on settlement of the RSU award after the payment of applicable taxes, in each case until the ownership level called for by the Stock Ownership Guidelines is met.

69 

Compensation Recoupment and Forfeiture Policy, or Clawback Policy

In April 2021, the compensation committee approved

We maintain a compensation recoupment and forfeiture policy, or clawback policy,which we refer to as our Clawback Policy, covering all employees who are officers for purposes of Section 16 of the Exchange Act, including current and former Section 16 executive officers, each of whichwhom we refer to as a covered officer,Covered Officer, and which applies to their incentive-based cash compensation and performance-based equity awards.

If incentive-based cash compensation or performance-based equity awards are granted or received by a covered officerCovered Officer that are predicated upon us achieving certain financial results, and if the quarterly or annual financial statements (whether audited or unaudited) are adjusted or restated to correct one or more errors that have a material impact on our financial statements and our board of directors determines that a covered officerCovered Officer engaged in fraud or intentional misconduct that materially contributed to the need for such adjustment or restatement, then we may recoup or require forfeiture of any such amounts or any portion of such amounts that are in excess of any compensation that would have been earned by such covered officerCovered Officer based upon the adjusted or restated financial results in the event of any adjustment or restatement of our financial statements during the three-year period preceding the date on which we determined, or if later first disclosed, that we are or will be preparing an adjustment or restatement.
In determining whether to require recoupment or forfeiture and, if so, the amount of such recoupment or forfeiture, the compensation committee or our board of directors will take into account such factors as it deems appropriate, including, without limitation, the requirements of applicable law, and stock exchange
68 2023 Proxy Statement graphic

TABLE OF CONTENTS

listing requirements, the extent to which the current or former executive officer participated in or otherwise bore responsibility for the facts and circumstances giving rise to the adjustment or restatement, and such other factors as it may deem appropriate under the circumstances. Any recoupment or forfeiture of such amounts will be publicly disclosed to the extent the compensation committee or our board of directors or the compensation committee determines such disclosure is appropriate or otherwise as required by applicable law.

We intend to adopt a general compensation recovery policy (or modify our existing Clawback Policy) covering our short-term and long-term incentive award plans and arrangements in compliance with the listing standards adopted by The Nasdaq Stock Market LLC prior to the date that we are required to do so.
Hedging, Derivative Securities Transactions, Short Selling, and Pledging

Under our Insider Trading Policy, our employees (including our executive officers) and the non-employee members of our board of directors are prohibited from engaging in hedging or monetization transactions involving our securities, such as zero-cost collars and forward sale contracts, and may not contribute our securities to exchange funds that could be interpreted as having the effect of hedging in our securities. Further, our employees (including our executive officers) and the non-employee members of our board of directors are prohibited from engaging in transactions involving options or other derivative securities on our securities, such as puts and calls, whether on an exchange or in any other market and from engaging in short sales of our securities, including short sales “against the box.”

Also, under our Insider Trading Policy, our employees (including our executive officers) and the non-employee members of our board of directors are prohibited from using or pledging our securities as collateral in a margin account or as collateral for a loan unless the pledge has been approved by the designated compliance administrator pursuant to the Insider Trading Policy, which approval is limited to situations where the subject individual has demonstrated the financial capacity to repay the loan without resorting to the pledged securities).

securities.

Exchange Act Rule 10b5-1 Plans

Certain of our executive officers and non-employee directors have adopted written plans, known as Rule 10b5-1 plans, in which they have contracted with a broker to buy or sell shares of our common stock on a periodic basis. Under a Rule 10b5-1 plan, a broker executes trades pursuant to parameters established by the executive officer or non-employee director when entering into the plan, without further direction from them. The executive officer or non-employee director may amend or terminate the plan in specified circumstances.

70 
In 2023, we revised our Insider Trading Policy to ensure that Rule 10b5-1 plans entered into by our executive officers, non-employee directors, and other employees are eligible for an affirmative defense in accordance with new SEC rules regarding Rule 10b5-1 plans.

Tax and Accounting Considerations

The compensation committee takes the applicable tax and accounting requirements into consideration in designing and overseeing our executive compensation program.

Deductibility of Executive Compensation

Section 162(m) of the Code disallows public companies a tax deduction for federal income tax purposes for remuneration in excess of $1 million paid to certain current and former executive officers who are “covered employees.” The Tax Cuts and Jobs Act of 2017 which we refer to as the TCJA, repealed exceptions to the deductibility limit that were previously available for “performance-based compensation,” including equity awards, effective for taxable years after December 31, 2017, subject to certain grandfathering rules. Prior to
While the enactment of the TCJA, Section 162(m) included special transition relief rules pursuant to which remuneration paid according to a compensation plan or agreement that existed prior to a company’s initial public offering and had been publicly disclosed was excluded from the $1 million annual deduction limit. This transition relief applied until the earliest of: (i) the expiration of the plan or agreement; (ii) a material modification of the plan or agreement; (iii) the issuance of all employer stock and other compensation that had been allocated under the plan; or (iv) the first meeting of stockholders at which directors are elected that is after the end of the third calendar year following the calendar year in which our initial public offering occurred.

While our compensation committee considers the deductibility of awards as one factor in determining executive compensation, our compensation committee also looks at other factors in making its decisions, as noted above, and retains the flexibility to award compensation that it determines to be consistent with the goals of our executive compensation program even if the awards are not deductible by us for tax purposes. Further, because of ambiguities and uncertainties as to the application and interpretation of Section 162(m) beyond the control of the compensation committee, no assurances can be given that any compensation paid by us will qualify for the transition relief or be deductible under Section 162(m) even if so intended.

graphic2023 Proxy Statement 69

TABLE OF CONTENTS

Accounting for Stock-Based Compensation

The compensation committee considers accounting implications when designing compensation plans and arrangements for our executive officers and other employees. Chief among these is ASC Topic 718, the standard whichthat governs the accounting treatment of certain stock-based compensation. Among other things, ASC Topic 718 requires us to record a compensation expense in our income statement for all equity awards granted to our executive officers and other employees. This compensation expense is based on the grant date “fair value” of the equity award and, in most cases, will be recognized ratably over the award’s requisite service period (which, generally, will correspond to the award’s vesting schedule). This compensation expense is also reported in the compensation tables below, even though recipients may never realize any value from their equity awards.

Compensation Risk Considerations
The compensation committee, with the assistance of Compensia, periodically reviews our various compensation programs and related policies and practices and believes that the mix and design of the elements of such programs do not encourage our employees, including our executive officers, to take, or reward our employees for taking, inappropriate or excessive risks and accordingly are not reasonably likely to have a material adverse effect on us. In particular, in conducting our review, we consider compensation program attributes that help to mitigate risk, including:

the mix of cash and equity compensation;
the balance of short-term and long-term performance focus;
the oversight of an independent compensation committee;
our Insider Trading Policy, which prohibits the hedging of the economic interest in our securities; and
our annual bonus plans are subject to the achievement of financial performance metrics and offer upside leverage that is within reasonable market norms and provide for uncapped payouts.
the mix of cash and equity compensation;
the balance of short-term and long-term performance focus;
the oversight of an independent compensation committee;
our Insider Trading Policy, which prohibits the hedging of the economic interest in our securities; and
our annual bonus plans being subject to the achievement of financial performance metrics and offering upside leverage that is within reasonable market norms and provide for uncapped payouts.
71 
70 2023 Proxy Statement graphic


REPORT

TABLE OF THE COMPENSATION COMMITTEECONTENTS

Report of the Compensation Committee
This report of the compensation committee is required by the SEC and, in accordance with the SEC’s rules, will not be deemed to be part of or incorporated by reference by any general statement incorporating by reference this proxy statementProxy Statement into any filing under the Securities Act of 1933, as amended, which we refer to as the Securities Act, or under the Exchange Act, except to the extent that we specifically incorporate this information by reference, and will not otherwise be deemed “soliciting material” or “filed” under either the Securities Act or the Exchange Act.

Our compensation committee has reviewed and discussed the Compensation Discussion and Analysis required by Item 402(b) of Regulation S-K with management and based on such review and discussions, the compensation committee recommended to our board of directors that the Compensation Discussion and Analysis be included in this proxy statement.

Proxy Statement.

Submitted by the Compensation Committee


Gregory C. Gretsch, Chair

Elizabeth Nelson


Gary Steele


Anilu Vazquez-Ubarri
72 
graphic2023 Proxy Statement 71


2020

TABLE OF CONTENTS

2022 Summary Compensation Table

The following table provides information concerning compensation awarded to, earned by, or paid to each of our Named Executive Officers for all services rendered in all capacities during 2018, 2019,2020, 2021, and 2020:

Name and Principal
Positions
YearSalary ($)Bonus ($)Stock
Awards ($)(1)
Non-Equity
Incentive Plan
Compensation ($)(2)
All Other
Compensation ($)
Total ($)

Hayden Brown

 

President and Chief Executive Officer

 

2020480,000365,7602,652(3)848,412
2019437,25011,089,217(4)4,425(5)11,530,892
2018365,466(6)105,1347,400(7)478,000

Jeff McCombs

 

Chief Financial Officer(8)

2020165,000100,000(9)4,803,833(10)125,7305,194,563
       

Brian Kinion

 

Former Chief Financial Officer(11)

2020274,379217,829(12)492,208
2019364,00048,04813)14,299(14)426,347
2018345,000142,1405,000(15)492,140

Eric Gilpin

 

Senior Vice President, Sales(16)

 

2020335,000990,296306,2027,489(17)1,638,987
       

2022:
Name and Principal
Positions
Year
Salary
($)
Bonus
($)
Stock
Awards
($)(1)
Option
Awards
($)(1)
Non-Equity
Incentive Plan
Compensation
($)(2)
All Other
Compensation
($)
Total
($)
Hayden Brown
President and Chief Executive Officer
2022
550,000
7,455,075(3)
462,000
7,652(4)
8,474,727
2021
500,000
4,626,440(5)
28,780,212(6)
995,000
7,652(7)
34,909,304
2020
480,000
365,760
2,652(8)
848,412
Jeff McCombs
Former Chief Financial Officer
2022
500,000
4,885,312(9)
284,675(10)
5,669,987
2021
415,000
1,660,779(11)
660,680
9,586(12)
2,746,045
2020
165,000
100,000(13)
4,803,833(14)
125,730
5,194,563
Eric Gilpin
Chief Sales Officer
2022
412,000
2,788,552(15)
269,568
7,871(16)
3,477,991
2021
365,000
593,087(17)
520,739
7,775(18)
1,486,601
2020
335,000
990,296(19)
306,202
7,489(20)
1,638,987
(1)
The amounts reported represent the grant date fair value of the RSUs granted to our Named Executive Officers during 2018, 2019, and 2020, as applicable, as computedcalculated in accordance with ASC 718. See Note 119 to our consolidated financial statements included in our Annual Report on Form 10-K for the year ended December 31, 2020,2022 for a discussion of the relevant assumptions used in calculating these amounts. For PSUs, the amount reported is based on the probable outcome of the applicable performance condition at the time of grant (i.e., based on 100% of performance). The Company estimated the fair value of the CEO Performance Award using a Monte Carlo simulation including dividend yield, risk-free interest rates, and expected volatility. Each of Ms. Brown and Messrs. McCombs and Gilpin was granted RSUs and PSUs in 2022 as described in the section titled “—Compensation Discussion and Analysis—Compensation Elements—Long-Term Incentive Compensation.” In addition, Ms. Brown was granted the CEO Performance Award in 2021. A summary of the CEO Performance Award can be found under the heading “Chief Executive Officer Performance Award” in our 2022 proxy statement filed with the SEC on April 19, 2022. For PSUs granted in February 2022, the maximum performance shares payable and corresponding maximum aggregate value based on the grant date fair value of such awards are (i) 365,296 shares and $8,946,099 for Ms. Brown; (ii) 152,207 shares and $3,727,549 for Mr. McCombs; and (iii) 83,713 shares and $2,050,131 for Mr. Gilpin.
(2)
The amounts reported represent incentive bonuses actually earned pursuant to our 2018, 2019,2020, 2021, and 20202022 performance bonus plans, except for Mr. Gilpin, whose amount reported represents incentive commissions actually earned pursuant to his 2020 Sales Compensation Plan. Payments for 20202022 are described in greater detail in the section titled “CompensationCompensation Discussion and Analysis—Compensation Elements.Elements.
(3)
The amount reported represents (i) $4,473,050 aggregate grant date fair value for PSUs and (ii) $2,982,025 aggregate grant date fair value for RSUs.
(4)
The amount reported represents (i) our matching contribution of $5,000 under our 401(k) Plan and (ii) $2,652 paid to our disability insurance plan.
(5)
The amount reported represents (i) $2,313,220 aggregate grant date fair value for PSUs and (ii) $2,313,220 aggregate grant date fair value for RSUs.
(6)
The amount reported represents the aggregate grant date fair value for the CEO Performance Award.
(7)
The amount reported represents (i) our matching contribution of $5,000 under our 401(k) Plan and (ii) $2,652 paid to our disability insurance plan.
(8)
The amount reported represents payments to our disability insurance plan.
(4)(9)
The amount reported represents (i) $11,020,059$1,863,762 aggregate grant date fair value of an RSU award granted to Ms. Brown in connection with her appointment as our President and Chief Executive Officerfor PSUs and (ii) $69,158$3,021,550 aggregate grant date fair value of an RSU award granted to Ms. Brown pursuant to our 2019 Performance Bonus Plan.for RSUs.
(10)
(5)
The amount reported represents (i) our matching contribution of $647 on Ms. Brown’s behalf$5,000 under our 401(k) Plan, (ii) $2,431$6,115 paid to our disability insurance plan, and (iii) $1,347 in parkingconnection with Mr. McCombs’s termination, a severance payment in the amount of $250,000 and commuting costs paid by us.COBRA reimbursement of $23,560. A summary of the McCombs Transition Agreement can be found under the heading “—Transition and Separation Agreement with Mr. McCombs.”
(6)(11)
The amount reported represents (i) Ms. Brown’s salary of $340,240$332,144 aggregate grant date fair value for PSUs and (ii) a payment of $25,226$1,328,635 aggregate grant date fair value for accrued paid time off.RSUs.
(7)(12)
The amount reported represents (i) our matching contribution of $5,000 on Ms. Brown’s behalf under our 401(k) Plan and (ii) $2,400$4,586 paid to our disability insurance plan.
(8)Mr. McCombs was hired as our Chief Financial Officer in August 2020.
(9)(13)
The amount reported represents a signing bonus paid to Mr. McCombs in connection with his appointment as our Chief Financial Officer.
(10)(14)
The amount reported represents the grant date fair value for an RSU award granted to Mr. McCombs in connection with his appointment as our Chief Financial Officer.
(11)Mr. Kinion served as our Chief Financial Officer until August 2020.
(12)(15)
The amount reported represents (i) a severance payment of $182,000, (ii) COBRA payments of $25,450, (iii) $1,665 in parking costs paid by us, (iv) $3,714 payment to disability insurance plan, and (v) our matching contribution of $5,000 on Mr. Kinion’s behalf under our 401(k) Plan.
(13)The amount reported represents the$1,025,053 aggregate grant date fair value of an RSU award granted to Mr. Kinion pursuant to our 2019 Performance Bonus Plan.for PSUs and (ii) $1,763,499 aggregate grant date fair value for RSUs.
(14)(16)
The amount reported represents (i) our matching contribution of $5,000 on Mr. Kinion’s behalf under our 401(k) Plan and (ii) $4,085$2,871 paid to our disability insurance plan, and (iii) $5,214 in parking and commuting costs paid by us.plan.
(15)(17)
The amount reported represents (i) $118,595 aggregate grant date fair value for PSUs and (ii) $474,492 aggregate grant date fair value for RSUs.
(18)
The amount reported represents (i) our matching contribution of $5,000 under our 401(k) Plan.
(16)Mr. Gilpin was not a Named Executive Officer in 2018 or 2019.Plan and (ii) $2,775 paid to our disability insurance plan.

(17)(19)
The amount reported represents the grant date fair value for an RSU award granted to Mr. Gilpin.
(20)
The amount reported represents (i) our matching contribution of $5,000 under our 401(k) Plan and (ii) $2,489 paid to our disability insurance plan.

73 
72 2023 Proxy Statement graphic


2020

TABLE OF CONTENTS

2022 Grants of Plan-Based Awards Table

The following table provides information concerning each grant of an award made in 20202022 for each of our Named Executive Officers under any plan. This information supplements the information about these awards set forth in the Summary Compensation Table.

NameType of
Award
Grant DateApproval
Date
Estimated Future Payouts Under Non-
Equity Incentive Plan Awards(1)
All Other Stock
Awards: Number of
Shares of Stock or
Units (#)
Grant Date Fair
Value of Stock
and Option
Awards ($)(2)
Threshold ($)Target ($)Maximum ($)
         
Hayden BrownCash1288,000N/A
RSU(3)2/29/20202/29/20207,98569,158
Jeff McCombsCash199,000(4)N/A
RSU(3)8/4/20208/4/2020274,3484,803,833
Brian KinionCash1145,600(5)N/A
RSU(3)2/29/20202/29/20205,54848,048
Eric GilpinCash1335,000(6)N/A
RSU(3)2/18/20202/18/2020107,758990,296

Name
Type of
Award
Grant
Date
Approval
Date
Estimated Future Payouts Under
Equity Incentive Plan Awards(1)
Estimated Future Payouts Under
Non-Equity Incentive Plan Awards(2)
All Other
Stock
Awards:
Number of
Shares of
Stock or
Units
(#)
All Other
Option
Awards:
Number of
Shares of
Stock or
Units
(#)
Exercise
Price of
Stock
Options
($/share)
Grant
Date Fair
Value of
Stock and
Option
Awards
($)(3)
Threshold
(#)
Target
(#)
Maximum
(#)
Threshold
($)
Target
($)
Maximum
($)
Hayden Brown
Cash
1
550,000
1,100,000
RSU
2/18/2022
2/16/2022
121,765
2,982,025
PSU
2/18/2022
2/16/2022
182,648
365,296
4,473,050
Jeff McCombs
Cash
1
400,000
800,000
RSU
2/18/2022
2/16/2022
114,155
2,795,656
PSU
2/18/2022
2/16/2022
76,103
152,207
1,863,762
RSU
8/18/2022
7/19/2022
12,171
225,894
Eric Gilpin
Cash
1
412,000
N/A
RSU
2/18/2022
2/16/2022
62,785
1,537,605
PSU
2/18/2022
2/16/2022
41,856
83,713
1,025,053
RSU
8/18/2022
7/19/2022
12,171
225,894
(1)
Reflects target bonus amounts
These columns show a range of outcomes possible under the PSU awards granted in 2022. The amount shown in the “Target” column represents the number of PSUs that would become Earned PSUs if the “target” level of performance was achieved for 2020our 2022 Compensation Program Revenue. The amount shown in the “Threshold” column represents the number of PSUs that would become Earned PSUs if the minimum level of performance was achieved for our 2022 Compensation Program Revenue before any PSUs are eligible to become Earned PSUs. The amount shown in the “Maximum” column represents the number of PSUs that would become Earned PSUs if the maximum level of performance was achieved for our 2022 Compensation Program Revenue. Further information about these awards is provided in the section titled “—Compensation Discussion and Analysis—Compensation Elements—2022 Equity Awards.”
(2)
These columns show a range of possible payouts under our 20202022 Performance Bonus Plan (except with respect to Mr. Gilpin), as described in “CompensationCompensation Discussion and Analysis—Compensation Elements—Annual Bonuses.Bonuses. Bonus amounts under the 2020 Performance Bonus Plan did not have a stated maximum amount. These amounts do not correspond to the actual amounts that were received by our Named Executive Officers. The actual amounts received by our Named Executive Officers were as follows: Ms. Brown, $365,760;$462,000; Mr. McCombs, $125,730 (which represents a pro-rated amount due to base salary payments only being earned during his partial year of employment); Mr. Kinion, $0; and Mr. Gilpin, $306,202.$269,568. The amount shown in the “Target” column represents the amount payable if the “target” level of performance was achieved for our 2022 Compensation Program Revenue. The amount shown in the “Threshold” column represents the amount payable if the minimum level of performance was achieved for our 2022 Compensation Program Revenue before any amounts become payable under our 2022 Performance Bonus Plan. The amount shown in the “Maximum” column represents the amount payable if the maximum level of performance was achieved for our 2022 Compensation Program Revenue.
(3)
(2)
The amounts reported in this column represent the grant date fair value of each award, granted under the 2018 Plan, as computedcalculated in accordance with ASC 718. The assumptions used in calculating the grant date fair value of the RSUs reported in this column are set forth inSee Note 119 to the auditedour consolidated financial statements included in our Annual Report on Form 10-K for the year ended December 31, 2020. Note that2022, for a discussion of the amountsrelevant assumptions used in calculating these amounts. For PSUs, the amount reported is based on the probable outcome of the applicable performance conditions, which reflects the target level of performance at the time of grant (i.e., based on 100% of performance). Each of Ms. Brown and Messrs. McCombs and Gilpin was granted RSUs and PSUs in these columns reflect2022 as described in the accounting cost for these awardssection titled “—Compensation Discussion and do not correspond to the actual economic value that may be received by our Named Executive Officers from the awards.
(3)Analysis—Compensation Elements—Long-Term Incentive Compensation—2022 Equity Awards.” The vesting of these RSUstock awards is detailed in the “OutstandingOutstanding Equity Awards at 20202022 Fiscal Year-End”Year-End table below.
(4)Mr. McCombs’s annual bonus award was pro-rated due to base salary payments only being earned during his partial year of employment.
(5)Mr. Kinion served as our Chief Financial Officer until August 2020. Target bonus amount reflects the target amount based on Mr. Kinion’s base salary assuming his continued service as our Chief Financial Officer.
(6)Reflects target bonus amount under Mr. Gilpin’s sales compensation plan, as described in “Compensation Discussion and Analysis—Compensation Elements—Sales Compensation Plan for Mr. Gilpin.”

74 
graphic2023 Proxy Statement 73

TABLE OF CONTENTS

Outstanding Equity Awards at 20202022 Fiscal Year-End Table

The following table presents, for each of the Named Executive Officers, information regarding outstanding stock options, RSUs, and RSUsPSUs held as of December 31, 2020.

   Option AwardsStock Awards
   Number of Securities
Underlying Unexercised
Options (#)
Option
Exercise
Option
Expiration
Number of
Shares or Units
of Stock That
Have Not Vested
(#)
Market Value of Shares
or Units of Stock That
Have Not Vested ($)(2)
NameGrant Date(1) Exercisable UnexercisablePrice ($)Date
          
Hayden Brown12/15/2011(3) 2,375 1.5212/14/2021
4/7/2014(3) 120,597 2.764/6/2024
9/25/2014(3) 20,965 3.047/24/2023
12/19/2014(3) 15,642 3.6712/18/2024
4/23/2015(3) 78,114 3.584/22/2025
12/23/2015(4) 43,334 1,6673.0312/22/2025
9/26/2017(5) 339,187 239,9333.689/25/2027
2/11/2019(6)  20,682713,943
5/3/2019(7)  34,7401,199,225
12/12/2019(8)  652,74222,532,654
Jeff McCombs8/4/2020(9)  274,3489,470,493
Brian Kinion  
Eric Gilpin4/20/2016(10) 153,333 16,6673.234/19/2026
2/6/2018(11) 6,667 43,3334.042/5/2028
2/18/2020(12)  87,5543,022,364

2022.
Option Awards
Stock Awards
Name
Grant
Date(1)
Number of
Securities
Underlying
Unexercised
Options
Exercisable
(#)
Number of
Securities
Underlying
Unexercised
Options
Unexercisable
(#)
Equity
Incentive
Plan Awards:
Number of
Securities
Underlying
Unexercised
Unearned
Options
(#)
Option
Exercise
Price
($)
Option
Expiration
Date
Number of
Shares or
Units of Stock
That Have
Not Vested
(#)
Market Value
of Shares or
Units of Stock
That Have
Not Vested
($)(2)
Equity Incentive
Plan Awards:
Number of
Unearned Shares,
Units, or Other
Rights That Have
Not Vested
(#)
Equity Incentive
Plan Awards:
Market or Payout
Value of Unearned
Shares, Units, or
Other Rights That
Have Not Vested
($)(2)
Hayden Brown
9/26/2017(3)
261,709
3.68
9/25/2027
5/3/2019(4)
3,860
40,298
12/12/2019(5)
217,581
2,271,546
1/18/2021(6)
1,500,000
38.80
1/17/2031
2/17/2021(7)
45,896
479,154
2/17/2021(8)
23,063
240,778
2/18/2022(9)
182,648
1,906,845
2/18/2022(10)
98,935
1,032,881
Jeff McCombs(11)
Eric Gilpin
4/20/2016(12)
170,000
3.23
4/19/2026
2/6/2018(13)
46,667
3,333
4.04
2/5/2028
2/18/2020(14)
33,675
351,567
2/17/2021(15)
2,353
24,565
2/17/2021(16)
4,731
49,392
2/18/2022(17)
41,856
436,977
2/18/2022(18)
51,013
532,576
8/18/2022(19)
9,129
95,307
(1)
Outstanding equity awards with a grant date of December 15, 2011, and September 25, 2014, were granted under the oDesk 2004 Stock Plan, which we refer to as the 2004 Plan. Outstanding equity awards with a grant date of April 7, 2014, or after September 25, 2014, and prior to August 30, 2018, the date the 2018 Plan became effective, were granted under our 2014 Equity Incentive Plan, which we refer to as the 2014 Plan. Outstanding equity awards with a grant date after August 30, 2018, were granted under the 2018 Plan. The vesting of all awards is subject to continued service on each vesting date, in addition to any additional vesting terms described below.
(2)
Represents the fair market value of the shares underlying the RSUs and PSUs as of December 31, 2020,2022, based on the closing price on Nasdaq of our common stock on December 31, 2020,30, 2022 (the last day of business of 2022), which was $34.52$10.44 per share.
(3)
ThisThe stock option was fully exercisable as of December 31, 2020.2022.
(4)
The RSUs will vest in equal installments of 1/16th of the total number of RSUs on each quarterly anniversary after May 18, 2019, over 16 quarters of continuous service, such that the RSU award shall vest in full four years from May 18, 2019, subject to Ms. Brown’s continued service. The RSUs are subject to acceleration upon certain events as described in “Potential Payments upon Termination or Change in Control.”
(5)
The RSUs will vest in equal installments of 1/16th of the total number of RSUs on each quarterly anniversary after December 18, 2019, over 16 quarters of continuous service, such that the RSU award shall vest in full four years from December 18, 2019, subject to Ms. Brown’s continued service. The RSUs are subject to acceleration upon certain events as described in “Potential Payments upon Termination or Change in Control.”
(6)
The stock option becomes exercisable at a rate of 1/60th ofvests as described in the shares of our common stock underlying the stock option each month following the January 1, 2016, exercisability commencement date.section titled “—Compensation Discussion and Analysis—Compensation Elements—Long-Term Incentive Compensation—2022 Equity Awards—Chief Executive Officer Performance Award.” The stock option is subject to acceleration upon certain events as described in the section titled “PotentialPotential Payments upon Termination or Change in Control.Control.
(7)
(5)
The stock option becomes exercisable at a rate of 1/60thearned PSUs will vest 25% on the first 18th of the shares of our common stock underlying the stock option each month following the September 26, 2017, exercisability commencement date.one-year anniversary of the date of grant and thereafter 1/16th of the earned PSUs shall vest on each quarterly anniversary thereafter, subject to Ms. Brown’s continued service. The stock option isPSUs are subject to acceleration upon certain events as described in the section titled “PotentialPotential Payments upon Termination or Change in Control.Control.
(8)
(6)
The RSUs will vest at a ratein equal installments of 1/12th16th of the sharestotal number of our common stock underlyingRSUs on each quarterly anniversary after February 18, 2021, over 16 quarters of continuous service, such that the RSUs each quarter beginning on JanuaryRSU award shall vest in full four years from February 18, 2020.2021, subject to Ms. Brown’s continued service. The RSUs are subject to acceleration upon certain events as described in “—Potential Payments upon Termination or Change in Control.Control.
(9)
The PSUs vest as described in the section titled “—Compensation Discussion and Analysis—Compensation Elements—Long-Term Incentive Compensation—2022 Equity Awards.” The PSUs are represented at the target amount of shares that may be earned under the awards (i.e., based on 100% of performance). The time vesting requirements of the PSUs are subject to acceleration upon certain events as described in “Potential Payments upon Termination or Change in Control.”
(7)
74 2023 Proxy Statement graphic

TABLE OF CONTENTS

(10)
The RSUs will vest at a ratein equal installments of 1/16th of the sharestotal number of our common stock underlyingRSUs on each quarterly anniversary after February 18, 2022, over 16 quarters of continuous service, such that the RSUs each quarter beginning on JuneRSU award shall vest in full four years from February 18, 2019.2022, subject to Ms. Brown’s continued service. The RSUs are subject to acceleration upon certain events as described in “—Potential Payments upon Termination or Change in Control.”
(8)The RSUs vest at a rate of 1/16th of the shares of our common stock underlying the RSUs each quarter beginning on March 18, 2020, subject to Ms. Brown’s continued employment as our Chief Executive Officer on each vesting date. The RSUs are subject to acceleration upon certain events as described in “Potential Payments upon Termination or Change in Control.”

(9)(11)
The RSUs vestOn September 21, 2022, we entered into the McCombs Transition Agreement with Mr. McCombs, and Mr. McCombs’s last day of employment was December 31, 2022. Accordingly, we determined that Mr. McCombs’s awards that were forfeited in connection with his departure on December 31, 2022 were not outstanding at a rate of 75% offiscal year end and are therefore excluded from the shares of our common stock underlying the RSUs on August 18, 2023, and an additional 6.25% of the shares of our common stock underlying the RSUs over the following four quarters. The RSUs are subject to acceleration upon certain events as described in “Potential Payments upon Termination or Change in Control.”Outstanding Equity Awards at Fiscal Year End table.
(10)(12)
The stock option becomeswas fully exercisable at a rateas of 20% of the shares of our common stock underlying the stock option one year following the April 20, 2016, exercisability commencement date and an additional 1/60th of the shares of our common stock underlying the stock option each month thereafter. The stock option is subject to acceleration upon certain events as described in the section titled “Potential Payments upon Termination or Change in Control.”December 31, 2022.
(13)
(11)
The stock option becomes exercisable at a rate of 1/60th of the shares of our common stock underlying the stock option each month following the February 6, 2018 exercisability commencement date anddate. The stock option is subject to acceleration upon certain events as described in “Potentialthe section titled “Potential Payments upon Termination or Change in Control.Control.
(14)
(12)
The RSUs will vest in equal installments of 1/16th of the total number of RSUs on each quarterly anniversary after February 18, 2020, over sixteen (16)16 quarters of continuous service, such that the RSU award shall vest in full four years from February 18, 2020, subject to Mr. Gilpin’s continued service. The RSUs are subject to acceleration upon certain events as described in “Potential Payments upon Termination or Change in Control.”

75 (15)
The earned PSUs will vest 25% on the first 18th of the month following the one-year anniversary of the date of grant and thereafter 1/16th of the earned PSUs shall vest on each quarterly anniversary thereafter, subject to Mr. Gilpin’s continued service. The PSUs are subject to acceleration upon certain events as described in “Potential Payments upon Termination or Change in Control.”
(16)
The RSUs will vest in equal installments of 1/16th of the total number of RSUs on each quarterly anniversary after February 18, 2021, over 16 quarters of continuous service, such that the RSU award shall vest in full four years from February 18, 2021, subject to Mr. Gilpin’s continued service. The RSUs are subject to acceleration upon certain events as described in “Potential Payments upon Termination or Change in Control.”
(17)
The PSUs vest as described in the section titled “—Compensation Discussion and Analysis—Compensation Elements—Long-Term Incentive Compensation—2022 Equity Awards.” The PSUs are represented at the target amount of shares that may be earned under the awards (i.e., based on 100% of performance). The time vesting requirements of the PSUs are subject to acceleration upon certain events as described in “Potential Payments upon Termination or Change in Control.”
(18)
The RSUs will vest in equal installments of 1/16th of the total number of RSUs on each quarterly anniversary after February 18, 2022, over 16 quarters of continuous service, such that the RSU award shall vest in full four years from February 18, 2022, subject to Mr. Gilpin’s continued service. The RSUs are subject to acceleration upon certain events as described in “Potential Payments upon Termination or Change in Control.”
(19)
The RSUs will vest in equal installments of 1/4th of the total number of RSUs on each quarterly anniversary after August 18, 2022, over 4 quarters of continuous service, such that the RSU award shall vest in full one year from August 18, 2022, subject to Mr. Gilpin’s continued service. The RSUs are subject to acceleration upon certain events as described in “Potential Payments upon Termination or Change in Control.”

20202022 Stock Option Exercises and Stock Vested Table

The following table presents, for each of our Named Executive Officers, the number of shares of our common stock acquired upon the exercise of stock options or vesting and settlement of RSUs during 20202022 and the aggregate value realized upon the exercise of stock options and the vesting and settlement of RSUs.

 Option AwardsStock Awards
NameNumber of Shares Acquired
on Exercise (#)
Value Realized on
Exercise ($)(1)
Number of Shares
Acquired on Vesting (#)
Value Realized on
Vesting ($)(2)
     
Hayden Brown251,3464,417,883
Jeff McCombs
Brian Kinion700,00013,243,7385,54848,073
Eric Gilpin100,0002,472,67120,204426,042

Option Awards
Stock Awards
Name
Number of Shares
Acquired on
Exercise
(#)
Value Realized
on Exercise
($)
Number of Shares
Acquired on
Vesting
(#)
Value Realized
on Vesting
($)(1)
Hayden Brown
312,135
5,443,130
Jeff McCombs
189,776(2)
2,766,993
Eric Gilpin
45,686
805,096
(1)The aggregate value realized upon the exercise of a stock option represents the difference between the aggregate market price of the shares of our common stock on the date of exercise and the aggregate exercise price of the stock option. Amounts shown are presented on an aggregate basis for all exercises that occurred during 2020.
(2)
The aggregate value realized upon the vesting and settlement of an RSU is based on the closing price on Nasdaq of our common stock on the date prior to the day of vesting.vesting date. Amounts shown are presented on an aggregate basis for all vesting and settlement that occurred during 2020.2022.
(2)
Pursuant to the terms of the McCombs Transition Agreement, Mr. McCombs’s Initial RSU Award was deemed vested with respect to 137,174 shares upon execution of the McCombs Transition Agreement on September 29, 2022 and an additional 17,146 shares following November 18, 2022. The deemed vesting of the 137,174 shares upon execution of the McCombs Transition Agreement and the additional 17,146 shares following November 18, 2022 were consistent with the terms of Mr. McCombs’s offer letter, which provided for acceleration of the Initial RSU Award after one year if Mr. McCombs were to be terminated without cause or resigned for good reason.
graphic2023 Proxy Statement 75

TABLE OF CONTENTS

Offer Letters

We have entered into offer letters with Ms. Brown and Messrs. McCombs andMr. Gilpin, and we had entered into an offer letter with Mr. KinionMcCombs prior to the termination of his employment in October 2020.December 2022. Each of these offer letters provides (or provided, in the case of Mr. Kinion)McCombs) for at-will employment and generally includes the Named Executive Officer’s initial base salary and an indication of eligibility for an annual bonus award opportunity. In addition, while employed, each of our Named Executive Officers is eligible to participate in our annual performance bonus plan (other than Mr. Gilpin who participates in a separate sales compensation plan), a disability plan, and employee benefit plans, including health insurance, that we offer to our employees. In addition, each of our Named Executive Officers executed a form of our standard confidential information and invention assignment agreement upon the commencement of their employment. Any potential payments and benefits due upon a termination of employment or a change in control are further described in the following section “Potential Payments upon Termination or Change in Control.”

76 

In March 2023, we entered into an offer letter with Ms. Gessert in connection with her appointment as our Chief Financial Officer, a copy of which will be filed as an exhibit to our Quarterly Report on Form 10-Q for the quarter ended March 31, 2023.

Potential Payments upon Termination or Change in Control

We have entered into change in control and severance agreementsa Severance Agreement with each of our Named Executive Officers, which provideprovides for the following benefits if the Named Executive Officer is terminated by us without “cause”cause (as defined in the Severance Agreements) or, with respect to our President and Chief Executive Officer only, by the Named Executive Officer for “good reason”good reason (as defined in the Severance Agreements), outside of a change in control (as defined in the Severance Agreements) in exchange for a customary release of claims: (i) a lump sum severance payment of six months base salary (12 months for our President and Chief Executive Officer); (ii) payment of premiums for continued medical benefits for up to six months (12 months for our President and Chief Executive Officer); and (iii) in the case of our President and Chief Executive Officer only, 50% acceleration of any then-unvested equity awards (excluding equity awards that vest, in whole or in part, upon satisfaction of performance criteria).

If the Named Executive Officer’s employment is terminated by us without cause (as defined in the change in control and severance agreements)Severance Agreements) or by the executive for good reason (as defined in the change in control and severance agreements)Severance Agreements) within the three months preceding a change in control (as defined in the change in control and severance agreements)Severance Agreements) (but after a legally binding and definitive agreement for a potential change in control has been executed) or within the 12 months following a change in control, the change in control and severance agreementsSeverance Agreements provide the following benefits in exchange for a customary release of claims: (i) a lump sum severance payment of 12 months base salary (18 months for our President and Chief Executive Officer); (ii) a lump sum payment equal to the Named Executive Officer’s then-current target bonus opportunity;opportunity on a pro-rated basis; (iii) 100% acceleration of any then-unvested equity awards (excluding equity awards that vest, in whole or in part, upon satisfaction of performance criteria); and (iv) payment of premiums for continued medical benefits for up to 12 months (18 months for our President and Chief Executive Officer). Each change in control and severance agreementSeverance Agreement is in effect for three years, with automatic renewals for new three-year periods unless notice is given by us to the Named Executive Officer three months prior to expiration.

An award agreement for equity awards that vest upon satisfaction of performance criteria may provide for acceleration upon a change in control.

The benefits under the change in control and severance agreementsSeverance Agreements supersede all other cash severance and vesting acceleration arrangements (excluding equity awards that vest, in whole or in part, upon satisfaction of performance criteria, which will be governed by the terms of the applicable performance-based equity awards).

In exchange for the benefits under the change in control and severance agreements,Severance Agreements, each Named Executive Officer agrees to a general release of claims and compliance with a non-disparagement covenant for a period of 24 months following separation from us.
76 2023 Proxy Statement graphic

TABLE OF CONTENTS

As a result of the termination of his employment, Mr. Kinion is no longer entitled to receive the benefits described above under the change in control and severance agreements.

The following table provides information concerning the estimated payments and benefits that would be provided in the circumstances described above for each of our Named Executive Officers. Except where otherwise noted, payments and benefits are estimated assuming that the triggering event took place on December 31, 2020,2022, and the price per share of our common stock was the closing price on Nasdaq as of December 31, 2020,30, 2022 (the last day of business of 2022), which was $34.52.$10.44. There can be no assurance that a triggering event would produce the same or similar results as those estimated below if such event occurs on any other date or at any other price, or if any other assumption used to estimate potential payments and benefits is not correct. Due to the number of factors that affect the nature and amount of any potential payments or benefits, any actual payments and benefits may be different.

77 

 Qualifying Termination - No Change in ControlQualifying Termination - Change in Control
NameCash
Severance
($)(1)
Continuation
of Medical
Benefits ($)
Value of
Accelerated
Vesting ($)(2)
Total ($)Cash Severance
($)(1)
Bonus
Payment ($)(3)
Continuation
of Medical
Benefits ($)
Value of
Accelerated
Vesting ($)(2)
Total ($)
          
Hayden Brown480,00031,09115,948,92416,460,015720,000288,00046,63631,897,84932,952,485
Jeff McCombs200,00013,756213,756400,00099,000(4)27,5129,470,4939,997,005
Brian Kinion(5)
Eric Gilpin167,50013,756181,256335,000335,00027,5124,864,6645,562,176

Qualifying Termination - No Change in Control
Qualifying Termination - Change in Control
Name
Cash
Severance
($)(1)
Continuation
of Medical
Benefits ($)
Value of
Accelerated
Vesting ($)(2)
Total ($)
Cash
Severance
($)(1)
Bonus
Payment
($)(3)
Continuation
of Medical
Benefits ($)
Value of
Accelerated
Vesting ($)(2)
Total ($)
Hayden Brown
550,000
33,585
2,833,202
3,416,787
825,000
550,000
50,378
5,666,404
7,091,782
Jeff McCombs(4)
Eric Gilpin
206,000
14,808
220,808
412,000
412,000
29,616
1,441,798
2,295,414
(1)
The severance amount related to base salary was determined based on the base salaries in effect on December 31, 2020.2022.
(2)
The value of accelerated vesting is calculated based on the per share closing price on Nasdaq as of December 31, 2020,30, 2022 (the last day of business of 2022), which was $34.52,$10.44, less, if applicable, the aggregate exercise price of each outstanding unexercisableunvested stock option. For PSUs, the amount reported is based on a reasonable estimate of the applicable performance conditions (i.e., based on 84% of performance). The CEO Performance Award was not included, as the exercise price for such award was above the per share closing price of our common stock on Nasdaq as of December 30, 2022 (the last day of business of 2022).
(3)
The value of the bonus payment was determined based on the full amount of the target bonuses in effect on December 31, 2020.2022.
(4)
On September 21, 2022, we entered into the McCombs Transition Agreement with Mr. McCombs, and Mr. McCombs’s annual bonus awardlast day of employment was pro-rated dueDecember 31, 2022. Accordingly, we determined that Mr. McCombs was not entitled to base salary payments only being earned during his partial year of employment.
(5)Mr. Kinion’s employment ended on October 1, 2020. The amounts presented for Mr. Kinion reflect theany estimated payments and benefits that would be provided in the circumstances described above at fiscal year end and such amounts are therefore excluded from the Potential Payments upon Termination or Change in Control table.
In April 2023, we entered into a Severance Agreement with Ms. Gessert in connection with her appointment as our Chief Financial Officer, a copy of which will be filed as an exhibit to our Quarterly Report on Form 10-Q for the quarter ended March 31, 2023.
graphic2023 Proxy Statement 77

TABLE OF CONTENTS

Pay Versus Performance
As required by Section 953(a) of the Dodd-Frank Wall Street Reform and Consumer Protection Act and Item 402(v) of Regulation S-K, we are providing the following information about the relationship between executive compensation actually paid, which we refer to as CAP, and certain financial performance of our company and peers. For further information concerning our variable pay-for-performance philosophy and how we align executive compensation with our performance, refer to “Executive Compensation—Compensation Discussion and Analysis.”
Pay Versus Performance
Value of Initial Fixed $100 Investment Based on:
Year(1)
Summary
Compensation
Table Total
for
PEO(2)
($)
Compensation
Actually Paid
to PEO(3)
($)
Average
Summary
Compensation
Table Total
for
Non-PEO
NEOs(2)
($)
Average
Compensation
Actually Paid
to Non-PEO
NEOs(4)
($)
Upwork Total
Shareholder
Return(5)
($)
Peer Group
Total
Shareholder
Return(6)
($)
Net Loss(7)
($)
Company-
Selected
Measure:
Compensation Program Revenue(8)
($)
2022
8,474,727
(25,586,673)
4,573,989
(3,208,186)
98
108
(89,885,000)
618,318,000
2021
34,909,304
29,693,025
2,116,323
1,991,129
320
178
(56,240,000)
470,925,703
2020
848,412
25,983,464
2,441,919
4,223,757
324
140
(22,867,000)
344,924,258
(1)
Hayden Brown served as our principal executive officer, which we refer to as our PEO, for the entirety of 2020, 2021 and 2022, and our non-PEO named executive officers, which we refer to as our Non-PEO NEOs, for the applicable years were as follows: (i) for 2022: Eric Gilpin and Jeff McCombs; (ii) for 2021: Eric Gilpin and Jeff McCombs; and (iii) 2020: Eric Gilpin, Jeff McCombs, and Brian Kinion.
(2)
Amounts reported in these columns represent (i) the total compensation reported in the Summary Compensation Table for the applicable year for our PEO and (ii) the average of the total compensation reported in the Summary Compensation Table for the applicable year for our Non-PEO NEOs.
(3)
Amounts reported in this column represent CAP to Hayden Brown as our PEO in the indicated fiscal years, as calculated per Item 402(v) of Regulation S-K. Such calculations are based on Ms. Brown’s total compensation reported in the Summary Compensation Table for the indicated fiscal years and adjusted as shown in the table below. In making each of these adjustments, the “value” of an option or stock award is the fair value of the award on the applicable date determined in accordance with FASB ASC Topic 718 using the valuation assumptions we then used to calculate the fair value of our equity awards. For more information on the valuation of our equity awards, please see the notes to our financial statements that appear in our applicable Annual Report on Form 10-K and the footnotes to the Summary Compensation Table that appears in our applicable definitive proxy statement. The dollar amounts do not reflect the actual amount of compensation the Company considers to be earned by or paid to Ms. Brown during the applicable year. There were no dividends paid and no changes to the value of pension benefits as we do not provide pension benefits.
78 2023 Proxy Statement graphic

TABLE OF CONTENTS

PEO
2020
($)
2021
($)
2022
($)
Summary Compensation Table—Total Compensation
(a)
848,412
34,909,304
8,474,727
Subtract Amounts Reported Under the “Stock Awards” and “Option Awards” Columns in the Summary Compensation Table for Applicable Fiscal Year
(b)
(33,406,652)
(7,455,075)
Add Fair Value of Awards Granted During Applicable Fiscal Year that Remain Unvested as of Applicable Fiscal Year End, Determined as of Applicable Fiscal Year End
(c)
23,631,900
3,178,100
Add/Subtract Awards Granted During Prior Fiscal Years that were Outstanding and Unvested as of Applicable Fiscal Year End, Determined Based on Change in Fair Value from Prior Fiscal Year End to Applicable Fiscal Year End
(d)
22,547,000
(190,309)
(25,451,923)
Add Fair Value of Awards Granted During Applicable Fiscal Year that Vested as of Applicable Fiscal Year End, Determined as of Applicable Vesting Date
(e)
69,150
319,445
748,542
Add/Subtract Awards Granted During Prior Fiscal Years that Vested During Applicable Fiscal Year, Determined Based on Change in Fair Value from Prior Fiscal Year End to Vesting Date
(f)
2,518,902
4,429,337
(5,081,044)
Subtract Fair Value of Awards Granted During Prior Fiscal Years that were Forfeited During Applicable Fiscal Year, Determined as of Prior Fiscal Year End
(g)
Compensation Actually Paid
25,983,464
29,693,025
(25,586,673)
(a)
Represents Total Compensation as reported in the Summary Compensation Table for the indicated fiscal year.
(b)
Represents the aggregate grant date fair value of the stock awards and option awards granted to Hayden Brown during the indicated fiscal year, computed in accordance with FASB ASC 718. Amounts shown are the amounts reported in the Summary Compensation Table.
(c)
Represents the aggregate fair value as of the indicated fiscal year-end of Hayden Brown’s outstanding and unvested stock awards and option awards granted during such fiscal year, computed in accordance with FASB ASC 718.
(d)
Represents the aggregate change in fair value during the indicated fiscal year of the outstanding and unvested stock awards and option awards granted in prior fiscal years and held by Hayden Brown as of the last day of the indicated fiscal year, computed in accordance with FASB ASC 718.
(e)
Represents the aggregate fair value at vesting of the option and stock awards that both were granted to Hayden Brown and vested during the indicated fiscal year, computed in accordance with FASB ASC 718.
(f)
Represents the aggregate change in fair value, measured from the prior fiscal year-end to the vesting date, of each stock award and option award held by Hayden Brown that was granted in a prior fiscal year and vested during the indicated fiscal year, computed in accordance with FASB ASC 718.
(g)
Represents the aggregate fair value as of the last day of the prior fiscal year of Hayden Brown’s stock awards and option awards that were granted in a prior fiscal year and failed to meet the applicable vesting conditions in the indicated fiscal year, computed in accordance with FASB ASC 718.
(4)
Amounts reported in this column represent the average CAP to our Non-PEO NEOs in the indicated fiscal year, as calculated per Item 402(v) of Regulation S-K. Such calculations are based on the average total compensation for such Non-PEO NEOs reported in the Summary Compensation Table for the indicated fiscal year and adjusted as shown in the table below. In making each of these adjustments, the “value” of an option or stock award is the fair value of the award on the applicable date determined in accordance with FASB ASC Topic 718 using the valuation assumptions we then used to calculate the fair value of our equity awards. For more information on the valuation of our equity awards, please see the notes to our financial statements that appear in our applicable Annual Report on Form 10-K and the footnotes to the Summary Compensation Table that appears in our applicable definitive proxy statement. The dollar amounts do not reflect the actual amount of compensation the Company considers to be earned by or paid to our Non-PEO NEOs during the applicable year. There were no dividends paid and no changes to the value of pension benefits as we do not provide pension benefits.
graphic2023 Proxy Statement 79

TABLE OF CONTENTS

Non-PEO NEO Average*
2020
($)
2021
($)
2022
($)
Summary Compensation Table—Total Compensation
(a)
2,441,919
2,116,323
4,573,989
Subtract Amounts Reported Under the “Stock Awards” and “Option Awards” Columns in the Summary Compensation Table for Applicable Fiscal Year
(b)
(1,931,376)
(1,126,933)
(3,836,932)
Add Fair Value of Awards Granted During Applicable Fiscal Year that Remain Unvested as of Applicable Fiscal Year End, Determined as of Applicable Fiscal Year End
(c)
4,164,286
579,986
538,543
Add/Subtract Awards Granted During Prior Fiscal Years that were Outstanding and Unvested as of Applicable Fiscal Year End, Determined Based on Change in Fair Value from Prior Fiscal Year End to Applicable Fiscal Year End
(d)
467,619
62,360
507,769
Add Fair Value of Awards Granted During Applicable Fiscal Year that Vested as of Applicable Fiscal Year End, Determined as of Applicable Vesting Date
(e)
158,029
124,483
345,331
Add/Subtract Awards Granted During Prior Fiscal Years that Vested During Applicable Fiscal Year, Determined Based on Change in Fair Value from Prior Fiscal Year End to Vesting Date
(f)
178,525
359,630
(1,988,433)
Subtract Fair Value of Awards Granted During Prior Fiscal Years that were Forfeited During Applicable Fiscal Year, Determined as of Prior Fiscal Year End
(g)
(1,255,245)
(2,332,916)
Compensation Actually Paid
4,223,757
1,991,129
(3,208,186)
*
Please see footnote 1 above for the Non-PEO NEOs included in the average for each indicated fiscal year.
(a)
Represents the average Total Compensation as reported in the Summary Compensation Table for the Non-PEO NEOs in the indicated fiscal year.
(b)
Represents the average aggregate grant date fair value of the stock awards and option awards granted to the Non-PEO NEOs during the indicated fiscal year, computed in accordance with FASB ASC 718. Amounts shown are the amounts reported in the Summary Compensation Table.
(c)
Represents the average aggregate fair value as of the indicated fiscal year-end of the Non-PEO NEOs’ outstanding and unvested stock awards and option awards granted during such fiscal year, computed in accordance with FASB ASC 718.
(d)
Represents the average aggregate change in fair value during the indicated fiscal year of the outstanding and unvested stock awards and option awards granted in prior fiscal years and held by the Non-PEO NEOs as of the last day of the indicated fiscal year, computed in accordance with FASB ASC 718.
(e)
Represents the average aggregate fair value at vesting of the stock awards and option awards that were both granted to the Non-PEO NEOs and vested during the indicated fiscal year, computed in accordance with FASB ASC 718.
(f)
Represents the average aggregate change in fair value, measured from the prior fiscal year-end to the vesting date, of each stock award and option award held by the Non-PEO NEOs that was granted in a prior fiscal year and vested during the indicated fiscal year, computed in accordance with FASB ASC 718.
(g)
Represents the average aggregate fair value as of the last day of the prior fiscal year of the Non-PEO NEOs’ stock awards and option awards that were granted in a prior fiscal year and failed to meet the applicable vesting conditions in the indicated fiscal year, computed in accordance with FASB ASC 718. On September 21, 2022, we entered into the McCombs Transition Agreement with Non-PEO NEO Jeff McCombs, and Mr. McCombs’s last day of employment was December 31, 2022. Accordingly, we determined that Mr. McCombs’s awards that were forfeited in connection with his departure on December 31, 2022 were not outstanding at fiscal year end and are therefore included in this calculation row.
(5)
Pursuant to rules of the SEC, the comparison assumes $100 was invested in our common stock on December 31, 2019, using the closing stock price of the end of the last day that was prior to the beginning of our fiscal year 2020. Historic stock price performance is not necessarily indicative of future stock price performance. There were no dividends or other earnings paid in the covered fiscal years.
(6)
The TSR Peer Group consists of the Nasdaq 100 Technology Index which we also use in the stock performance graph required by Item 201(e) of Regulation S-K included in our Annual Report for the year ended December 31, 2022. This column assumes $100 was invested in this peer group on December 31, 2019 (same period as used for footnote 5 above).
(7)
The amounts shown in this column are also included in our audited financial statements.
(8)
Our compensation committee determined Compensation Program Revenue to be the most important financial performance measure used to link company performance to CAP to our PEO and Non-PEO NEOs for 2022 because, in its view, it was most consistent with our near-term objective of driving revenue growth. Compensation Program Revenue achievement was the sole driver of payouts under our 2022 Performance Bonus Plan and was the sole performance metric underlying the PSUs granted to our PEO and Non-PEO NEOs in 2022. Compensation Program Revenue is not a financial measure prepared in accordance with GAAP. For more information on how we compute this non-GAAP financial measure and a reconciliation to the most directly comparable financial measure prepared in accordance with GAAP, please refer to “Appendix B: Reconciliation of Non-GAAP Financial Measures” in this Proxy Statement.
80 2023 Proxy Statement graphic

TABLE OF CONTENTS

Relationship Between Pay and Performance
CAP, as calculated per Item 402(v) of Regulation S-K, reflects cash compensation actually paid as well as adjusted values to unvested and vested equity awards during the years shown in the table based on year-end or vesting date stock prices, various accounting valuation assumptions, and projected performance modifiers. Due to how CAP is calculated, the CAP as reported for each year does not reflect the actual amounts earned by our NEOs from their equity awards. CAP generally fluctuates annually due to the change in our stock price from year to year as well as varying levels of actual achievement of performance goals.
Because CAP does not reflect the actual amount of compensation earned by our PEO and Non-PEO NEOs, we do not use this measure for understanding how NEO pay aligns with our performance. For a discussion of how our compensation committee assessed “pay-for-performance” and how our executive compensation program is designed to link executive compensation with the achievement of our financial and strategic objectives as well as stockholder value creation each year, see “Compensation Discussion and Analysis” in this Proxy Statement and in our definitive proxy statements filed with the SEC on April 20, 2021 and April 19, 2022.
Below are graphs showing the relationship of CAP to our PEO and Non-PEO NEOs for our fiscal years 2020, 2021 and 2022 to (1) TSR of both our common stock and the Nasdaq 100 Technology Index, (2) our net loss, and (3) our Compensation Program Revenue (as described in footnote 8 above).
graphic
graphic2023 Proxy Statement 81

TABLE OF CONTENTS

graphic
graphic
Tabular List of Financial Performance Measures for 2022
The following table contains the most important financial measures used to link CAP, for the year ended December 31, 2022, to the Company’s performance. No other financial performance metrics were used by us to link CAP to our PEO or Non-PEO NEOs in 2022 to company performance.

Most Important Financial Performance Measures for 2022
Compensation Program Revenue(1)
Annual enterprise revenue quota (with respect to Mr. Kinion assumingGilpin)(2)
Annual enterprise bookings quota (with respect to Mr. Gilpin)(2)
(1)
Compensation Program Revenue is the triggering event took place while heprimary financial performance metric used to link CAP to our PEO and Non-PEO NEOs in 2022 to company performance. Compensation Program Revenue achievement was stillthe sole driver of payouts under our Chief Financial Officer.2022 Performance Bonus Plan and was the sole performance metric underlying the PSUs granted to our PEO and Non-PEO NEOs in 2022.
(2)
Mr. Gilpin’s annual cash incentive under the sales compensation plan for performance in 2022 paid out based on achievement of annual enterprise revenue quota and annual enterprise bookings quota.
82 2023 Proxy Statement graphic

TABLE OF CONTENTS

Limitations on Liability and Indemnification Matters

Our restated certificate of incorporation contains provisions that limit the liability of our directors for monetary damages to the fullest extent permitted by the DGCL. Consequently, our directors are not personally liable to us or our stockholders for monetary damages for any breach of fiduciary duties as directors, except liability for:

any breach of the director’s duty of loyalty to us or our stockholders;
any act or omission not in good faith or that involves intentional misconduct or a knowing violation of law;
unlawful payments of dividends or unlawful stock repurchases or redemptions as provided in Section 174 of the DGCL; or
any transaction from which the director derived an improper personal benefit.

any breach of the director’s duty of loyalty to us or our stockholders;
any act or omission not in good faith or that involves intentional misconduct or a knowing violation of law;
unlawful payments of dividends or unlawful stock repurchases or redemptions as provided in Section 174 of the DGCL; or
any transaction from which the director derived an improper personal benefit.
Further, if the Restated Certificate of Incorporation described in Proposal 4 is approved by our stockholders, we will provide for the exculpation of officers, to the fullest extent permitted by law, including for personal liability for breach of fiduciary duty. This exculpation would not protect officers from liability for breach of the duty of loyalty, acts, or omissions not in good faith or that involve intentional misconduct or a knowing violation of law or any transaction in which the officer derived an improper personal benefit. Nor would this exculpation shield such officers from liability for claims brought by or in the right of our company, such as derivative claims. Our current restated certificate of incorporation and our amended and restated bylaws require us to indemnify our directors and officers to the maximum extent not prohibited by the DGCL and allow us to indemnify other employees and agents as set forth in the DGCL. Subject to certain limitations, our amended and restated bylaws also require us to advance expenses incurred by our directors and officers for the defense of any action for which indemnification is required or permitted, subject to very limited exceptions.

We have entered, and intend to continue to enter, into separate indemnification agreements with our directors, officers, and our key employees. These agreements, among other things, require us to indemnify our directors, officers, and key employees for certain expenses, including attorneys’ fees, judgments, fines, and settlement amounts actually and reasonably incurred by these individuals in any action or proceeding arising out of their service to us or any of our subsidiaries or any other company or enterprise to which these individuals provide services at our request. Subject to certain limitations, our indemnification agreements also require us to advance expenses incurred by our directors, officers, and key employees for the defense of any action for which indemnification is required or permitted.

We believe that these provisions of our restated certificate of incorporation, amended and restated bylaws, and indemnification agreements are necessary to attract and retain qualified directors, officers, and key employees. We also maintain directors’ and officers’ liability insurance.

The limitation of liability and indemnification provisions in our restated certificate of incorporation and amended and restated bylaws or in these indemnification agreements may discourage stockholders from bringing a lawsuit against our directors and officers for breaches of their fiduciary duty. They may also reduce the likelihood of derivative litigation against our directors and officers, even though an action, if successful, might benefit us and other stockholders. Further, a stockholder’s investment may be adversely affected to the extent that we pay the costs of settlement and damage awards against directors and officers as required by these indemnification provisions.

Insofar as indemnification for liabilities arising under the Securities Act may be permitted for directors, executive officers, or persons controlling us, we have been informed that, in the opinion of the SEC, such indemnification is against public policy as expressed in the Securities Act and is therefore unenforceable.

78 
graphic2023 Proxy Statement 83

CEO Pay Ratio Disclosure

In accordance with Item 402(u) of Regulation S-K, we are providing below disclosure relating to the ratio of the annual total compensation of our President and Chief Executive Officer, Ms. Brown, to the median of the annual total compensation of all of our employees (except for our Chief Executive Officer).

, which we refer to as the CEO Pay Ratio.

For 2020:

The annual total compensation of our Chief Executive Officer, Ms. Brown, was $848,412;

The median of the annual total compensation of all our employees (except for our Chief Executive Officer) was $193,227; and

The ratio of the annual total compensation of our Chief Executive Officer to the median of the annual total compensation of all our employees (except for our Chief Executive Officer) was 4 to 1.

2022:

The annual total compensation of our Chief Executive Officer, Ms. Brown, was $8,474,727, as reported in the “Total” column of the Summary Compensation Table;
The median of the annual total compensation of all our employees (except for our Chief Executive Officer) was $300,716; and
The CEO Pay Ratio was 28 to 1.
This ratio is a reasonable estimate calculated in a manner consistent with SEC rules.

With respect to

For a description of our methodology for identifying the median employee, see “CEO Pay Ratio Disclosure” on pages 79 and 80 of our definitive proxy statement filed with the SEC on April 20, 2021.
We then calculated the annual total compensation of our Chief Executive Officer,for this individual using the same methodology we useduse to calculate the amount reported for our CEO in the “Total” column of the 2020 Summary Compensation Table.

Ms. Brown was appointed as our President and Chief Executive Officer effective January 1, 2020. In connection with this appointment, Ms. Brown was granted an RSU award in December 2019. Accordingly, Ms. Brown did not receive an equity award in 2020, other than the grant of a fully-vested RSU award issued in February 2020 pursuant to our 2019 Performance Bonus Plan. We expect that the pay ratio disclosed for 2021 will be greater than the pay ratio for 2020. For example, if Ms. Brown’s RSU award granted in December 2019 had been included in the determination of this pay ratio disclosure, such ratio would have been 61 to 1.

To identify our median employee, we took the following steps:

We selected December 31, 2020, the last day of our 2020 fiscal year, as the determination date for purposes of identifying our median employee.

As of December 31, 2020, our employee population consisted of approximately 538 individuals (except for our Chief Executive Officer) working at our parent company and consolidated subsidiaries, which included all employees whether employed on a full-time or part-time basis, including two employees located outside the United States. We did not include any contractors or other non-employee workers in our employee population.

Compensation was measured over the 12-month period beginning on January 1, 2020 and ending on December 31, 2020. We selected our median employee using a compensation measure that consisted of actual base salary earned during 2020, actual bonus or commission paid for 2020, and the grant date fair value of equity awards granted in 2020. We selected the foregoing compensation elements because they represented our principal broad-based compensation elements.

79 

We annualized the cash compensation for full-time and part-time permanent employees who were hired during 2020, but did not work for us the entire year.

All employees except for our Chief Executive Officer were ranked from lowest to highest with the median determined from this list.

Once we identified our median employee, we determined that employee’s annual total compensation in the same manner that we calculated the total compensation of our Chief Executive Officer for purposes of the 20202022 Summary Compensation Table and compared the two to determine the pay ratio.

as set forth in this Proxy Statement.

Because SEC rules for identifying the median compensated employee allow companies to adopt a variety of methodologies, to apply certain exclusions, and to make reasonable estimates and assumptions that reflect their employee populations and compensation practices, the pay ratio reported by other companies may not be comparable to the pay ratio reported above, as other companies have different employee populations and compensation practices and may use different methodologies, exclusions, estimates, and assumptions in calculating their own pay ratios.

80 
84 2023 Proxy Statement graphic


EQUITY COMPENSATION PLAN INFORMATION

TABLE OF CONTENTS

Equity Compensation Plan Information
The following table presents information as of December 31, 2020,2022, with respect to compensation plans under which shares of our common stock may be issued.

Plan categoryNumber of securities to be issued upon exercise or vesting and settlement of outstanding securities (#)Weighted-average exercise price per share of outstanding options ($)Number of securities remaining available for future issuance under equity compensation plans (excluding securities reflected in column (a)) (#)
(a)(b)(c)
    
Equity compensation plans approved by security holders10,426,815(1)     3.83(2)20,751,919(3)
Equity compensation plans not approved by security holders N/A  
Total10,426,815 3.83 20,751,919 

Plan category
Number of securities to be issued
upon exercise or vesting and
settlement of outstanding
securities (#)
Weighted-average exercise
price per share of outstanding
options ($)
Number of securities remaining
available for future issuance under
equity compensation plans
(excluding securities reflected in
column (a)) (#)
(a)
(b)
(c)
Equity compensation plans approved by security holders
11,765,632(1)
17.58(2)
26,617,736(3)
Equity compensation plans not approved by security holders
— 
— 
— 
Total
11,765,632
17.58
26,617,736
(1)
Includes the oDesk 2004 Stock Plan, which we refer to as the 2004 Plan, the Elance 2009 Stock Option Plan, which we refer to as the 2009 Plan, the 2014 Plan, and the 2018 Plan. Excludes purchase rights accruing under the 2018 Employee Stock Purchase Plan, which we refer to as the 2018 ESPP. For awards with performance-based vesting conditions, including PSUs and the CEO Performance Award, the amount reported is based on the maximum outcome of the applicable performance condition (i.e., based on 200% of performance for PSUs).
(2)
The weighted-average exercise price does not reflect the shares that will be issued in connection with the settlement of RSUs or PSUs, since RSUs and PSUs have no exercise price.
(3)
Includes 18,332,76522,823,608 shares of our common stock available for issuance under the 2018 Plan as of December 31, 2020,2022, and 2,419,1543,794,128 shares of our common stock available for issuance under the 2018 ESPP as of December 31, 2020.2022. There were no shares of common stock available for issuance under the 2004 Plan, the 2009 Plan, or the 2014 Plan as of December 31, 2020,2022, but those plans will continue to govern the terms of stock options granted thereunder. Any shares of common stock that are subject to outstanding awards under the 2004 Plan, the 2009 Plan, or the 2014 Plan that are issuable upon the exercise of stock options that expire or become unexercisable for any reason without having been exercised in full will generally be available for future grant and issuance as shares of common stock under the 2018 Plan. In addition, the number of shares reserved for issuance under the 2018 Plan increased automatically by 6,239,7616,618,413 shares on January 1, 2021,2023, and will increase automatically on the first day of January of each of 20222024 through 2028 by the number of shares equal to 5% of the total issued and outstanding shares of our common stock as of the immediately preceding December 31 or a lower number approved by our board of directors or our compensation committee. The number of shares reserved for issuance under the 2018 ESPP increased automatically by 998,3611,058,946 shares on January 1, 2021,2023 and will increase automatically on the first day of January of each year during the term of the 2018 ESPP by the number of shares equal to 0.8% of the total outstanding shares of our common stock as of the immediately preceding December 31 or a lower number approved by our board of directors or our compensation committee.

81 
graphic2023 Proxy Statement 85


CERTAIN RELATIONSHIPS AND RELATED PARTY TRANSACTIONS

TABLE OF CONTENTS

Certain Relationships and Related Party Transactions
A “related person transaction” is a transaction, arrangement, or relationship in which we or any of our subsidiaries was, is, or will be a participant, the amount of which exceeds $120,000, and in which any related person had, has, or will have a direct or indirect material interest. A “related person” means:
any person who is, or at any time since the beginning of our last fiscal year was, a director or executive officer of our company or a nominee to become a director;
any person who is known by us to be the beneficial owner of more than 5% of our voting securities; and
any immediate family member of any of the foregoing persons, which means any child, stepchild, parent, stepparent, spouse, sibling, mother-in-law, father-in-law, son-in-law, daughter-in-law, brother-in-law, or sister-in-law of a director, director nominee, executive officer, or beneficial owner of more than 5% of our voting securities, and any person (other than a tenant or employee) sharing the household of such director, director nominee, executive officer, or beneficial owner of more than 5% of our voting securities.
In addition to the executive officer and director compensation arrangements discussed above under “Executive Compensation” and “Proposal No. 1—Election of Directors—20202022 Director Compensation,” respectively, the following indemnification agreements with each of our directors and Named Executive Officers are our only related person transactions since January 1, 2020, the following are the only transactions or series of similar transactions to which we were or will be a party in which the amount involved exceeds $120,000 and in which any director, nominee for director, executive officer, beneficial holder of more than 5% of our capital stock, or any member of their immediate family, or any entity affiliated with any of the foregoing persons had or will have a direct or indirect material interest.

2022.

Indemnification Agreements

We have entered into indemnification agreements with each of our directors and Named Executive Officers. The indemnification agreements and our amended and restated bylaws require us to indemnify our directors to the fullest extent not prohibited by Delaware law.the DGCL. Subject to certain limitations, our amended and restated bylaws also require us to advance expenses incurred by our directors and officers. For more information regarding these agreements, see the section titled “Limitations on Liability and Indemnification Matters.”

Review, Approval, or Ratification of Transactions with Related Parties

Our related party transactions policy requires that anyboard of directors has adopted a written related party transaction policy that must be reported under applicable rulessets forth policies and procedures for the review and approval or ratification of related person transactions. These policies and procedures are designed to minimize potential conflicts of interest arising from any dealings we may have with our related persons and to provide appropriate procedures for the SEC must be reviewed and approveddisclosure of any real or ratified by ourpotential conflicts of interest that may exist from time to time. Specifically, the audit committee has the responsibility to review related person transactions, unless the related partyperson is, or is associated with, a member of that committee, in which event the transaction must be reviewed and approved by our nominating and governance committee.

The audit committee (or nominating and governance committee, if applicable), in approving or rejecting the proposed transaction, may consider the relevant and available facts and circumstances, including the terms of the transaction and the impact on a director’s independence in the event the related person is a director or immediate family member or affiliate of a director.
82 
86 2023 Proxy Statement graphic


REPORT

TABLE OF THE AUDIT, RISK AND COMPLIANCE COMMITTEECONTENTS

Report of the Audit, Risk and Compliance Committee
The information contained in the following report of our audit committee is not considered to be “soliciting material,” “filed,” or incorporated by reference in any past or future filing by us under the Exchange Act or the Securities Act unless and only to the extent that we specifically incorporate it by reference.

This report is submitted by the audit committee of our board of directors. The audit committee consists of the three directors whose names appear below. Each member of the audit committee is independent under the current Nasdaq listing standards and SEC rules and regulations. Each member of the audit committee is financially literate as required by the current Nasdaq listing standards.

The principal purpose of the audit committee is to assist the board of directors in its general oversight of our accounting practices, system of internal controls, audit processes, and financial reporting processes. The audit committee also assists the board of directors in fulfilling its oversight responsibilities with respect to legal and regulatory compliance and, among other things, assists the board of directors in fulfilling its oversight responsibilities with respect to risk management, including cybersecurity, data privacy and security, legal, and compliance risks. The audit committee is responsible for appointing and retaining our independent registered public accounting firm and approving the audit and non-audit services to be provided by the independent registered public accounting firm. The audit committee’s function is more fully described in its charter.

Our audit committee has reviewed and discussed with our management and PricewaterhouseCoopers LLP our audited consolidated financial statements for the year ended December 31, 2020.2022. Our audit committee has also discussed with PricewaterhouseCoopers LLP the matters required to be discussed by the applicable requirements of the Public Company Accounting Oversight Board (United States) and the SEC.

Our audit committee has received and reviewed the written disclosures and the letter from PricewaterhouseCoopers LLP required by applicable requirements of the Public Company Accounting Oversight Board regarding the independent accountant’s communications with our audit committee concerning independence and has discussed with PricewaterhouseCoopers LLP its independence from us.

Based on the review and discussions referred to above, our audit committee recommended to our board of directors that the audited consolidated financial statements be included in our Annual Report on Form 10-K for the year ended December 31, 2020,2022, for filing with the SEC.

Submitted by the Audit, Risk and Compliance Committee


Elizabeth Nelson, Chair


Gregory C. Gretsch


Leela Srinivasan

83 
graphic2023 Proxy Statement 87


ADDITIONAL INFORMATION

TABLE OF CONTENTS

Stockholder ProposalsFrequently Asked Questions
Proxy Materials
1.
Why did I receive these proxy materials?
We have made these materials available to Be Presentedyou or, if requested, delivered paper copies by mail in connection with the Annual Meeting, which will be held exclusively online via live webcast on Friday, June 9, 2023, at 8:00 a.m. Pacific Time. As a stockholder, you are invited to participate in the Annual Meeting via live webcast and vote on the business items described in this Proxy Statement. This Proxy Statement includes information that we are required to provide to you under SEC rules and is intended to assist you in voting your shares.
2.
What is included in the proxy materials?
The proxy materials include:
The Notice of Annual Meeting of Stockholders, which we refer to as the Notice;
Our Proxy Statement for the Annual Meeting; and
Our Annual Report on Form 10-K for the year ended December 31, 2022.
If you received a paper copy of these materials by mail, the proxy materials also include a proxy card, or a voting instruction form for the Annual Meeting. If you received a “Notice of Internet Availability of Proxy Materials” (described below) instead of a paper copy of the proxy materials, see the section titled “Voting Information” below for information regarding how you can vote your shares.
3.
What does it mean if I receive more than one Notice, proxy card, or voting instruction form?
It generally means that some of your shares are registered differently or are in more than one account. Please follow the instructions included on each proxy card and vote each proxy card by telephone, through the internet, or by mail. If you requested or received paper proxy materials and you intend to vote by mail, please complete, sign, and return each proxy card you received to ensure that all of your shares are voted.
4.
Why did I receive a Notice of Internet Availability of Proxy Materials instead of a full set of proxy materials?
In accordance with SEC rules, we are using the internet as our primary means of furnishing proxy materials to our stockholders. Consequently, most stockholders will not receive paper copies of our proxy materials. We will instead send these stockholders a Notice of Internet Availability of Proxy Materials with instructions for accessing the proxy materials, including our Proxy Statement and annual report to stockholders, and voting via the internet. The Notice of Internet Availability of Proxy Materials also provides information on how stockholders may obtain paper copies of our proxy materials if they so choose. We believe this means of delivery makes the proxy distribution process more efficient and less costly and helps conserve natural resources.
We encourage you to help us conserve natural resources, as well as significantly reduce printing and mailing costs, by signing up to receive your stockholder communications electronically via email. With electronic delivery, you will be notified via email as soon as future annual reports to stockholders and proxy statements are available on the internet, and you can submit your votes online. Electronic delivery can also eliminate duplicate mailings and reduce the amount of bulky paper documents you maintain in your personal files. To sign up for electronic delivery:
If you are a registered owner (meaning you hold our common stock in your own name through our transfer agent, Computershare Trust Company, N.A., or you are in possession of stock certificates): visit www.us.computershare.com/investor and log into your account to enroll.
88 2023 Proxy Statement graphic

TABLE OF CONTENTS

If you are a beneficial owner (meaning your shares are held by a brokerage firm, a bank, a trustee, or a nominee): please follow the instructions provided to you by your broker, bank, trustee, or nominee.
Your electronic delivery enrollment will be effective until you cancel it. Stockholders who are record owners of shares of our common stock may call Computershare Trust Company, N.A., our transfer agent, at (800) 736-3001 or visit www.us.computershare.com/investor with questions about electronic delivery.
5.
How can I access the proxy materials over the internet?
The Notice, proxy card, or voting instruction form will contain instructions on how to:
View our proxy materials for the Annual Meeting on the internet; and
Instruct us to send our future proxy materials to you electronically by email.
The Notice, proxy card, or voting instruction form will contain instructions on how you may request access to proxy materials electronically on an ongoing basis. Instead of receiving future copies of our proxy statements and annual reports by mail, stockholders of record and most beneficial owners may elect to receive an email that will provide an electronic link to these documents. Choosing to receive your proxy materials electronically helps us to conserve natural resources and reduces the cost of printing and distributing our proxy materials. If you choose to access future proxy materials electronically, you will receive an email with instructions containing a link to the website where those materials are available and a link to the proxy voting website. Your election to receive future proxy materials by email will remain in effect until you revoke it.
6.
How may I obtain a paper copy of the proxy materials?
If you receive a paper Notice instead of a paper copy of the proxy materials, the Notice will provide instructions about how to obtain a paper copy of the proxy materials. If you receive the Notice by email, the email will also include instructions about how to obtain a paper copy of the proxy materials. All stockholders of record who do not receive a paper Notice or email will receive a paper copy of the proxy materials by mail.
7.
I share an address with another stockholder, and we received only one paper copy of the proxy materials or Notice. How may I obtain an additional copy?
The SEC has adopted rules that permit companies and intermediaries (such as brokers) to implement a delivery procedure called “householding.” Under this procedure, multiple stockholders who reside at the Nextsame address may receive a single copy of our annual report to stockholders and other proxy materials, including the Notice of Internet Availability, unless the affected stockholder has provided contrary instructions. This procedure reduces printing costs and postage fees and helps conserve natural resources.
This year, a number of brokers with account holders who are our stockholders will be householding our annual report to stockholders and other proxy materials, including the Notice of Internet Availability. A single Notice of Internet Availability and, if applicable, a single set of our annual report to stockholders and other proxy materials will be delivered to multiple stockholders sharing an address unless contrary instructions have been received from the affected stockholders. Once you have received notice from your broker that it will be householding communications to your address, householding will continue until you are notified otherwise or until you revoke your consent. Stockholders may revoke their consent at any time by calling Broadridge at (866) 540-7095 or writing to Broadridge, Householding Department, 51 Mercedes Way, Edgewood, NY 11717.
Upon written or oral request, we will promptly deliver a separate copy of the Notice of Internet Availability and, if applicable, our annual report to stockholders and other proxy materials to any stockholder at a shared address to which a single copy of any of those documents was delivered. To receive a separate copy of the Notice of Internet Availability and, if applicable, annual report to stockholders and other proxy materials, you may contact our Investor Relations department at our mailing address, which is 655 Montgomery Street, Suite 490, Department 17022, San Francisco, CA 94111-2676, Attn: Investor Relations, telephone number (650) 316-7500.
graphic2023 Proxy Statement 89

TABLE OF CONTENTS

8.
I share an address with another stockholder, and we received more than one paper copy of the proxy materials or the Notice. How do we obtain a single copy in the future?
Any stockholders who share the same address and receive multiple copies of our Notice of Internet Availability or annual report to stockholders and other proxy materials who wish to receive only one copy in the future can contact their bank, broker, or other holder of record to request information about householding or our Investor Relations department at our mailing address, which is 655 Montgomery Street, Suite 490, Department 17022, San Francisco, CA 94111-2676, Attn: Investor Relations, telephone number (650) 316-7500.
Voting Information
9.
Which proposals will be voted on at the Annual Meeting? How does the board of directors recommend that I vote? What is the vote required to approve each of the proposals? What effect will abstentions and broker non-votes have?
Proposal
Voting Options
Board Recommendation
Votes Required to Approve the Proposal
Effects of Abstentions
1
Election of two Class II directors named in this Proxy Statement
For, Against, or Abstain
graphicFOR
Majority of the votes cast
No effect
2
Ratification of the appointment of PricewaterhouseCoopers LLP as our independent registered public accounting firm for 2023
For, Against, or Abstain
graphicFOR
Majority of the votes cast
No effect
3
Non-binding advisory vote on Named Executive Officer compensation (Say-on-Pay)
For, Against, or Abstain
graphicFOR
Majority of the votes cast
No effect
4
Approval of Restated Certificate of Incorporation
For, Against, or Abstain
graphicFOR
Majority of voting power of outstanding shares entitled to vote
Same effect as a vote against
In deciding all matters at the Annual Meeting, as of the close of business on the Record Date, each share of common stock represents one vote.
Stockholder of Record: Shares Registered in Your Name. If, on the Record Date, your shares were registered directly in your name with our transfer agent, Computershare Trust Company, N.A., then you are considered the stockholder of record with respect to those shares. As a stockholder of record, you may vote at the Annual Meeting or vote by telephone, through the internet, or if you request or receive paper proxy materials, by filling out and returning the proxy card.
Beneficial Owner: Shares Registered in the Name of a Broker or Nominee. If, on the Record Date, your shares were held in an account with a broker, bank, trustee, or other nominee on your behalf, then you are considered the beneficial owner of shares held in “street name.” As the beneficial owner, you have the right to direct your nominee on how to vote your shares by following the voting instructions you receive. Your nominee has only limited authority to vote your shares without your instructions, as described below.
If you were a beneficial owner at the close of business on the Record Date, you may attend the Annual Meeting. You will need the 16-digit control number found on your Notice of Internet Availability of Proxy Materials, your proxy card, or the instructions that accompany your proxy materials if you wish to attend the
90 2023 Proxy Statement graphic

TABLE OF CONTENTS

Annual Meeting with the right to vote and submit a question. Even if you do not have your 16-digit control number or were not a stockholder as of the close of business on the Record Date, you can still access the meeting but will not be able to vote at the meeting or submit a question.
If your shares are held in street name, follow the voting instructions you receive from your nominee.
Broker non-votes occur when shares held by a broker for a beneficial owner are not voted because the broker did not receive voting instructions from the beneficial owner and lacked discretionary authority to vote the shares. A broker is entitled to vote shares held for a beneficial owner on “routine” matters without instructions from the beneficial owner of those shares. Absent instructions from the beneficial owner of such shares, a broker is not entitled to vote shares held for a beneficial owner on “non-routine” matters. At our Annual Meeting, only the ratification of PricewaterhouseCoopers LLP as our independent registered public accounting firm for the year ending December 31, 2023, is considered a routine matter. The proposal for the election of directors and any other proposals presented at the Annual Meeting are non-routine matters. Broker non-votes are counted for purposes of determining whether a quorum is present and have no effect on the outcome of the matters voted upon, except with respect to Proposal 4, for which a broker non-vote is counted as a vote against the proposal. Accordingly, we encourage you to provide voting instructions to your broker, whether or not you plan to attend the Annual Meeting.
Our board of directors recommends that you vote “FOR” the election of each of the Class II directors named in this Proxy Statement, which we refer to as Proposal 1, “FOR” the ratification of the appointment of PricewaterhouseCoopers LLP as our independent registered public accounting firm for the year ending December 31, 2023, which we refer to as Proposal 2, “FOR” the approval, on a non-binding advisory basis, of the compensation of our Named Executive Officers as disclosed in this Proxy Statement, which we refer to as Proposal 3, and “FOR” the approval of the Restated Certificate of Incorporation, which we refer to as Proposal 4. None of our directors or Named Executive Officers have any substantial interest in any matter to be acted upon, other than, with respect to our Named Executive Officers, Proposal 3 and Proposal 4, and, with respect to Leela Srinivasan and Gary Steele, Proposal 1.
10.
Who is entitled to vote? How many shares can I vote?
Only holders of record of our common stock at the close of business on the Record Date will be entitled to vote at the Annual Meeting. At the close of business on the Record Date, there were 133,466,746 shares of our common stock outstanding and entitled to vote. For a 10-day period ending the day before the Annual Meeting date, a complete list of the stockholders entitled to vote at the Annual Meeting will be available for examination by any stockholder for any purpose relating to the Annual Meeting during ordinary business hours at our headquarters.
You may vote all shares of our common stock that you owned as of the Record Date, including (i) shares held directly in your name as the stockholder of record, including shares purchased or acquired through our equity incentive plans, and (ii) shares held for you as the beneficial owner through a broker, bank, or other nominee.
11.
How can I vote my shares?
If you are a stockholder of record, you may:
vote via the virtual meeting website—any stockholder can attend the Annual Meeting by visiting www.virtualshareholdermeeting.com/UPWK2023, where stockholders may vote and submit questions during the meeting. The meeting starts at 8:00 a.m. Pacific Time on Friday, June 9, 2023. Please have your 16-digit control number to join the Annual Meeting. Instructions on how to attend and participate via the internet are posted at www.proxyvote.com;
vote by telephone or through the internet—in order to do so, please follow the instructions shown on the Notice of Internet Availability of Proxy Materials or your proxy card. Votes submitted by telephone or through the internet must be received by 8:59 p.m. Pacific Time on June 8, 2023; or
vote by mail—if you request or receive a paper proxy card and voting instructions by mail, simply complete, sign, and date the enclosed proxy card and promptly return it in the envelope provided or, if
graphic2023 Proxy Statement 91

TABLE OF CONTENTS

the envelope is missing, please mail your completed proxy card to Vote Processing, c/o Broadridge Financial Solutions, Inc., 51 Mercedes Way, Edgewood, New York 11717. Your signed and dated proxy card must be received prior to the Annual Meeting in order to be voted.
Submitting your proxy, whether by telephone, through the internet, or, if you request or receive a paper proxy card, by mail, will not affect your right to vote should you decide to attend the Annual Meeting. If you are not the stockholder of record, please refer to the voting instructions provided by your nominee to direct your nominee on how to vote your shares. Your vote is important. Whether or not you plan to attend the Annual Meeting, we urge you to vote by proxy to ensure that your vote is counted.
All proxies will be voted in accordance with the instructions specified. If you sign a physical proxy card and return it without instructions as to how your shares should be voted on a particular proposal at the Annual Meeting, your shares will be voted in accordance with the recommendations of our board of directors stated above.
If you do not vote and you hold your shares in street name, and your broker does not have discretionary power to vote your shares, your shares may constitute “broker non-votes” (as described above) and will not be counted in determining the number of shares necessary for approval of the proposals. However, shares that constitute broker non-votes will be counted for the purpose of establishing a quorum for the Annual Meeting.
If you receive more than one proxy card, your shares are registered in more than one name or are registered in different accounts. To make certain all of your shares are voted, please follow the instructions included on each proxy card and vote each proxy card by telephone, through the internet, or by mail. If you requested or received paper proxy materials and you intend to vote by mail, please complete, sign, and return each proxy card you received to ensure that all of your shares are voted.
12.
May I change my vote or revoke my proxy?
A stockholder of record who has given a proxy may revoke it at any time before it is exercised at the Annual Meeting by:
delivering to our Corporate Secretary by mail a written notice stating that the proxy is revoked;
signing and delivering a proxy bearing a later date;
voting again by telephone or through the internet; or
attending and voting at the Annual Meeting (although attendance at the Annual Meeting will not, by itself, revoke a proxy).
Please note, however, that if your shares are held of record by a broker, bank, or other nominee and you wish to revoke a proxy, you must contact that firm to revoke any prior voting instructions.
13.
What if I return my proxy card but do not provide voting instructions?
If you are a stockholder of record and you return your signed proxy card without giving specific voting instructions, your shares will be voted as recommended by our board of directors (see Question 9 above).
14.
What if I am a beneficial owner and do not give voting instructions to my broker?
If you are a beneficial owner of shares, your broker, bank, or other nominee is not permitted to vote on your behalf on the matters to be considered at the Annual Meeting, except for Proposal 2 (the ratification of the appointment of PricewaterhouseCoopers LLP as our independent auditor for 2023), unless you provide specific instructions by completing and returning the voting instruction form or following the instructions provided to you to vote your shares on the internet or by telephone. If you do not provide voting instructions,
92 2023 Proxy Statement graphic

TABLE OF CONTENTS

your shares will not be voted on any proposal except for Proposal 2. This is called a “broker non-vote.” For your vote to be counted, you will need to (i) communicate your voting decision to your broker, bank, or other nominee before the date of the Annual Meeting, or (ii) vote during the Annual Meeting.
15.
Is my vote confidential?
Proxy instructions, ballots, and voting tabulations that identify individual stockholders are handled in a manner designed to protect your voting privacy. Your vote will not be disclosed, either within our company or to third parties, except: (i) as necessary to meet applicable legal requirements; (ii) to allow for the tabulation of votes and certification of the vote; and (iii) to facilitate proxy solicitation. To the extent that stockholders provide written comments on their proxy cards, those comments will be forwarded to management.
16.
What constitutes a quorum?
The holders of a majority of the voting power of the shares of our common stock issued and outstanding and entitled to vote at the Annual Meeting as of the Record Date must be present at the Annual Meeting in order to hold the Annual Meeting and conduct business. This presence is called a quorum. Your shares are counted as present at the Annual Meeting if you are present and vote at the Annual Meeting or if you have properly submitted a proxy.
17.
Who will bear the cost of soliciting votes for the Annual Meeting?
The accompanying proxy is solicited by our board of directors on behalf of Upwork Inc. We have retained D.F. King & Co., Inc. to assist us with the solicitation of proxies, for which we will pay an aggregate fee of $15,000, plus reasonable and documented costs and expenses. We will pay the expenses of soliciting proxies, including preparation, assembly, printing, and mailing of this Proxy Statement, the proxy card, and any other information furnished to stockholders. Following the original mailing of the soliciting materials, we and our agents, including directors, officers, and other employees, without additional compensation, may solicit proxies by mail, email, telephone, facsimile, or other similar means. Following the original mailing of the soliciting materials, we will request brokers, custodians, nominees, and other record holders to forward copies of the soliciting materials to persons for whom they hold shares and to request authority for the exercise of proxies. In such cases, we, upon the request of the record holders, will reimburse such holders for their reasonable expenses. If you choose to access the proxy materials or vote through the internet, you are responsible for any internet access charges you may incur.
18.
What happens if additional matters are presented at the Annual Meeting?
Other than the four items of business described in this Proxy Statement, we are not aware of any other business to be acted upon at the Annual Meeting. If you grant a proxy, the persons named as proxy holders will have the discretion to vote your shares on any additional matters properly presented for a vote at the Annual Meeting. If, for any reason, any of the nominees is not available as a candidate for director, the persons named as proxy holders will vote your proxy for such other candidate or candidates as may be nominated by our board of directors.
19.
Where can I find the voting results of the Annual Meeting?
Voting results will be tabulated and certified by the inspector of elections appointed for the Annual Meeting. The preliminary voting results will be announced at the Annual Meeting. The final results will be tallied by the inspector of elections and filed with the SEC in a current report on Form 8-K within four business days of the Annual Meeting. The Form 8-K can be found at www.sec.gov and in the “Investor Relations” section of our website.
graphic2023 Proxy Statement 93

TABLE OF CONTENTS

Attending the Annual Meeting
20.
How can I attend the Annual Meeting?
The Annual Meeting will be a completely virtual meeting of stockholders, which will be conducted exclusively online via live webcast. You are entitled to attend and participate in the Annual Meeting only if you were a stockholder as of the close of business on the Record Date, or if you hold a valid proxy for the Annual Meeting.
You will be able to attend the Annual Meeting online and submit your questions during the meeting by visiting www.virtualshareholdermeeting.com/UPWK2023. You also will be able to vote your shares by attending the Annual Meeting online. To participate in the Annual Meeting, you will need the 16-digit control number included on your Notice, on your proxy card (if you requested printed materials), or on the instructions that accompanied your proxy materials. Stockholders will need the 16-digit control number to submit a question.
The online meeting will begin promptly at 8:00 a.m. Pacific Time on Friday, June 9, 2023. We encourage you to access the meeting prior to the start time. Online check-in will begin at 7:45 a.m. Pacific Time, and you should allow sufficient time for the check-in procedures.
21.
What if during the check-in time or during the meeting I have technical difficulties or trouble accessing the virtual meeting website?
If we experience technical difficulties during the meeting (e.g., a temporary or prolonged power outage), we will determine whether the meeting can be promptly reconvened (if the technical difficulty is temporary) or whether the meeting will need to be reconvened on a later day (if the technical difficulty is more prolonged). In any situation, we will promptly notify stockholders of the decision via www.virtualshareholdermeeting.com/UPWK2023. If you encounter technical difficulties accessing our meeting or asking questions during the meeting, a support line will be available on the login page of the virtual meeting website.
22.
Why are you holding a virtual meeting instead of a physical meeting?
We have conducted efficient and effective virtual meetings since 2019. We intend to continue to ensure that our stockholders are afforded the same rights and opportunities to participate virtually as they would at an in-person meeting. We believe the virtual format makes it easier for stockholders to attend and participate fully and equally in the Annual Meeting. Our virtual meeting format helps us engage with all stockholders regardless of size, resources, or physical location, saves us and stockholders time and money, and reduces our environmental impact.
23.
Can stockholders ask questions during the Annual Meeting?
Yes. If you wish to submit a question during the Annual Meeting, log into the virtual meeting platform at www.virtualshareholdermeeting.com/UPWK2023, type your question into the “Ask a Question” field, and click “Submit.” If your question is properly submitted during the relevant portion of the meeting agenda, we will respond to your question during the live webcast, subject to time constraints. Questions that are substantially similar may be grouped and answered together to avoid repetition. We reserve the right to exclude questions that are, among other things, irrelevant to the business of the Annual Meeting, irrelevant to our business, related to material nonpublic information about our company, derogatory or in bad taste, in furtherance of the stockholder’s personal or business interests, related to pending or threatened litigation, repetitious or already made by another stockholder, related to personal matters or grievances, or out of order or otherwise not suitable for the conduct of the Annual Meeting (as determined by the chairperson of the Annual Meeting or our Corporate Secretary in their sole judgment). A webcast replay of the Annual Meeting, including the Q&A session, will be available for 90 days following the Annual Meeting at www.virtualshareholdermeeting.com/UPWK2023.
94 2023 Proxy Statement graphic

TABLE OF CONTENTS

24.
What is the deadline to propose actions for consideration at the 2024 annual meeting of stockholders or to nominate individuals to serve as directors?
Our amended and restated bylaws provide that, for stockholder nominations to our board of directors or other proposals to be considered at an annual meeting, the stockholder must give timely notice thereof in writing to the attention of the Corporate Secretary at our principal executive offices, the address of which is currently Upwork Inc., 475 Brannan Street, Suite 430, San Francisco, California 95054.

To be timely for our 20222024 annual meeting of stockholders a stockholder’s notice must be delivered to or mailed and received by our Corporate Secretary at our principal executive offices not earlier than 5:2:00 p.m. EasternPacific Time on February 1, 202210, 2024, and not later than 5:2:00 p.m. EasternPacific Time on March 3, 2022.11, 2024. A stockholder’s notice to the Corporate Secretary must set forth as to each matter the stockholder proposes to bring before the annual meeting the information required by our amended and restated bylaws.

Additionally, our amended and restated bylaws permit a stockholder, or a group of up to 20 stockholders, owning at least 3% of our outstanding common stock continuously for at least three years to nominate and include in our proxy materials for director nominees constituting up to the greater of two individuals or 20% of our board of directors, subject to reduction in certain circumstances, and subject to the stockholders and the nominees satisfying the requirements specified in our amended and restated bylaws. Our obligation to include director nominees in our annual meeting proxy materials is also subject to certain exceptions as set forth in our amended and restated bylaws. Written notice of the nomination(s) for our 20222024 annual meeting of stockholders must be submitted to the attention of the Corporate Secretary at our principal executive offices, the address of which currently is Upwork Inc., 475 Brannan Street, Suite 430, San Francisco, California 95054, no earlier than 5:2:00 p.m. EasternPacific Time on November 21, 2021,30, 2023, and no later than 5:2:00 p.m. EasternPacific Time on December 21, 2021,30, 2023, subject to certain exceptions as set forth in our amended and restated bylaws.

In addition, to comply with the universal proxy rules, stockholders who intend to solicit proxies in support of director nominees other than Upwork nominees must provide notice that sets forth the information required by Rule 14a-19 under the Exchange Act no later than April 10, 2024.

Stockholder proposals submitted pursuant to Rule 14a-8 under the Exchange Act and intended to be presented at our 20222024 annual meeting of stockholders must be received by us not later than December 21, 2021,30, 2023, in order to be considered for inclusion in our proxy materials for that meeting. Proposals should be sent to our Corporate Secretary at our principal executive offices, together with proof of ownership of our common stock in accordance with Rule 14a-8 under the Exchange Act. We strongly encourage any stockholder interested in submitting a proposal to contact our Corporate Secretary in advance of this deadline to discuss the proposal.

Delinquent Section 16(a)

25.
Where can I find more information about Upwork’s SEC filings, governance documents, and communicating with Upwork and the board of directors?
SEC Filings and Reports

Section 16(a) of the Exchange Act requires

Our SEC filings, including our directors, executive officers,Annual Reports on Form 10-K, Quarterly Reports on Form 10-Q, Current Reports on Form 8-K, and any persons who own more than 10%amendments to those reports, are available free of charge on our “Investor Relations” section of our common stock to file initial reports of ownership and reports of changes in ownership with the SEC. Such persons are required by SEC regulation to furnish us with copies of all Section 16(a) forms that they file. Based solely on our review of the copies of such forms furnished to us and written representations from our directors and executive officers, we believe that all Section 16(a) filing requirements were timely metwebsite, which is located at investors.upwork.com, under “SEC Filings” in the year ended December 31, 2020, except that a Form 4 was not timely filed for Thomas Layton for a pro rata distribution“Financials” section of common stock from Benchmark Founders’ Fund V, L.P., of which Mr. Layton is a limited partner, on May 19, 2020.

Annual Report

our website.

We will mail, without charge, upon written request, a copy of our annual report to stockholders,Annual Report, including the financial statements and list of exhibits, and any exhibit specifically requested. Requests should be sent to our mailing address:

84 

Upwork Inc.


655 Montgomery Street


Suite 490, Department 17022


San Francisco, CA 94111-2676


Attn: Investor Relations
graphic2023 Proxy Statement 95

TABLE OF CONTENTS

Corporate Governance Documents
Our annual report to stockholders is alsoCorporate Governance Guidelines, charters of the principal committees of our board of directors, our Code of Business Conduct and Ethics, and other key corporate governance documents and materials are available onat the “Investor Relations” section of our website, which is located at investors.upwork.com, under “SEC Filings”by clicking on “Documents & Charters” in the “Annual Reports”“Governance” section of our website, or by following the instructions in the Notice of Internet Availability of Proxy Materials.

Electronic Delivery of Stockholder Communications

We encourage you to help us conserve natural resources, as well as significantly reduce printingwebsite.

Communicating with Management and mailing costs, by signing up to receive your stockholder communications electronically via email. With electronic delivery, you will be notified via email as soon as future annual reports to stockholders and proxy statements are available on the internet, and you can submit your votes online. Electronic delivery can also eliminate duplicate mailings and reduce the amount of bulky paper documents you maintain in your personal files. To sign up for electronic delivery:

If you are a registered owner (meaning you hold our common stock in your own name through our transfer agent, Computershare Trust Company, N.A., or you are in possession of stock certificates): visit www-us.computershare.com/investor and log into your account to enroll.
If you are a beneficial owner (meaning your shares are held by a brokerage firm, a bank, a trustee, or a nominee): please follow the instructions provided to you by your broker, bank, trustee, or nominee.

Your electronic delivery enrollment will be effective until you cancel it. Stockholders who are record owners of shares of our common stock may call Computershare Trust Company, N.A., our transfer agent, at (800) 736-3001 or visit www-us.computershare.com/investor with questions about electronic delivery.

“Householding”—Stockholders Sharing the Same Last Name and Address

The SEC has adopted rules that permit companies and intermediaries (such as brokers) to implement a delivery procedure called “householding.” Under this procedure, multiple stockholders who reside at the same address may receive a single copy of our annual report to stockholders and other proxy materials, including the Notice of Internet Availability, unless the affected stockholder has provided contrary instructions. This procedure reduces printing costs and postage fees, and helps in conserving natural resources.

This year, a number of brokers with account holders who are our stockholders will be “householding” our annual report to stockholders and other proxy materials, including the Notice of Internet Availability. A single Notice of Internet Availability and, if applicable, a single set of our annual report to stockholders and other proxy materials will be delivered to multiple stockholders sharing an address unless contrary instructions have been received from the affected stockholders. Once you have received notice from your broker that it will be “householding” communications to your address, “householding” will continue until you are notified otherwise or until you revoke your consent. Investor Relations

Stockholders may revoke their consent at any time by calling Broadridge at (866) 540-7095contact management or writing to Broadridge, Householding Department, 51 Mercedes Way, Edgewood, NY, 11717.

85 

Upon written or oral request, we will promptly deliver a separate copy of the Notice of Internet Availability and, if applicable, our annual report to stockholders and other proxy materials to any stockholder at a shared address to which a single copy of any of those documents was delivered. To receive a separate copy of the Notice of Internet Availability and, if applicable, annual report to stockholders and other proxy materials, you may contact our Investor Relations departmentin writing at our mailing address, which is 655 Montgomery Street, Suite 490, Department 17022, San Francisco, CA 94111-2676, Attn: Investor Relations, telephone number (650) 316-7500.

Any stockholders who share316-7500, or by email at investor@upwork.com.

Communicating with the same addressBoard of Directors
Stockholders and receive multiple copies of our Notice of Internet Availability or annual report to stockholders and other proxy materialsinterested parties who wish to receive only one copy incommunicate with our board of directors, non-management members of our board of directors as a group, a committee of our board of directors, or a specific member of our board of directors (including our chairperson) may do so by letters addressed to the future can contact their bank, broker,attention of our Corporate Secretary.
All communications are reviewed by the Corporate Secretary and provided to the members of our board of directors as appropriate. Sales materials, abusive, threatening, or other holderotherwise inappropriate materials, and items unrelated to the duties and responsibilities of recordour board of directors will not be provided to request information about householding or our Investor Relations department at thedirectors.
The mailing address or telephone number listed above.

for these communications is:
Upwork Inc.
c/o Corporate Secretary
655 Montgomery Street, Suite 490, Department 17022
San Francisco, CA 94111-2676
86 
96 2023 Proxy Statement graphic


OTHER MATTERS

TABLE OF CONTENTS

Other Matters
Our board of directors does not presently intend to bring any other business before the Annual Meeting, and so far as is known to our board of directors, no matters are to be brought before the Annual Meeting except as specified in the Notice of Annual Meeting of Stockholders. As to any business that may arise and properly come before the Annual Meeting, however, it is intended that proxies, in the form enclosed, will be voted in respect thereof in accordance with the judgment of the persons voting such proxies.

By Order of the Board of Directors,
graphic
Hayden Brown

President and Chief Executive Officer
87 
graphic2023 Proxy Statement 97

TABLE OF CONTENTS

Appendix A-1: Restated Certificate of Incorporation

* * * * * * * * * * *
UPWORK INC. 655 MONTGOMERY STREET, SUITE 490 DEPARTMENT 17022 SAN FRANCISCO, CA 94111-2676 VOTE BY INTERNET Before

RESTATED CERTIFICATE OF INCORPORATION
ARTICLE I: NAME
The Meeting - Go to www.proxyvote.com Usename of the Internet to transmit your voting instructions and for electronic deliverycorporation is Upwork Inc. (the “Corporation”).
ARTICLE II: AGENT FOR SERVICE OF PROCESS
The address of information. Vote by 11:59 P.M. ET on May 31, 2021. Have your proxy card in hand when you access the web site and follow the instructions to obtain your records and to create an electronic voting instruction form. During The Meeting - Go to www.virtualshareholdermeeting.com/UPWK2021 You may attend the meeting via the Internet and vote during the meeting. Have the information that is printedCorporation’s registered office in the box marked byState of Delaware is 9 E. Loockerman Street, Suite 311, Dover, DE, 19901, Kent County. The name of the arrow availableregistered agent of the Corporation at that address is Registered Agent Solutions, Inc.
ARTICLE III: PURPOSE
The purpose of the Corporation is to engage in any lawful act or activity for which corporations may be organized under the General Corporation Law of the State of Delaware (the “General Corporation Law”).
ARTICLE IV: AUTHORIZED STOCK
1. Total Authorized. The total number of shares of all classes of stock that the Corporation has authority to issue is five hundred million (500,000,000) shares, consisting of two classes: four hundred and follow the instructions. VOTE BY PHONE - 1-800-690-6903 Use any touch-tone telephone to transmit your voting instructions. Vote by 11:59 P.M. ET on May 31, 2021. Have your proxy card in hand when you callninety million (490,000,000) shares of Common Stock, $0.0001 par value per share (“Common Stock”), and then follow the instructions. VOTE BY MAIL Mark, sign and date your proxy card and return it in the postage-paid envelope we have provided or return it to Vote Processing, c/o Broadridge, 51 Mercedes Way, Edgewood, NY 11717. Your signed and dated proxy card must be received prior to the Annual Meeting in order to be voted. TO VOTE, MARK BLOCKS BELOW IN BLUE OR BLACK INK AS FOLLOWS TO VOTE, MARK BLOCKS BELOW IN BLUE OR BLACK INK AS FOLLOWS D37216-P49965 KEEP THIS PORTION FOR YOUR RECORDS THIS PROXY CARD IS VALID ONLY WHEN SIGNED AND DATED. DETACH AND RETURN THIS PORTION ONLY UPWORK INC.ten million (10,000,000) shares of Preferred Stock, $0.0001 par value per share (“Preferred Stock”).
2. Designation of Additional Series.
2.1. The Board of Directors recommends youof the Corporation (the “Board”) is authorized, subject to any limitations prescribed by the law of the State of Delaware, to provide for the issuance of the shares of Preferred Stock in one or more series, and, by filing a Certificate of Designation pursuant to the applicable law of the State of Delaware (“Certificate of Designation”), to establish from time to time the number of shares to be included in each such series, to fix the designation, powers (including voting powers), preferences and relative, participating, optional or other special rights, if any, of the shares of each such series and any qualifications, limitations or restrictions thereof, and, except where otherwise provided in the applicable Certificate of Designation, to thereafter increase (but not above the total number of authorized shares of the Preferred Stock) or decrease (but not below the number of shares of such series then outstanding) the number of shares of any such series. The number of authorized shares of Preferred Stock may also be increased or decreased (but not below the number of shares thereof then outstanding) by the affirmative vote FORof the following: holders of two-thirds of the voting power of all of the then-outstanding shares of capital stock of the Corporation entitled to vote thereon, without a separate vote of the holders of the Preferred Stock, irrespective of the provisions of Section 242(b)(2) of the General Corporation Law, unless a separate vote of the holders of one or more series is required pursuant to the terms of any Certificate of Designation; provided, however, that if two-thirds of the Whole Board (as defined below) has approved such increase or decrease of the number of authorized shares of Preferred Stock, then only the affirmative vote of the holders of a majority of the voting power of all of the then-outstanding shares of the capital stock of the Corporation entitled to vote generally in the election of directors, voting together as a single class, without a separate vote of the holders of the Preferred Stock (unless a separate vote of the holders of one or more series is required pursuant to the terms of any Certificate of Designation), shall be required to effect such increase or decrease. For purposes of this Restated Certificate of Incorporation (as the same may be amended and/or restated from time to time, including pursuant the terms of any Certificate of Designation designating a series of Preferred Stock, this “Certificate of Incorporation”), the term “Whole Board” shall mean the total number of authorized directors whether or not there exist any vacancies in previously authorized directorships.
graphic2023 Proxy Statement A-1-1

TABLE OF CONTENTS

2.2 Except as otherwise expressly provided in any Certificate of Designation designating any series of Preferred Stock pursuant to the foregoing provisions of this Article IV, any new series of Preferred Stock may be designated, fixed and determined as provided herein by the Board without approval of the holders of Common Stock or the holders of Preferred Stock, or any series thereof, and any such new series may have powers, preferences and rights, including, without limitation, voting powers, dividend rights, liquidation rights, redemption rights and conversion rights, senior to, junior to or pari passu with the rights of the Common Stock, any series of Preferred Stock or any future class or series of capital stock of the Corporation.
2.3 Each outstanding share of Common Stock shall entitle the holder thereof to one vote on each matter properly submitted to the stockholders of the Corporation for their vote; provided, however, that, except as otherwise required by law, holders of Common Stock shall not be entitled to vote on any amendment to this Certificate of Incorporation that relates solely to the terms of one or more outstanding series of Preferred Stock if the holders of such affected series are entitled, either separately or together as a class with the holders of one or more other such series, to vote thereon pursuant to this Certificate of Incorporation.
ARTICLE V: AMENDMENT OF BYLAWS
The Board shall have the power to adopt, amend or repeal the Bylaws of the Corporation (as the same may be amended and/or restated from time to time, the “Bylaws”). Any adoption, amendment or repeal of the Bylaws by the Board shall require the approval of a majority of the Whole Board. The stockholders shall also have power to adopt, amend or repeal the Bylaws; provided, however, that notwithstanding any other provision of this Certificate of Incorporation or any provision of law that might otherwise permit a lesser or no vote, but in addition to any vote of the holders of any class or series of stock of the Corporation required by applicable law or by this Certificate of Incorporation, the affirmative vote of the holders of at least two-thirds of the voting power of all of the then-outstanding shares of the capital stock of the Corporation entitled to vote generally in the election of directors, voting together as a single class, shall be required for the stockholders to adopt, amend or repeal any provision of the Bylaws; provided further, that, in the case of any proposed adoption, amendment or repeal of any provisions of the Bylaws that is approved by the Board and submitted to the stockholders for adoption thereby, if two-thirds of the Whole Board has approved such adoption, amendment or repeal of any provisions of the Bylaws, then only the affirmative vote of the holders of a majority of the voting power of all of the then-outstanding shares of the capital stock of the Corporation entitled to vote generally in the election of directors, voting together as a single class, shall be required to adopt, amend or repeal any provision of the Bylaws.
ARTICLE VI: MATTERS RELATING TO THE BOARD OF DIRECTORS
1. ElectDirector Powers. Except as otherwise provided by the General Corporation Law or this Certificate of Incorporation, the business and affairs of the Corporation shall be managed by or under the direction of the Board.
2. Number of Directors. Subject to the special rights of the holders of any series of Preferred Stock to elect additional directors under specified circumstances, the total number of directors constituting the Whole Board shall be fixed from time to time exclusively by resolution adopted by a majority of the Whole Board.
3. Classified Board. Subject to the special rights of the holders of one or more series of Preferred Stock to elect additional directors under specified circumstances, the directors shall be divided, with respect to the time for which they severally hold office, into three classes designated as Class I, Class II and Class III, respectively (the “Classified Board”). The Board may assign members of the Board already in office to the Classified Board. The number of directors in each class shall be as nearly equal as is practicable. The initial term of office of the Class I directors shall expire at the Corporation’s first annual meeting of stockholders following the closing of the Corporation’s initial public offering pursuant to an effective registration statement under the Securities Act of 1933, as amended, relating to the offer and sale of Common Stock to the public (the “Initial Public Offering”), the initial term of office of the Class II directors shall expire at the Corporation’s second annual meeting of stockholders following the closing of the Initial Public Offering and the initial term of office of the Class III directors shall expire at the Corporation’s third annual meeting of stockholders following the closing of the Initial Public Offering. At each annual meeting of stockholders following the closing of the Initial Public Offering, directors elected to servesucceed those directors of the class whose terms then expire shall be elected for a three-yearterm of office expiring at the third succeeding annual meeting of stockholders after their election.
A-1-2 2023 Proxy Statement graphic

TABLE OF CONTENTS

4. Term and Removal. Each director shall hold office until the annual meeting at which such director’s term expires and until such director’s successor is duly elected and qualified, or until such director’s earlier death, resignation, disqualification or removal. Any director may resign by delivering a resignation in writing or by electronic transmission to the Corporation at its principal office or to the Chairperson of the Board, the Chief Executive Officer, or the Secretary. Subject to the special rights of the holders of any series of Preferred Stock, no director may be removed from the Board except for cause and only by the affirmative vote of the holders of at least two-thirds of the voting power of the then-outstanding shares of capital stock of the Corporation entitled to vote thereon, voting together as a single class. In the event of any increase or decrease in the authorized number of directors, (a) each director then serving as such shall nevertheless continue as a director of the class of which he or she is a member and (b) the newly created or eliminated directorships resulting from such increase or decrease shall be apportioned by the Board among the classes of directors so as to make all classes as nearly equal in number as is practicable, provided that no decrease in the number of directors constituting the Board shall shorten the term of any director.
5. Board Vacancies and Newly Created Directorships. Subject to the special rights of the holders of any series of Preferred Stock, any vacancy occurring in the Board for any cause, and any newly created directorship resulting from any increase in the authorized number of directors, shall be filled only by the affirmative vote of a majority of the directors then in office, even if less than a quorum, or by a sole remaining director, and shall not be filled by the stockholders. Any director elected in accordance with the preceding sentence shall hold office for a term expiring at the 2024 Annual Meetingannual meeting of stockholders at which the term of office of the class to which the director has been assigned expires and until such director'sdirector’s successor isshall have been duly elected and qualified. Nominees: 01) Hayden Brown 02) Gregory C. Gretsch 03) Anilu Vazquez-Ubarriqualified, or until such director’s earlier death, resignation, disqualification or removal.
6. Vote by Ballot. Election of directors need not be by written ballot unless the Bylaws shall so provide.
7. Preferred Directors. If and for so long as the holders of any series of Preferred Stock have the special right to elect additional directors, then upon commencement and for the duration of the period during which such right continues: (i) the then otherwise total authorized number of directors of the Corporation shall automatically be increased by such specified number of directors, and the holders of such Preferred Stock shall be entitled to elect the additional directors so provided for or fixed pursuant to said provisions, and (ii) each such additional director shall serve until such director’s successor shall have been duly elected and qualified, or until such director’s right to hold such office terminates pursuant to said provisions, whichever occurs earlier, subject to his or her earlier death, resignation, retirement, disqualification or removal. Except as otherwise provided by the Board in the resolution or resolutions establishing such series, whenever the holders of any series of Preferred Stock having such right to elect additional directors are divested of such right pursuant to the provisions of such stock, the terms of office of all such additional directors elected by the holders of such stock, or elected to fill any vacancies resulting from the death, resignation, disqualification or removal of such additional directors, shall forthwith terminate and the total authorized number of directors of the Corporation shall be reduced accordingly.
ARTICLE VII: DIRECTOR AND OFFICER LIABILITY
1. Limitation of Liability. To the fullest extent permitted by law, neither a director nor an officer of the Corporation shall be personally liable to the Corporation or its stockholders for monetary damages for breach of fiduciary duty as a director or officer, as applicable. Without limiting the effect of the preceding sentence, if the General Corporation Law is hereafter amended to authorize the further elimination or limitation of the liability of a director or officer, then the liability of a director or officer of the Corporation shall be eliminated or limited to the fullest extent permitted by the General Corporation Law, as so amended.
2. Change in Rights. Neither any amendment nor repeal of this Article VII, nor the adoption of any provision of this Certificate of Incorporation inconsistent with this Article VII, shall eliminate, reduce or otherwise adversely affect any limitation on the personal liability of a director or officer of the Corporation existing hereunder with respect to any act or omission occurring prior to such amendment, modification or repeal.
ARTICLE VIII: MATTERS RELATING TO STOCKHOLDERS
1. No Action by Written Consent of Stockholders. Subject to the rights of any series of Preferred Stock then outstanding, no action shall be taken by the stockholders of the Corporation except at a duly called annual or special meeting of stockholders and no action shall be taken by the stockholders of the Corporation by written consent in lieu of a meeting.
graphic2023 Proxy Statement A-1-3

TABLE OF CONTENTS

2. Special Meeting of Stockholders. Special meetings of the stockholders of the Corporation may be called only by the Chairperson of the Board, the Chief Executive Officer, the Lead Independent Director (as defined in the Bylaws), the President, or the Board acting pursuant to a resolution adopted by a majority of the Whole Board and may not be called by the stockholders or any other person or persons.
3. Advance Notice of Stockholder Nominations and Business Transacted at Special Meetings. Advance notice of stockholder nominations for the election of directors of the Corporation and of business to be brought by stockholders before any meeting of stockholders of the Corporation shall be given in the manner provided in the Bylaws. Business transacted at special meetings of stockholders shall be limited to the purpose or purposes stated in the notice of meeting.
ARTICLE IX: CHOICE OF FORUM
Unless the Corporation consents in writing to the selection of an alternative forum, the Court of Chancery of the State of Delaware (or if the Court of Chancery does not have jurisdiction, the federal district court for the District of Delaware), to the fullest extent permitted by law, shall be the sole and exclusive forum for: (a) any derivative action or proceeding brought on behalf of the Corporation; (b) any action asserting a claim of breach of a fiduciary duty owed by, or other wrongdoing by, any director, officer, stockholder, employee or agent of the Corporation to the Corporation or the Corporation’s stockholders; (c) any action asserting a claim against the Corporation arising pursuant to any provision of the General Corporation Law, this Certificate of Incorporation or the Bylaws or as to which the General Corporation Law confers jurisdiction on the Court of Chancery of the State of Delaware; (d) any action to interpret, apply, enforce or determine the validity of this Certificate of Incorporation or the Bylaws; (e) any action asserting a claim against the Corporation governed by the internal affairs doctrine; or (f) any action asserting an “internal corporate claim” as that term is defined in Section 115 of the General Corporation Law.
Any person or entity purchasing or otherwise acquiring or holding any interest in shares of capital stock of the Corporation shall be deemed to have notice of and to have consented to the provisions of this Article IX. Failure to enforce the foregoing provisions of this Article IX would cause the Corporation irreparable harm, and the Corporation shall be entitled to equitable relief, including injunctive relief and specific performance, to enforce the foregoing provisions.
ARTICLE X: AMENDMENT OF CERTIFICATE OF INCORPORATION
If any provision of this Certificate of Incorporation shall be held to be invalid, illegal, or unenforceable, then such provision shall nonetheless be enforced to the maximum extent possible consistent with such holding and the remaining provisions of this Certificate of Incorporation (including without limitation, all portions of any section of this Certificate of Incorporation containing any such provision held to be invalid, illegal, or unenforceable, which is not invalid, illegal, or unenforceable) shall remain in full force and effect.
The Corporation reserves the right to amend or repeal any provision contained in this Certificate of Incorporation in the manner prescribed by the laws of the State of Delaware and all rights conferred upon stockholders are granted subject to this reservation; provided, however, that, notwithstanding any provision of this Certificate of Incorporation or any provision of law that might otherwise permit a lesser vote or no vote (but subject to Section 2 of Article IV hereof), but in addition to any vote of the holders of any class or series of the stock of the Corporation required by law or by this Certificate of Incorporation, the affirmative vote of the holders of at least two-thirds of the voting power of all of the then-outstanding shares of the capital stock of the Corporation entitled to vote generally in the election of directors, voting together as a single class, shall be required to amend or repeal any provision of this Certificate of Incorporation; provided, further, that if two-thirds of the Whole Board has approved such amendment or repeal of any provisions of this Certificate of Incorporation, then only the affirmative vote of the holders of at least a majority of the voting power of all of the then-outstanding shares of capital stock of the Corporation entitled to vote generally in the election of directors, voting together as a single class (in addition to any other vote of the holders of any class or series of stock of the Corporation required by law of by this Certificate of Incorporation), shall be required to amend or repeal such provisions of this Certificate of Incorporation.
* * * * * * * * * * *
A-1-4 2023 Proxy Statement graphic

TABLE OF CONTENTS

Appendix A-2: Marked Copy of Restated Certificate of Incorporation
* * * * * * * * * * *
UPWORK INC.

RESTATED CERTIFICATE OF INCORPORATION
ARTICLE I: NAME
The name of the corporation is Upwork Inc. (the “Corporation”).
ARTICLE II: AGENT FOR SERVICE OF PROCESS
The address of the Corporation’s registered office in the State of Delaware is 9 E. Loockerman Street, Suite 311, Dover, DE, 19901, Kent County. The name of the registered agent of the Corporation at that address is Registered Agent Solutions, Inc.
ARTICLE III: PURPOSE
The purpose of the Corporation is to engage in any lawful act or activity for which corporations may be organized under the General Corporation Law of the State of Delaware (the “General Corporation Law”).
ARTICLE IV: AUTHORIZED STOCK
1. Total Authorized. The total number of shares of all classes of stock that the Corporation has authority to issue is five hundred million (500,000,000) shares, consisting of two classes: four hundred and ninety million (490,000,000) shares of Common Stock, $0.0001 par value per share (“Common Stock”), and ten million (10,000,000) shares of Preferred Stock, $0.0001 par value per share (“Preferred Stock”).
2. Designation of Additional Series.
2.1. The Board of Directors recommends you vote FORof the following proposals 2. RatifyCorporation (the “Board”) is authorized, subject to any limitations prescribed by the appointmentlaw of PricewaterhouseCoopers LLP as our independent registered public accounting firmthe State of Delaware, to provide for the year ending December 31, 2021. 3. Approve, on a non-binding advisory basis, the compensation of our named executive officers. NOTE: Such other business as may properly come before the meeting or any adjournment or postponement thereof. For All Withhold All For All Except To withhold authority to vote for any individual nominee(s), mark "For All Except" and write the number(s) of the nominee(s) on the line below. For Against Abstain Please sign exactly as your name(s) appear(s) hereon. When signing as attorney, executor, administrator, or other fiduciary, please give full title as such. Joint owners should each sign personally. All holders must sign. If a corporation or partnership, please sign in full corporate or partnership name by authorized officer. Signature [PLEASE SIGN WITHIN BOX] Date Signature (Joint Owners) Date

Important Notice Regarding the Availability of Proxy Materials for the Annual Meeting: The Notice and Proxy Statement and Annual Report on Form 10-K are available at www.proxyvote.com. D37217-P49965 UPWORK INC. Annual Meeting of Stockholders June 1, 2021 8:00 A.M. Pacific Time This proxy is solicited by the Board of Directors The undersigned hereby appoints Hayden Brown and Brian Levey, or either of them, as proxies, each with the power to appoint her or his substitute, and hereby authorizes them to represent and to vote, as designated on the reverse side of this ballot, allissuance of the shares of commonPreferred Stock in one or more series, and, by filing a Certificate of Designation pursuant to the applicable law of the State of Delaware (“Certificate of Designation”), to establish from time to time the number of shares to be included in each such series, to fix the designation, powers (including voting powers), preferences and relative, participating, optional or other special rights, if any, of the shares of each such series and any qualifications, limitations or restrictions thereof, and, except where otherwise provided in the applicable Certificate of Designation, to thereafter increase (but not above the total number of authorized shares of the Preferred Stock) or decrease (but not below the number of shares of such series then outstanding) the number of shares of any such series. The number of authorized shares of Preferred Stock may also be increased or decreased (but not below the number of shares thereof then outstanding) by the affirmative vote of the holders of two-thirds of the voting power of all of the then-outstanding shares of capital stock of UPWORK INC. that the undersigned isCorporation entitled to vote thereon, without a separate vote of the holders of the Preferred Stock, irrespective of the provisions of Section 242(b)(2) of the General Corporation Law, unless a separate vote of the holders of one or more series is required pursuant to the terms of any Certificate of Designation; provided, however, that if two-thirds of the Whole Board (as defined below) has approved such increase or decrease of the number of authorized shares of Preferred Stock, then only the affirmative vote of the holders of a majority of the voting power of all of the then-outstanding shares of the capital stock of the Corporation entitled to vote generally in the election of directors, voting together as a single class, without a separate vote of the holders of the Preferred Stock (unless a separate vote of the holders of one or more series is required pursuant to the terms of any Certificate of Designation), shall be required to effect such increase or decrease. For purposes of this Restated Certificate of Incorporation (as the same may be amended and/or restated from time to time, including pursuant the terms of any Certificate of Designation designating a series of Preferred Stock, this “Certificate of Incorporation”), the term “Whole Board” shall mean the total number of authorized directors whether or not there exist any vacancies in previously authorized directorships.

graphic2023 Proxy Statement A-2-1

TABLE OF CONTENTS

2.2 Except as otherwise expressly provided in any Certificate of Designation designating any series of Preferred Stock pursuant to the foregoing provisions of this Article IV, any new series of Preferred Stock may be designated, fixed and determined as provided herein by the Board without approval of the holders of Common Stock or the holders of Preferred Stock, or any series thereof, and any such new series may have powers, preferences and rights, including, without limitation, voting powers, dividend rights, liquidation rights, redemption rights and conversion rights, senior to, junior to or pari passu with the rights of the Common Stock, any series of Preferred Stock or any future class or series of capital stock of the Corporation.
2.3 Each outstanding share of Common Stock shall entitle the holder thereof to one vote on each matter properly submitted to the stockholders of the Corporation for their vote; provided, however, that, except as otherwise required by law, holders of Common Stock shall not be entitled to vote on any amendment to this Certificate of Incorporation that relates solely to the terms of one or more outstanding series of Preferred Stock if the holders of such affected series are entitled, either separately or together as a class with the holders of one or more other such series, to vote thereon pursuant to this Certificate of Incorporation.
ARTICLE V: AMENDMENT OF BYLAWS
The Board shall have the power to adopt, amend or repeal the Bylaws of the Corporation (as the same may be amended and/or restated from time to time, the “Bylaws”). Any adoption, amendment or repeal of the Bylaws by the Board shall require the approval of a majority of the Whole Board. The stockholders shall also have power to adopt, amend or repeal the Bylaws; provided, however, that notwithstanding any other provision of this Certificate of Incorporation or any provision of law that might otherwise permit a lesser or no vote, but in addition to any vote of the holders of any class or series of stock of the Corporation required by applicable law or by this Certificate of Incorporation, the affirmative vote of the holders of at least two-thirds of the voting power of all of the then-outstanding shares of the capital stock of the Corporation entitled to vote generally in the election of directors, voting together as a single class, shall be required for the stockholders to adopt, amend or repeal any provision of the Bylaws; provided further, that, in the case of any proposed adoption, amendment or repeal of any provisions of the Bylaws that is approved by the Board and submitted to the stockholders for adoption thereby, if two-thirds of the Whole Board has approved such adoption, amendment or repeal of any provisions of the Bylaws, then only the affirmative vote of the holders of a majority of the voting power of all of the then-outstanding shares of the capital stock of the Corporation entitled to vote generally in the election of directors, voting together as a single class, shall be required to adopt, amend or repeal any provision of the Bylaws.
ARTICLE VI: MATTERS RELATING TO THE BOARD OF DIRECTORS
1. Director Powers. Except as otherwise provided by the General Corporation Law or this Certificate of Incorporation, the business and affairs of the Corporation shall be managed by or under the direction of the Board.
2. Number of Directors. Subject to the special rights of the holders of any series of Preferred Stock to elect additional directors under specified circumstances, the total number of directors constituting the Whole Board shall be fixed from time to time exclusively by resolution adopted by a majority of the Whole Board.
3. Classified Board. Subject to the special rights of the holders of one or more series of Preferred Stock to elect additional directors under specified circumstances, the directors shall be divided, with respect to the time for which they severally hold office, into three classes designated as Class I, Class II and Class III, respectively (the “Classified Board”). The Board may assign members of the Board already in office to the Classified Board. The number of directors in each class shall be as nearly equal as is practicable. The initial term of office of the Class I directors shall expire at the Annual MeetingCorporation’s first annual meeting of Stockholdersstockholders following the closing of the Corporation’s initial public offering pursuant to an effective registration statement under the Securities Act of 1933, as amended, relating to the offer and sale of Common Stock to the public (the “Initial Public Offering”), the initial term of office of the Class II directors shall expire at the Corporation’s second annual meeting of stockholders following the closing of the Initial Public Offering and the initial term of office of the Class III directors shall expire at the Corporation’s third annual meeting of stockholders following the closing of the Initial Public Offering. At each annual meeting of stockholders following the closing of the Initial Public Offering, directors elected to succeed those directors of the class whose terms then expire shall be held on Tuesday, June 1, 2021elected for a term of office expiring at 8:00 A.M. Pacific Timethe third succeeding annual meeting of stockholders after their election.
A-2-2 2023 Proxy Statement graphic

TABLE OF CONTENTS

4. Term and Removal. Each director shall hold office until the annual meeting at which such director’s term expires and until such director’s successor is duly elected and qualified, or until such director’s earlier death, resignation, disqualification or removal. Any director may resign by visiting www.virtualshareholdermeeting.com/UPWK2021,delivering a resignation in writing or by electronic transmission to the Corporation at its principal office or to the Chairperson of the Board, the Chief Executive Officer, or the Secretary. Subject to the special rights of the holders of any series of Preferred Stock, no director may be removed from the Board except for cause and only by the affirmative vote of the holders of at least two-thirds of the voting power of the then-outstanding shares of capital stock of the Corporation entitled to vote thereon, voting together as a single class. In the event of any increase or decrease in the authorized number of directors, (a) each director then serving as such shall nevertheless continue as a director of the class of which he or she is a member and (b) the newly created or eliminated directorships resulting from such increase or decrease shall be apportioned by the Board among the classes of directors so as to make all classes as nearly equal in number as is practicable, provided that no decrease in the number of directors constituting the Board shall shorten the term of any director.
5. Board Vacancies and Newly Created Directorships. Subject to the special rights of the holders of any series of Preferred Stock, any vacancy occurring in the Board for any cause, and any adjournment or postponement thereof. This proxy, when properly executed, will be votednewly created directorship resulting from any increase in the manner directed herein. If no such direction is made, this proxy willauthorized number of directors, shall be votedfilled only by the affirmative vote of a majority of the directors then in office, even if less than a quorum, or by a sole remaining director, and shall not be filled by the stockholders. Any director elected in accordance with the preceding sentence shall hold office for a term expiring at the annual meeting of stockholders at which the term of office of the class to which the director has been assigned expires and until such director’s successor shall have been duly elected and qualified, or until such director’s earlier death, resignation, disqualification or removal.
6. Vote by Ballot. Election of directors need not be by written ballot unless the Bylaws shall so provide.
7. Preferred Directors. If and for so long as the holders of any series of Preferred Stock have the special right to elect additional directors, then upon commencement and for the duration of the period during which such right continues: (i) the then otherwise total authorized number of directors of the Corporation shall automatically be increased by such specified number of directors, and the holders of such Preferred Stock shall be entitled to elect the additional directors so provided for or fixed pursuant to said provisions, and (ii) each such additional director shall serve until such director’s successor shall have been duly elected and qualified, or until such director’s right to hold such office terminates pursuant to said provisions, whichever occurs earlier, subject to his or her earlier death, resignation, retirement, disqualification or removal. Except as otherwise provided by the Board in the resolution or resolutions establishing such series, whenever the holders of Directors' recommendations. Continuedany series of Preferred Stock having such right to elect additional directors are divested of such right pursuant to the provisions of such stock, the terms of office of all such additional directors elected by the holders of such stock, or elected to fill any vacancies resulting from the death, resignation, disqualification or removal of such additional directors, shall forthwith terminate and the total authorized number of directors of the Corporation shall be reduced accordingly.
ARTICLE VII: DIRECTOR AND OFFICER LIABILITY
1. Limitation of Liability. To the fullest extent permitted by law, noneither adirector nor an officer of the Corporation shall be personally liable to the Corporation or its stockholders for monetary damages for breach of fiduciary duty as a director or officer, as applicable. Without limiting the effect of the preceding sentence, if the General Corporation Law is hereafter amended to authorize the further elimination or limitation of the liability of a director or officer, then the liability of a director or officer of the Corporation shall be eliminated or limited to the fullest extent permitted by the General Corporation Law, as so amended.
2. Change in Rights. Neither any amendment nor repeal of this Article VII, nor the adoption of any provision of this Certificate of Incorporation inconsistent with this Article VII, shall eliminate, reduce or otherwise adversely affect any limitation on the personal liability of a director or officer of the Corporation existing at the time of such amendment, repeal or adoption of such an inconsistent provisionhereunder with respect to any act or omission occurring prior to such amendment, modification or repeal.
ARTICLE VIII: MATTERS RELATING TO STOCKHOLDERS
1. No Action by Written Consent of Stockholders. Subject to the rights of any series of Preferred Stock then outstanding, no action shall be taken by the stockholders of the Corporation except at a duly called annual or special meeting of stockholders and no action shall be taken by the stockholders of the Corporation by written consent in lieu of a meeting.
graphic2023 Proxy Statement A-2-3

TABLE OF CONTENTS

2. Special Meeting of Stockholders. Special meetings of the stockholders of the Corporation may be called only by the Chairperson of the Board, the Chief Executive Officer, the Lead Independent Director (as defined in the Bylaws), the President, or the Board acting pursuant to a resolution adopted by a majority of the Whole Board and may not be called by the stockholders or any other person or persons.
3. Advance Notice of Stockholder Nominations and Business Transacted at Special Meetings. Advance notice of stockholder nominations for the election of directors of the Corporation and of business to be brought by stockholders before any meeting of stockholders of the Corporation shall be given in the manner provided in the Bylaws. Business transacted at special meetings of stockholders shall be limited to the purpose or purposes stated in the notice of meeting.
ARTICLE IX: CHOICE OF FORUM
Unless the Corporation consents in writing to the selection of an alternative forum, the Court of Chancery of the State of Delaware (or if the Court of Chancery does not have jurisdiction, the federal district court for the District of Delaware), to the fullest extent permitted by law, shall be the sole and exclusive forum for: (a) any derivative action or proceeding brought on behalf of the Corporation; (b) any action asserting a claim of breach of a fiduciary duty owed by, or other wrongdoing by, any director, officer, stockholder, employee or agent of the Corporation to the Corporation or the Corporation’s stockholders; (c) any action asserting a claim against the Corporation arising pursuant to any provision of the General Corporation Law, this Certificate of Incorporation or the Bylaws or as to which the General Corporation Law confers jurisdiction on the Court of Chancery of the State of Delaware; (d) any action to interpret, apply, enforce or determine the validity of this Certificate of Incorporation or the Bylaws; or(e) any action asserting a claim against the Corporation governed by the internal affairs doctrine; or (f) any action asserting an “internal corporate claim” as that term is defined in Section 115 of the General Corporation Law.
Any person or entity purchasing or otherwise acquiring or holding any interest in shares of capital stock of the Corporation shall be deemed to have notice of and to have consented to the provisions of this Article IX. Failure to enforce the foregoing provisions of this Article IX would cause the Corporation irreparable harm, and the Corporation shall be signed on reverse side

entitled to equitable relief, including injunctive relief and specific performance, to enforce the foregoing provisions.
ARTICLE X: AMENDMENT OF CERTIFICATE OF INCORPORATION
If any provision of this Certificate of Incorporation shall be held to be invalid, illegal, or unenforceable, then such provision shall nonetheless be enforced to the maximum extent possible consistent with such holding and the remaining provisions of this Certificate of Incorporation (including without limitation, all portions of any section of this Certificate of Incorporation containing any such provision held to be invalid, illegal, or unenforceable, which is not invalid, illegal, or unenforceable) shall remain in full force and effect.
The Corporation reserves the right to amend or repeal any provision contained in this Certificate of Incorporation in the manner prescribed by the laws of the State of Delaware and all rights conferred upon stockholders are granted subject to this reservation; provided, however, that, notwithstanding any provision of this Certificate of Incorporation or any provision of law that might otherwise permit a lesser vote or no vote (but subject to Section 2 of Article IV hereof), but in addition to any vote of the holders of any class or series of the stock of the Corporation required by law or by this Certificate of Incorporation, the affirmative vote of the holders of at least two-thirds of the voting power of all of the then-outstanding shares of the capital stock of the Corporation entitled to vote generally in the election of directors, voting together as a single class, shall be required to amend or repeal any provision of this Certificate of Incorporation; provided, further, that if two-thirds of the Whole Board has approved such amendment or repeal of any provisions of this Certificate of Incorporation, then only the affirmative vote of the holders of at least a majority of the voting power of all of the then-outstanding shares of capital stock of the Corporation entitled to vote generally in the election of directors, voting together as a single class (in addition to any other vote of the holders of any class or series of stock of the Corporation required by law of by this Certificate of Incorporation), shall be required to amend or repeal such provisions of this Certificate of Incorporation.
* * * * * * * * * * *
A-2-4 2023 Proxy Statement graphic

TABLE OF CONTENTS

Appendix B: Reconciliation of Non-GAAP Financial Measures
This Proxy Statement includes references to Compensation Program Revenue, which is a non-GAAP measure of financial performance.
This non-GAAP measure is not prepared in accordance with, and is not an alternative to financial measures prepared in accordance with, GAAP. There are material limitations associated with the use of non-GAAP financial measures as an analytical tool, and non-GAAP financial measures should not be considered in isolation or as substitutes for analysis of financial results as reported under GAAP. The non-GAAP financial measure may be different from non-GAAP financial measures used by other companies, limiting its usefulness for comparison purposes. We compensate for these limitations by providing specific information regarding the GAAP items excluded from the non-GAAP financial measure. A reconciliation of the non-GAAP measure to its most directly comparable GAAP financial measure has been provided in the financial statement table below, and stockholders are encouraged to review the reconciliation.
Reconciliation of Revenue to Compensation Program Revenue
(in thousands)
2022
2021
2020
Marketplace revenue
$566,623
$462,340
$338,152
Managed services revenue
51,695
40,457
35,476
Total revenue
$618,318
$502,797
$373,628
Less:
Cost of talent services to deliver managed services
(37,749)
(31,871)
(28,703)
Compensation Program Revenue
$580,569
$470,926
$344,924
graphic2023 Proxy Statement B-1

TABLE OF CONTENTS

graphic

TABLE OF CONTENTS

graphic