UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, DC 20549

FORM 10-Q

(Mark One)


☒			QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For the quarterly period ended ~~September 30, 2022~~March 31, 2023


☐			TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934

For the transition period from _______ to _______

Commission File Number: 001-38678

UPWORK INC.

(Exact Name of Registrant as Specified in its Charter)


Delaware		46-4337682
(State or other jurisdiction of incorporation or organization)		(I.R.S. Employer Identification No.)
475 Brannan Street, Suite 430
San Francisco,	California	94107
(Address of principal executive offices)		(Zip Code)

(650) 316-7500

(Registrant’s telephone number, including area code)

Securities registered pursuant to Section 12(b) of the Act:


Title of Each Class	Trading Symbol	Name of Each Exchange on Which Registered
Common Stock, $0.0001 par value per share	UPWK	The Nasdaq Stock Market LLC

Indicate by check mark whether the registrant (1) has filed all reports required to be filed by Section 13 or 15(d) of the Securities Exchange Act of 1934 during the preceding 12 months (or for such shorter period that the registrant was required to file such reports), and (2) has been subject to such filing requirements for the past 90 days. Yes ☒ No ☐

Indicate by check mark whether the registrant has submitted electronically every Interactive Data File required to be submitted pursuant to Rule 405 of Regulation S-T (§232.405 of this chapter) during the preceding 12 months (or for such shorter period that the registrant was required to submit such files). Yes ☒ No ☐

Indicate by check mark whether the registrant is a large accelerated filer, an accelerated filer, a non-accelerated filer, a smaller reporting company, or an emerging growth company. See the definitions of “large accelerated filer,” “accelerated filer,” “smaller reporting company,” and “emerging growth company” in Rule 12b-2 of the Exchange Act.

Large accelerated filer

☒

Accelerated filer

☐

Non-accelerated filer

☐

Smaller reporting company

☐

Emerging growth company

☐

If an emerging growth company, indicate by check mark if the registrant has elected not to use the extended transition period for complying with any new or revised financial accounting standards provided pursuant to Section 13(a) of the Exchange Act. ☐

Indicate by check mark whether the registrant is a shell company (as defined in Rule 12b-2 of the Exchange Act). Yes ☐ No ☒

As of ~~September 30, 2022,~~March 31, 2023, there were ~~131,342,482~~133,464,264 shares of the registrant’s common stock outstanding.

TABLE OF CONTENTS


		Page
Special Note Regarding Forward-Looking Statements		1

PART I—FINANCIAL INFORMATION
Item 1.	Financial Statements (Unaudited)
	Condensed Consolidated Balance Sheets as of ~~September 30, 2022~~March 31, 2023 and December 31, ~~2021~~2022	2
	Condensed Consolidated Statements of Operations and Comprehensive ~~Loss~~Income (Loss) for the Three ~~and Nine~~ Months Ended ~~September 30,~~March 31, 2023 and 2022 ~~and 2021~~	3
	Condensed Consolidated Statements of Stockholders’ Equity for the Three ~~and Nine~~ Months Ended ~~September 30,~~March 31, 2023 and 2022 ~~and 2021~~	4
	Condensed Consolidated Statements of Cash Flows for the ~~Nine~~Three Months Ended ~~September 30,~~March 31, 2023 and 2022 ~~and 2021~~	5
	Notes to Condensed Consolidated Financial Statements	6
Item 2.	Management’s Discussion and Analysis of Financial Condition and Results of Operations	1718
Item 3.	Quantitative and Qualitative Disclosures About Market Risk	30
Item 4.	Controls and Procedures	31

PART II—OTHER INFORMATION
Item 1.	Legal Proceedings	32
Item 1A.	Risk Factors	32
Item 2.	Unregistered Sales of Equity Securities and Use of Proceeds	8372
Item 3.	Defaults Upon Senior Securities	72
Item 4.	Mine Safety Disclosures	72
Item 5.	Other Information	73
Item 6.	Exhibits	8474
Signatures		8575

Unless otherwise expressly stated or the context otherwise requires, references in this Quarterly Report on Form 10-Q, which we refer to as this Quarterly Report, to “Upwork,” “Company,” “our,” “us,” and “we” and similar references refer to Upwork Inc. and its ~~wholly-owned~~wholly owned subsidiaries.

SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS

This Quarterly Report contains forward-looking statements within the meaning of the federal securities laws. All statements contained in this Quarterly Report, other than statements of historical fact, including statements regarding our future operating results and financial position, our business strategy and plans, potential growth or growth prospects, active clients, future research and development, sales and marketing and general and administrative expenses, provision for transaction losses, our objectives for future operations, and potential impacts ofas the ~~ongoing~~ COVID-19 pandemic potential impacts of Russia’s invasion of Ukraine and our decision to suspend our business operations in Russia and Belarus, or expectations regarding actions we may take in response to the pandemic or to the war in Ukraine,subsides, are forward-looking statements. Words such as “believes,” “may,” “will,” “estimates,” “potential,” “continues,” “anticipates,” “intends,” “expects,” “could,” “would,” “projects,” “plans,” “targets,” and variations of such words and similar expressions are intended to identify forward-looking statements.

We have based these forward-looking statements largely on our current expectations and projections as of the date of this filing about future events and trends that we believe may affect our financial condition, results of operations, business strategy, short-term and long-term business operations and objectives, and financial needs. These forward-looking statements are subject to a number of risks, uncertainties and assumptions, including those described in Part II, Item 1A, “Risk Factors” in this Quarterly ~~Report and the impact of the ongoing COVID-19 pandemic and ongoing Russian war against Ukraine.~~Report. Readers are urged to carefully review and consider the various disclosures made in this Quarterly Report and in other documents we file from time to time with the Securities and Exchange Commission, which we refer to as the SEC, that disclose risks and uncertainties that may affect our business. Moreover, we operate in a very competitive and rapidly changing environment. New risks emerge from time to time. It is not possible for us to predict all risks, nor can we assess the impact of all factors on our business or the extent to which any factor, or combination of factors, may cause actual results to differ materially from those contained in any forward-looking statements we may make. In light of these risks, uncertainties, and assumptions, the future events and circumstances discussed in this Quarterly Report may not occur and actual results could differ materially and adversely from those anticipated or implied in the forward-looking statements.

You should not rely upon forward-looking statements as predictions of future events. The events and circumstances reflected in the forward-looking statements may not be achieved or occur. Although we believe that the expectations reflected in the forward-looking statements are reasonable, we cannot guarantee future results, performance, or achievements. In addition, the forward-looking statements in this Quarterly Report are made as of the date of this filing, and we do not undertake, and expressly disclaim any duty, to update such statements for any reason after the date of this Quarterly Report or to conform statements to actual results or revised expectations, except as required by law.

You should read this Quarterly Report and the documents that we reference herein and have filed with the SEC as exhibits to this Quarterly Report with the understanding that our actual future results, performance, and events and circumstances may be materially different from what we expect.


PART I—FINANCIAL INFORMATION

Item 1. Financial Statements.

UPWORK INC.

CONDENSED CONSOLIDATED BALANCE SHEETS

(Unaudited)


(In thousands, except share and per share data)	(In thousands, except share and per share data)	September 30, 2022		December 31, 2021		(In thousands, except share and per share data)	March 31, 2023		December 31, 2022
ASSETS	ASSETS					ASSETS
Current assets	Current assets					Current assets
Cash and cash equivalents	Cash and cash equivalents	$	156,423	$	187,205	Cash and cash equivalents	$	101,985	$	129,384
Marketable securities	Marketable securities	519,383		497,566		Marketable securities	407,643		557,230
Funds held in escrow, including funds in transit	Funds held in escrow, including funds in transit	169,966		160,813		Funds held in escrow, including funds in transit	179,420		161,457
Trade and client receivables – net of allowance of $16,099 and $3,410 as of September 30, 2022 and December 31, 2021, respectively		67,070		66,826
Trade and client receivables – net of allowance of $9,018 and $12,464 as of March 31, 2023 and December 31, 2022, respectively						Trade and client receivables – net of allowance of $9,018 and $12,464 as of March 31, 2023 and December 31, 2022, respectively	59,291		64,888
Prepaid expenses and other current assets	Prepaid expenses and other current assets	16,860		17,243		Prepaid expenses and other current assets	19,481		17,947
Total current assets	Total current assets	929,702		929,653		Total current assets	767,820		930,906
Property and equipment, net	Property and equipment, net	21,487		21,329		Property and equipment, net	23,104		22,063
Goodwill	Goodwill	118,219		118,219		Goodwill	118,219		118,219

Operating lease asset	Operating lease asset	8,387		10,682		Operating lease asset	6,803		7,603
Other assets, noncurrent	Other assets, noncurrent	1,431		1,178		Other assets, noncurrent	2,120		1,454
Total assets	Total assets	$	1,079,226	$	1,081,061	Total assets	$	918,066	$	1,080,245

LIABILITIES AND STOCKHOLDERS’ EQUITY	LIABILITIES AND STOCKHOLDERS’ EQUITY					LIABILITIES AND STOCKHOLDERS’ EQUITY
Current liabilities	Current liabilities					Current liabilities
Accounts payable	Accounts payable	$	5,354	$	4,996	Accounts payable	$	4,248	$	7,549
Escrow funds payable	Escrow funds payable	169,966		160,813		Escrow funds payable	179,420		161,457

Accrued expenses and other current liabilities	Accrued expenses and other current liabilities	51,781		45,742		Accrued expenses and other current liabilities	47,595		53,611
Deferred revenue	Deferred revenue	24,910		22,083		Deferred revenue	25,557		25,075
Total current liabilities	Total current liabilities	252,011		233,634		Total current liabilities	256,820		247,692
Debt, noncurrent	Debt, noncurrent	563,520		561,299		Debt, noncurrent	354,705		564,261
Operating lease liability, noncurrent	Operating lease liability, noncurrent	12,619		16,753		Operating lease liability, noncurrent	9,713		11,177
Other liabilities, noncurrent	Other liabilities, noncurrent	8,493		9,858		Other liabilities, noncurrent	7,872		8,236
Total liabilities	Total liabilities	836,643		821,544		Total liabilities	629,110		831,366

Commitments and contingencies (Note 6)	Commitments and contingencies (Note 6)					Commitments and contingencies (Note 6)

Stockholders’ equity	Stockholders’ equity					Stockholders’ equity
Common stock, $0.0001 par value; 490,000,000 shares authorized as of September 30, 2022 and December 31, 2021; 131,342,482 and 129,130,478 shares issued and outstanding as of September 30, 2022 and December 31, 2021, respectively		13		13
Common stock, $0.0001 par value; 490,000,000 shares authorized as of March 31, 2023 and December 31, 2022; 133,464,264 and 132,368,265 shares issued and outstanding as of March 31, 2023 and December 31, 2022, respectively						Common stock, $0.0001 par value; 490,000,000 shares authorized as of March 31, 2023 and December 31, 2022; 133,464,264 and 132,368,265 shares issued and outstanding as of March 31, 2023 and December 31, 2022, respectively	13		13
Additional paid-in capital	Additional paid-in capital	571,636		511,096		Additional paid-in capital	613,887		592,900
Accumulated other comprehensive loss	Accumulated other comprehensive loss	(4,617)		(528)		Accumulated other comprehensive loss	(1,162)		(3,085)
Accumulated deficit	Accumulated deficit	(324,449)		(251,064)		Accumulated deficit	(323,782)		(340,949)
Total stockholders’ equity	Total stockholders’ equity	242,583		259,517		Total stockholders’ equity	288,956		248,879
Total liabilities and stockholders’ equity	Total liabilities and stockholders’ equity	$	1,079,226	$	1,081,061	Total liabilities and stockholders’ equity	$	918,066	$	1,080,245

The accompanying notes are an integral part of these condensed consolidated financial statements.

UPWORK INC.

CONDENSED CONSOLIDATED STATEMENTS OF OPERATIONS

AND COMPREHENSIVE ~~LOSS~~INCOME (LOSS)

(Unaudited)


		Three Months Ended September 30,				Nine Months Ended September 30,					Three Months Ended March 31,
(In thousands, except per share data)	(In thousands, except per share data)	2022		2021		2022		2021		(In thousands, except per share data)	2023		2022
Revenue	Revenue	$	158,641	$	128,141	$	456,876	$	365,941	Revenue	$	160,858	$	141,337
Cost of revenue	Cost of revenue	40,470		34,933		119,243		98,457		Cost of revenue	40,427		37,916
Gross profit	Gross profit	118,171		93,208		337,633		267,484		Gross profit	120,431		103,421
Operating expenses	Operating expenses									Operating expenses
Research and development	Research and development	38,898		30,873		112,889		85,610		Research and development	44,481		38,161
Sales and marketing	Sales and marketing	63,171		43,192		184,096		128,613		Sales and marketing	65,000		57,642
General and administrative	General and administrative	31,407		26,083		93,872		81,969		General and administrative	29,287		29,141
Provision for transaction losses	Provision for transaction losses	10,137		1,377		18,918		3,701		Provision for transaction losses	6,701		2,129
Total operating expenses	Total operating expenses	143,613		101,525		409,775		299,893		Total operating expenses	145,469		127,073
Loss from operations	Loss from operations	(25,442)		(8,317)		(72,142)		(32,409)		Loss from operations	(25,038)		(23,652)
Interest expense	Interest expense	1,117		746		3,362		1,055		Interest expense	1,101		1,125
Other (income) expense, net		(1,772)		222		(2,215)		161
Loss before income taxes		(24,787)		(9,285)		(73,289)		(33,625)
Other income, net										Other income, net	(44,101)		(68)
Income (loss) before income taxes										Income (loss) before income taxes	17,962		(24,709)
Income tax provision	Income tax provision	(40)		(26)		(96)		(59)		Income tax provision	(795)		(29)
Net loss		$	(24,827)	$	(9,311)	$	(73,385)	$	(33,684)
Net income (loss)										Net income (loss)	$	17,167	$	(24,738)

Net loss per share, basic and diluted		$	(0.19)	$	(0.07)	$	(0.56)	$	(0.27)
Weighted-average shares used to compute net loss per share, basic and diluted		130,830		127,915		130,083		126,651
Net income (loss) per share:										Net income (loss) per share:
Basic										Basic	$	0.13	$	(0.19)
Diluted										Diluted	$	(0.15)	$	(0.19)

Other comprehensive loss, net of tax:
Weighted-average shares used to compute net income (loss) per share										Weighted-average shares used to compute net income (loss) per share
Basic										Basic	132,836		129,359
Diluted										Diluted	135,966		129,359

Other comprehensive income (loss), net of tax:										Other comprehensive income (loss), net of tax:
Net unrealized holding gain (loss) on marketable securities, net	Net unrealized holding gain (loss) on marketable securities, net	$	166	$	(5)	$	(4,089)	$	(30)	Net unrealized holding gain (loss) on marketable securities, net	$	1,923	$	(2,850)
Total comprehensive loss		(24,661)		(9,316)		(77,474)		(33,714)
Total comprehensive income (loss)										Total comprehensive income (loss)	19,090		(27,588)

The accompanying notes are an integral part of these condensed consolidated financial statements.

UPWORK INC.

CONDENSED CONSOLIDATED STATEMENTS OF STOCKHOLDERS’ EQUITY

(Unaudited)


(In thousands, except share amounts)	(In thousands, except share amounts)	Common Stock		Additional Paid-in Capital			Accumulated Other Comprehensive Loss		Accumulated Deficit				Total Stockholders’ Equity		(In thousands, except share amounts)						Common Stock	Additional Paid-in Capital		Accumulated Other Comprehensive Loss		Accumulated Deficit			Total Stockholders’ Equity
Three Months Ended September 30, 2022			Shares			Amount
Balances as of June 30, 2022			130,530,889	$	13		$	550,711			$	(4,783)				$	(299,622)		$	246,319
Three Months Ended March 31, 2023																		Three Months Ended March 31, 2023					Shares					Additional Paid-in Capital	Amount		Accumulated Other Comprehensive Loss			Accumulated Deficit			Total Stockholders’ Equity
Balances as of December 31, 2022																		Balances as of December 31, 2022				132,368,265							$	248,879
Issuance of common stock upon exercise of stock options	Issuance of common stock upon exercise of stock options		81,115	—			291		—				—			291		Issuance of common stock upon exercise of stock options				223,251		—		758					—			—			758
Stock-based compensation expense	Stock-based compensation expense		—	—			20,446		—				—			20,446		Stock-based compensation expense				—		—		20,041			—			—			20,041
Issuance of common stock for settlement of RSUs	Issuance of common stock for settlement of RSUs		730,478	—			—		—				—			—		Issuance of common stock for settlement of RSUs				872,748		—		—			—			—			—
Tides Foundation common stock warrant expense	Tides Foundation common stock warrant expense		—	—			188		—				—			188		Tides Foundation common stock warrant expense				—		—		188			—			—			188

Issuance of common stock in connection with employee stock purchase plan																		Issuance of common stock in connection with employee stock purchase plan				—		—		—			—			—			—
Unrealized gain on marketable securities	Unrealized gain on marketable securities		—	—			—		166				—			166		Unrealized gain on marketable securities				—		—		—			1,923			—			1,923
Net loss			—	—			—		—				(24,827)			(24,827)
Balances as of September 30, 2022			131,342,482	$	13		$	571,636	$	(4,617)			$	(324,449)		$	242,583
Net income																		Net income				—		—		—			—			17,167			17,167
Balances as of March 31, 2023																		Balances as of March 31, 2023				133,464,264		$	13	$	613,887		$	(1,162)		$	(323,782)		$	288,956

(In thousands, except share amounts) Common Stock Additional Paid-in Capital Accumulated
Other Comprehensive Loss Accumulated
Deficit Total
Stockholders’
Equity
Three Months Ended September 30, 2021 Shares Amount
Balances as of June 30, 2021 127,616,789 $ 13 $ 527,718 $ (6) $ (219,197) $ 308,528
Issuance of common stock upon exercise of stock options 224,785 — 909 — — 909
Stock-based compensation expense — — 13,917 — — 13,917
Issuance of common stock for settlement of RSUs 391,971 — — — — —
Tides Foundation common stock warrant expense — — 188 — — 188
Purchases of capped calls related to convertible senior notes — — (49,393) — — (49,393)
Unrealized loss on marketable securities — — — (5) — (5)
Net loss — — — — (9,311) (9,311)
Balances as of September 30, 2021 128,233,545 $ 13 $ 493,339 $ (11) $ (228,508) $ 264,833

(In thousands, except share amounts) Common Stock Additional Paid-in Capital Accumulated
Other Comprehensive Loss Accumulated
Deficit Total
Stockholders’
Equity
Nine Months Ended September 30, 2022 Shares Amount
Balances as of December 31, 2021 129,130,478 $ 13 $ 511,096 $ (528) $ (251,064) $ 259,517
Issuance of common stock upon exercise of stock options 352,336 — 1,335 — — 1,335
Stock-based compensation expense — — 56,180 — — 56,180
Issuance of common stock for settlement of RSUs 1,698,043 — — — — —
Tides Foundation common stock warrant expense — — 563 — — 563
Issuance of common stock in connection with employee stock purchase plan 161,625 — 2,462 — — 2,462
Unrealized loss on marketable securities — — — (4,089) — (4,089)
Net loss — — — — (73,385) (73,385)
Balances as of September 30, 2022 131,342,482 $ 13 $ 571,636 $ (4,617) $ (324,449) $ 242,583


(In thousands, except share amounts)	(In thousands, except share amounts)	Common Stock		Additional Paid-in Capital			Accumulated Other Comprehensive Income (Loss)		Accumulated Deficit				Total Stockholders’ Deficit		(In thousands, except share amounts)						Common Stock	Additional Paid-in Capital	Accumulated Other Comprehensive Loss			Accumulated Deficit		Total Stockholders’ Equity
Nine Months Ended September 30, 2021			Shares			Amount
Balances as of December 31, 2020			124,795,222	$	12		$	494,103			$	19				$	(194,824)		$	299,310

Three Months Ended March 31, 2022																		Three Months Ended March 31, 2022				Shares	Additional Paid-in Capital		Amount	Accumulated Other Comprehensive Loss		Accumulated Deficit				Total Stockholders’ Equity
Balances as of December 31, 2021																		Balances as of December 31, 2021				129,130,478								$	259,517
Issuance of common stock upon exercise of stock options	Issuance of common stock upon exercise of stock options		1,899,902	1			6,635		—				—			6,636		Issuance of common stock upon exercise of stock options				124,094			—			488				—		—		488
Stock-based compensation expense	Stock-based compensation expense		—	—			38,743		—				—			38,743		Stock-based compensation expense				—	—			16,744		—				—		16,744
Issuance of common stock for settlement of RSUs	Issuance of common stock for settlement of RSUs		1,302,963	—			—		—				—			—		Issuance of common stock for settlement of RSUs				396,646	—			—		—				—		—
Tides Foundation common stock warrant expense	Tides Foundation common stock warrant expense		—	—			563		—				—			563		Tides Foundation common stock warrant expense				—	—			188		—				—		188
Issuance of common stock in connection with employee stock purchase plan			235,458	—			2,688		—				—			2,688
Purchases of capped calls related to convertible senior notes			—	—			(49,393)		—				—			(49,393)

Unrealized loss on marketable securities	Unrealized loss on marketable securities		—	—			—		(30)				—			(30)		Unrealized loss on marketable securities				—	—			—		(2,850)				—		(2,850)
Net loss	Net loss		—	—			—		—				(33,684)			(33,684)		Net loss				—	—			—		—				(24,738)		(24,738)
Balances as of September 30, 2021			128,233,545	$	13		$	493,339	$	(11)			$	(228,508)		$	264,833
Balances as of March 31, 2022																		Balances as of March 31, 2022				129,651,218	$	13		$	528,516	$	(3,378)			$	(275,802)	$	249,349

The accompanying notes are an integral part of these condensed consolidated financial statements.

UPWORK INC.

CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS

(Unaudited)


		Nine Months Ended September 30,					Three Months Ended March 31,
(In thousands)	(In thousands)	2022		2021		(In thousands)	2023		2022
CASH FLOWS FROM OPERATING ACTIVITIES:	CASH FLOWS FROM OPERATING ACTIVITIES:					CASH FLOWS FROM OPERATING ACTIVITIES:
Net loss		$	(73,385)	$	(33,684)
Adjustments to reconcile net loss to net cash provided by (used in) operating activities:
Net income (loss)						Net income (loss)	$	17,167	$	(24,738)
Adjustments to reconcile net income (loss) to net cash used in operating activities:						Adjustments to reconcile net income (loss) to net cash used in operating activities:
Provision for transaction losses	Provision for transaction losses	18,412		3,004		Provision for transaction losses	3,712		1,919
Depreciation and amortization		6,007		8,187
Depreciation						Depreciation	2,024		2,009
Amortization of debt issuance costs	Amortization of debt issuance costs	2,221		441		Amortization of debt issuance costs	716		740
Amortization of premium of purchases of marketable securities, net		485		103
Amortization of premium (accretion of discount) of purchases of marketable securities, net						Amortization of premium (accretion of discount) of purchases of marketable securities, net	(3,487)		537
Amortization of operating lease asset	Amortization of operating lease asset	2,295		2,712		Amortization of operating lease asset	800		751
Tides Foundation common stock warrant expense	Tides Foundation common stock warrant expense	563		563		Tides Foundation common stock warrant expense	188		188
Stock-based compensation expense	Stock-based compensation expense	56,119		38,666		Stock-based compensation expense	19,900		16,735

Impairment expense		—		7,389
Gain on early extinguishment of debt						Gain on early extinguishment of debt	(38,945)		—
Changes in operating assets and liabilities:	Changes in operating assets and liabilities:					Changes in operating assets and liabilities:
Trade and client receivables	Trade and client receivables	(17,764)		(13,967)		Trade and client receivables	1,990		2,990
Prepaid expenses and other assets	Prepaid expenses and other assets	380		(2,163)		Prepaid expenses and other assets	(1,360)		(1,394)
Operating lease liability	Operating lease liability	(3,994)		114		Operating lease liability	(1,419)		(1,292)
Accounts payable	Accounts payable	278		(3,188)		Accounts payable	(3,380)		1,150
Accrued expenses and other liabilities	Accrued expenses and other liabilities	2,202		9,987		Accrued expenses and other liabilities	(6,855)		(12,734)
Deferred revenue	Deferred revenue	4,285		5,120		Deferred revenue	248		1,663
Net cash provided by (used in) operating activities		(1,896)		23,284
Net cash used in operating activities						Net cash used in operating activities	(8,701)		(11,476)
CASH FLOWS FROM INVESTING ACTIVITIES:	CASH FLOWS FROM INVESTING ACTIVITIES:					CASH FLOWS FROM INVESTING ACTIVITIES:
Purchases of marketable securities	Purchases of marketable securities	(398,259)		(108,828)		Purchases of marketable securities	(156,128)		(160,251)
Proceeds from maturities of marketable securities	Proceeds from maturities of marketable securities	371,879		87,500		Proceeds from maturities of marketable securities	167,416		106,634
Proceeds from sale of marketable securities						Proceeds from sale of marketable securities	143,709		—
Purchases of property and equipment	Purchases of property and equipment	(893)		(565)		Purchases of property and equipment	(158)		(193)
Internal-use software and platform development costs	Internal-use software and platform development costs	(5,160)		(4,221)		Internal-use software and platform development costs	(2,703)		(1,233)
Net cash used in investing activities		(32,433)		(26,114)
Net cash provided by (used in) investing activities						Net cash provided by (used in) investing activities	152,136		(55,043)
CASH FLOWS FROM FINANCING ACTIVITIES:	CASH FLOWS FROM FINANCING ACTIVITIES:					CASH FLOWS FROM FINANCING ACTIVITIES:

Changes in escrow funds payable	Changes in escrow funds payable	9,153		37,649		Changes in escrow funds payable	17,963		35,566
Proceeds from exercises of stock options	Proceeds from exercises of stock options	1,335		6,636		Proceeds from exercises of stock options	758		488

Proceeds from employee stock purchase plan		2,462		2,688

Repayment of debt		—		(10,750)
Proceeds from issuance of convertible senior notes		—		575,000
Payment of debt issuance costs		—		(14,855)
Purchases of capped calls related to convertible senior notes		—		(49,393)
Net cash paid for early extinguishment of debt						Net cash paid for early extinguishment of debt	(170,752)		—

Net cash provided by financing activities		12,950		546,975
Net cash provided by (used in) financing activities						Net cash provided by (used in) financing activities	(152,031)		36,054
NET CHANGE IN CASH, CASH EQUIVALENTS, AND RESTRICTED CASH	NET CHANGE IN CASH, CASH EQUIVALENTS, AND RESTRICTED CASH	(21,379)		544,145		NET CHANGE IN CASH, CASH EQUIVALENTS, AND RESTRICTED CASH	(8,596)		(30,465)
Cash, cash equivalents, and restricted cash—beginning of period	Cash, cash equivalents, and restricted cash—beginning of period	352,058		232,463		Cash, cash equivalents, and restricted cash—beginning of period	295,231		352,058
Cash, cash equivalents, and restricted cash—end of period	Cash, cash equivalents, and restricted cash—end of period	$	330,679	$	776,608	Cash, cash equivalents, and restricted cash—end of period	$	286,635	$	321,593
SUPPLEMENTAL DISCLOSURE OF CASH FLOW INFORMATION:	SUPPLEMENTAL DISCLOSURE OF CASH FLOW INFORMATION:					SUPPLEMENTAL DISCLOSURE OF CASH FLOW INFORMATION:

Cash paid for interest	Cash paid for interest	$	1,520	$	347	Cash paid for interest	$	811	$	763
SUPPLEMENTAL DISCLOSURES OF NON-CASH INVESTING ACTIVITIES:	SUPPLEMENTAL DISCLOSURES OF NON-CASH INVESTING ACTIVITIES:					SUPPLEMENTAL DISCLOSURES OF NON-CASH INVESTING ACTIVITIES:
Property and equipment purchased but not yet paid	Property and equipment purchased but not yet paid	$	107	$	251	Property and equipment purchased but not yet paid	$	79	$	302
Internal-use software and platform development costs incurred but not yet paid	Internal-use software and platform development costs incurred but not yet paid	$	75	$	118	Internal-use software and platform development costs incurred but not yet paid	$	57	$	—

Marketable securities purchased but not yet paid						Marketable securities purchased but not yet paid	$	—	$	3,985

The accompanying notes are an integral part of these condensed consolidated financial statements.

UPWORK INC.

Notes to Condensed Consolidated Financial Statements

(Unaudited)

Note 1—Description of Business

Upwork Inc., which is referred to as the Company or Upwork, operates a work marketplace that connects businesses, which are referred to as clients, with independent talent. Independent talent on the Company’s work marketplace, which are referred to as talent, and, together with clients, as users, include independent professionals and agencies of varying sizes and are an increasingly sought-after, critical, and expanding segment of the global workforce. The Company is ~~currently~~ headquartered in San Francisco, California.

Unless otherwise expressly stated or the context otherwise requires, the terms “Upwork” and the “Company” in these notes to the condensed consolidated financial statements refer to Upwork and its ~~wholly-owned~~wholly owned subsidiaries.

Note 2—Basis of Presentation and Summary of Significant Accounting Policies

Basis of Presentation

The accompanying unaudited condensed consolidated financial statements have been prepared in accordance with generally accepted accounting principles in the United States, which is referred to as U.S. GAAP, and applicable rules and regulations of the SEC regarding interim financial reporting. Certain information and note disclosures normally included in the financial statements prepared in accordance with U.S. GAAP have been condensed or omitted pursuant to such rules and regulations. As such, the information included in this Quarterly Report should be read in conjunction with the consolidated financial statements and notes thereto included in the Company’s Annual Report on Form 10-K for the year ended December 31, ~~2021,~~2022, which is referred to as the Annual Report, filed with the SEC on February ~~15, 2022.~~16, 2023.

The condensed consolidated balance sheet as of December 31, ~~2021~~2022 included herein was derived from the audited financial statements as of that date but does not include all disclosures including notes required by U.S. GAAP.

The condensed consolidated financial statements include the accounts of Upwork and its ~~wholly-owned~~wholly owned subsidiaries. All intercompany balances and transactions have been eliminated.

The accompanying condensed consolidated financial statements reflect all normal recurring adjustments necessary to present fairly the financial position, results of operations, changes in stockholders’ equity and cash flows for the interim periods, but do not purport to be indicative of the results of operations or financial condition to be anticipated for the full year ending December 31, ~~2022. Prior period amounts~~ ~~have been reclassified to conform with the current period presentation.~~2023.

Use of Estimates

The preparation of the condensed consolidated financial statements in conformity with U.S. GAAP requires management to make certain estimates, judgments, and assumptions that affect the reported amounts of assets and liabilities, disclosure of contingent assets and liabilities at the date of the financial statements, and the reported amounts of revenue and expenses during the periods presented. Such estimates include, but are not limited to: the useful lives of assets; assessment of the recoverability of long-lived assets; goodwill impairment; standalone selling price of material rights and the period of time over which to defer and recognize the consideration allocated to the material rights; allowance for ~~doubtful accounts;~~expected credit losses; liabilities relating to transaction losses; stock-based compensation; and accounting for income taxes. Management bases its estimates on historical experience and on various other assumptions that management believes to be reasonable under the circumstances. The Company evaluates its estimates, assumptions, and judgments on an ongoing basis using historical experience and other factors and revises them when facts and circumstances dictate.

The Company is not aware of any specific event or circumstance that would require an update to its estimates or judgments or a revision of the carrying value of its assets or liabilities. These estimates may

change as new events occur and additional information is obtained. Actual results could differ materially from these estimates under different assumptions or conditions.

~~Risks and Uncertainties~~

Due to Russia’s invasion of Ukraine, which began in February 2022, and the resulting sanctions and other actions against Russia and Belarus, there has been uncertainty and disruption in the global economy. In March 2022, the Company suspended business operations in Russia and Belarus, announcing that contracts with talent or clients in Russia or Belarus would be required to wind down by May 1, 2022.

Although the Russian war against Ukraine did not have a material adverse impact on the Company’s revenue or other financial results for the three and nine months ended September 30, 2022, at this time the Company is unable to fully assess the aggregate impact the Russian war against Ukraine will have on its business due to various uncertainties, which include, but are not limited to, the duration of the war, the ability of talent based in Ukraine to continue working, the war’s effect on the economy, its impact to the businesses of the Company’s clients, and actions that may be taken by governmental authorities related to the war.

Summary of Significant Accounting Policies

The significant accounting policies applied in the Company’s audited consolidated financial statements, as disclosed in the Annual Report, are applied consistently in these unaudited interim condensed consolidated financial statements.

Recent Accounting Pronouncements Not Yet Adopted

The Company has reviewed the accounting pronouncements issued during the ~~nine~~three months ended ~~September 30, 2022~~March 31, 2023 and concluded they were either not applicable or not expected to have a material impact on the Company’s condensed consolidated financial statements.

Note 3—Revenue

Disaggregation of Revenue

See “Note 9—Segment and Geographical Information” for the Company’s revenue disaggregated by type of service and geographic area.

Remaining Performance Obligations

As of ~~September 30, 2022,~~March 31, 2023, the Company had ~~approximately $32.7~~$32.9 million of remaining performance obligations. The Company’s remaining performance obligations primarily consist of the transaction price that has been allocated to unexercised material rights related to the Company’s arrangements with talent subject to tiered service fees. The remaining transaction price allocated to other performance obligations is immaterial. As of ~~September 30, 2022,~~March 31, 2023, the Company expects to recognize ~~approximately $24.9~~$25.6 million over the next 12 months, with the remaining balance recognized thereafter.

The Company has applied the practical expedients and exemptions and does not disclose the value of remaining performance obligations for: (i) contracts with an original expected length of one year or less; and (ii) contracts for which the variable consideration is allocated entirely to a wholly unsatisfied promise to transfer a distinct service that forms part of a single performance obligation under the series guidance.

Contract Balances

The following table provides information about the balances of the Company’s trade and client receivables, net of allowance and contract liabilities included in deferred revenue and other liabilities, noncurrent:


(In thousands)	(In thousands)	September 30, 2022		December 31, 2021		(In thousands)	March 31, 2023		December 31, 2022
Trade and client receivables, net of allowance	Trade and client receivables, net of allowance	$	67,070	$	66,826	Trade and client receivables, net of allowance	$	59,291	$	64,888
Contract liabilities	Contract liabilities					Contract liabilities
Deferred revenue	Deferred revenue	24,910		22,083		Deferred revenue	25,557		25,075
Deferred revenue (component of other liabilities, noncurrent)	Deferred revenue (component of other liabilities, noncurrent)	7,807		6,349		Deferred revenue (component of other liabilities, noncurrent)	7,380		7,614

During the three ~~and nine~~ months ended ~~September 30, 2022,~~March 31, 2023, changes in the contract liabilities balances were a result of normal business activity and deferral, and subsequent recognition, of revenue related to arrangements with talent subject to tiered service fees and related allocation of transaction price to material rights.

Revenue recognized during the three ~~and nine~~ months ended ~~September 30,~~March 31, 2023 that was included in deferred revenue as of December 31, 2022 was $9.1 million. Revenue recognized during the three months ended March 31, 2022 that was included in deferred revenue as of ~~June 30, 2022 and~~ December 31, 2021 wa~~s $7.0 million and $16.6 million, respectively. Revenue recognized during the three and nine months ended September 30, 2021 that~~ was ~~included in deferred revenue as of June 30, 2021 and December 31, 2020 was $6.6 million and $14.0 million, respectively.~~$7.7 million.

Note 4—Fair Value Measurements

The Company defines fair value as the exchange price that would be received from the sale of an asset or paid to transfer a liability in the principal or most advantageous market for the asset or liability in an

orderly transaction between market participants on the measurement date. Valuation techniques used to measure fair value must maximize the use of observable inputs and minimize the use of unobservable inputs. The authoritative guidance describes three levels of inputs that may be used to measure fair value:

•Level I—Observable inputs that reflect unadjusted quoted prices for identical assets or liabilities in active markets;

•Level II—Observable inputs other than Level I prices, such as unadjusted quoted prices for similar assets or liabilities in active markets, unadjusted quoted prices for identical or similar assets or liabilities in markets that are not active, or other inputs that are observable or can be corroborated by observable market data for substantially the full term of the assets or liabilities; and

•Level III—Unobservable inputs that are supported by little or no market activity and that are significant to the fair value of the assets or liabilities. These inputs are based on the Company’s own assumptions used to measure assets and liabilities at fair value and require significant management judgment or estimation.

The categorization of a financial instrument within the fair value hierarchy is based upon the lowest level of input that is significant to its fair value measurement. The Company’s assessment of the significance of a particular input to the fair value measurement in its entirety requires management to make judgments and consider factors specific to the assets or liabilities.

The Company’s financial instruments that are carried at fair value consist of Level I and Level II assets as of ~~September 30, 2022~~March 31, 2023 and December 31, ~~2021.~~2022. The following tables ~~set forth~~summarize the ~~fair value of the~~Company’s cash and available-for-sale marketable securities’ amortized cost, gross unrealized gains, gross unrealized losses,

~~Company’s financial assets measured at~~and fair value ~~on a recurring basis based on the three-tier fair value hierarchy:~~by significant investment category reported as cash and cash equivalents or marketable securities as of March 31, 2023 and December 31, 2022:


(In thousands) September 30, 2022		Amortized Cost		Unrealized Gain		Unrealized Loss		Fair Value		Cash and Cash Equivalents		Marketable Securities
(In thousands) March 31, 2023														(In thousands) March 31, 2023	Amortized Cost		Unrealized Gain		Unrealized Loss		Fair Value		Cash and Cash Equivalents		Marketable Securities
Cash	Cash	$	27,725	$	—	$	—	$	27,725	$	27,725	$	—	Cash	$	38,551	$	—	$	—	$	38,551	$	38,551	$	—
Level I	Level I													Level I
Money market funds	Money market funds	92,163		—		—		92,163		92,163		—		Money market funds	53,522		—		—		53,522		53,522		—
Treasury bills	Treasury bills	188,803		8		(388)		188,423		34,901		153,522		Treasury bills	175,273		51		(5)		175,319		9,912		165,407
U.S. government securities	U.S. government securities	120,652		—		(2,647)		118,005		—		118,005		U.S. government securities	73,256		19		(955)		72,320		—		72,320
Total Level I	Total Level I	401,618		8		(3,035)		398,591		127,064		271,527		Total Level I	302,051		70		(960)		301,161		63,434		237,727
Level II	Level II													Level II
Commercial paper	Commercial paper	60,773		—		—		60,773		—		60,773		Commercial paper	64,914		—		—		64,914		—		64,914
Corporate bonds	Corporate bonds	115,170		2		(1,191)		113,981		1,634		112,347		Corporate bonds	30,682		8		(139)		30,551		—		30,551
Commercial deposits	Commercial deposits	32,130		—		—		32,130		—		32,130		Commercial deposits	19,880		—		—		19,880		—		19,880
Asset-backed securities	Asset-backed securities	28,658		—		(338)		28,320		—		28,320		Asset-backed securities	35,776		103		(207)		35,672		—		35,672
Yankee bonds	Yankee bonds	8,863		—		(43)		8,820		—		8,820		Yankee bonds	2,091		—		(4)		2,087		—		2,087
Agency bonds	Agency bonds	2,475		1		—		2,476		—		2,476		Agency bonds	5,977		2		(9)		5,970		—		5,970
Supranational bonds		2,997		—		(7)		2,990		—		2,990
Agency discount bonds														Agency discount bonds	10,829		13		—		10,842				10,842

Total Level II	Total Level II	251,066		3		(1,579)		249,490		1,634		247,856		Total Level II	170,149		126		(359)		169,916		—		169,916
Total	Total	$	680,409	$	11	$	(4,614)	$	675,806	$	156,423	$	519,383	Total	$	510,751	$	196	$	(1,319)	$	509,628	$	101,985	$	407,643


(In thousands) December 31, 2021		Amortized Cost		Unrealized Gain		Unrealized Loss		Fair Value		Cash and Cash Equivalents		Marketable Securities
(In thousands) December 31, 2022														(In thousands) December 31, 2022	Amortized Cost		Unrealized Gain		Unrealized Loss		Fair Value		Cash and Cash Equivalents		Marketable Securities
Cash	Cash	$	16,596	$	—	$	—	$	16,596	$	16,596	$	—	Cash	$	27,528	$	—	$	—	$	27,528	$	27,528	$	—
Level I	Level I													Level I
Money market funds	Money market funds	108,204		—		—		108,204		108,204		—		Money market funds	85,302		—		—		85,302		85,302		—
Treasury bills	Treasury bills	89,992		1		—		89,993		15,000		74,993		Treasury bills	172,500		13		(131)		172,382		5,096		167,286
U.S. government securities	U.S. government securities	94,839		—		(285)		94,554		—		94,554		U.S. government securities	106,167		—		(2,025)		104,142		—		104,142
Total Level I	Total Level I	293,035		1		(285)		292,751		123,204		169,547		Total Level I	363,969		13		(2,156)		361,826		90,398		271,428
Level II	Level II													Level II
Commercial paper	Commercial paper	171,918		—		—		171,918		29,544		142,374		Commercial paper	120,360		—		—		120,360		8,038		112,322
Corporate bonds	Corporate bonds	183,303		1		(217)		183,087		17,861		165,226		Corporate bonds	85,639		3		(639)		85,003		3,420		81,583

Commercial deposits														Commercial deposits	28,945		—		—		28,945		—		28,945
Asset-backed securities	Asset-backed securities	13,749		—		(11)		13,738		—		13,738		Asset-backed securities	33,261		31		(306)		32,986		—		32,986
Yankee bonds	Yankee bonds	6,693		—		(12)		6,681		—		6,681		Yankee bonds	5,176		—		(8)		5,168		—		5,168
Agency bonds														Agency bonds	12,989		7		(23)		12,973		—		12,973
Agency discount bonds														Agency discount bonds	8,796		31		—		8,827		—		8,827
Supranational bonds														Supranational bonds	3,000		—		(2)		2,998		—		2,998
Total Level II	Total Level II	375,663		1		(240)		375,424		47,405		328,019		Total Level II	298,166		72		(978)		297,260		11,458		285,802
Total	Total	$	685,294	$	2	$	(525)	$	684,771	$	187,205	$	497,566	Total	$	689,663	$	85	$	(3,134)	$	686,614	$	129,384	$	557,230

Unrealized Investment Losses

The following ~~table summarizes,~~tables summarize, for all debt securities classified as available for sale in an unrealized loss position as of ~~September 30,~~March 31, 2023 and December 31, 2022, the aggregate fair value and gross unrealized loss by the length of time those securities have been continuously in an unrealized loss position. ~~Unrealized losses as of December 31, 2021 were immaterial.~~


(In thousands)	(In thousands)	Less Than 12 Months				12 Months or Longer				Total				(In thousands)	Less Than 12 Months				12 Months or Longer				Total
Duration of unrealized losses		Fair Value		Unrealized loss		Fair Value		Unrealized loss		Fair Value		Unrealized loss
Money market funds		$	92,163	$	—	$	—	$	—	$	92,163	$	—
Commercial paper		60,773		—		—		—		60,773		—
Duration of unrealized losses March 31, 2023														Duration of unrealized losses March 31, 2023	Fair Value		Unrealized loss		Fair Value		Unrealized loss		Fair Value		Unrealized loss

Treasury bills	Treasury bills	141,722		(388)		—		—		141,722		(388)		Treasury bills	$	4,980	$	(5)	$	—	$	—	$	4,980	$	(5)
U.S. government securities	U.S. government securities	108,317		(2,343)		9,688		(304)		118,005		(2,647)		U.S. government securities	5,036		(5)		58,990		(950)		64,026		(955)
Corporate bonds	Corporate bonds	101,508		(1,006)		8,940		(185)		110,448		(1,191)		Corporate bonds	8,065		(46)		16,548		(93)		24,613		(139)
Asset-backed securities	Asset-backed securities	27,381		(328)		939		(10)		28,320		(338)		Asset-backed securities	24,341		(127)		5,088		(80)		29,429		(207)
Yankee bonds	Yankee bonds	8,820		(43)		—		—		8,820		(43)		Yankee bonds	2,087		(4)		—		—		2,087		(4)
Commercial deposits		2,397		—		—		—		2,397		—

Supranational bonds		2,990		(7)		—		—		2,990		(7)
Agency bonds														Agency bonds	2,479		(9)		—		—		2,479		(9)

Total	Total	$	546,071	$	(4,115)	$	19,567	$	(499)	$	565,638	$	(4,614)	Total	$	46,988	$	(196)	$	80,626	$	(1,123)	$	127,614	$	(1,319)


(In thousands)	Less Than 12 Months				12 Months or Longer				Total
Duration of unrealized losses December 31, 2022	Fair Value		Unrealized loss		Fair Value		Unrealized loss		Fair Value		Unrealized loss
Treasury bills	$	132,995	$	(131)	$	—	$	—	$	132,995	$	(131)
U.S. government securities	21,214		(63)		82,927		(1,963)		104,141		(2,026)
Corporate bonds	18,274		(120)		58,235		(519)		76,509		(639)
Asset-backed securities	23,515		(285)		1,707		(20)		25,222		(305)
Yankee bonds	2,578		(6)		2,591		(2)		5,169		(8)
Agency bonds	9,478		(23)		—		—		9,478		(23)
Supranational bonds	2,998		(2)		—		—		2,998		(2)
Total	$	211,052	$	(630)	$	145,460	$	(2,504)	$	356,512	$	(3,134)

For available-for-sale marketable debt securities with unrealized loss positions, the Company does not intend to sell these securities, and it is not more likely than not that the Company will be required to sell the securities. As of ~~September 30, 2022~~March 31, 2023 and December 31, ~~2021,~~2022, the decline in fair value of these securities was due to increases in interest rates and not due to ~~credit related~~credit-related factors. As of ~~September 30,~~March 31, 2023 and 2022, ~~and 2021,~~ the Company considered any decreases in market value to be temporary in nature and

did not consider any of the Company’s marketable securities to be other-than-temporarily impaired. ~~As such, the~~The Company did not record any impairment charges with respect to its marketable securities during each of the three ~~and nine~~ months ended ~~September 30, 2022~~March 31, 2023 and ~~2021.~~2022.

In March 2023, the Company sold $138.2 million of available-for-sale marketable securities to enable the repurchase of a portion of the Company’s outstanding 0.25% convertible senior notes due 2026, which are referred to as the Notes. For additional information regarding the Notes, refer to “Note 7—Debt.”

Note 5—Balance Sheet Components

Cash and Cash Equivalents, Restricted Cash, and Funds Held In Escrow, Including Funds In Transit

The following table reconciles cash and cash equivalents, restricted cash, and funds held in escrow that are restricted as reported in the condensed consolidated balance sheets as of March 31, 2023 and December 31, 2022 to the total of the same amounts shown in the condensed consolidated ~~statements~~statement of cash flows ~~as of September 30, 2022 and December~~for the three months ended March 31, ~~2021:~~2023:


(In thousands)	(In thousands)	September 30, 2022		December 31, 2021		(In thousands)	March 31, 2023		December 31, 2022
Cash and cash equivalents	Cash and cash equivalents	$	156,423	$	187,205	Cash and cash equivalents	$	101,985	$	129,384
Restricted cash	Restricted cash	4,290		4,040		Restricted cash	5,230		4,390
Funds held in escrow, including funds in transit	Funds held in escrow, including funds in transit	169,966		160,813		Funds held in escrow, including funds in transit	179,420		161,457
Total cash, cash equivalents, and restricted cash as shown in the condensed consolidated statement of cash flows	Total cash, cash equivalents, and restricted cash as shown in the condensed consolidated statement of cash flows	$	330,679	$	352,058	Total cash, cash equivalents, and restricted cash as shown in the condensed consolidated statement of cash flows	$	286,635	$	295,231

Property and Equipment, Net

Property and equipment, net consisted of the following:


(In thousands)	(In thousands)	September 30, 2022		December 31, 2021		(In thousands)	March 31, 2023		December 31, 2022
Computer equipment and software		$	6,370	$	5,493
Internal-use software and platform development	Internal-use software and platform development	30,926		25,738		Internal-use software and platform development	$	36,120	$	33,273
Leasehold improvements	Leasehold improvements	11,644		11,644		Leasehold improvements	11,644		11,644
Computer equipment and software						Computer equipment and software	6,705		6,514
Office furniture and fixtures	Office furniture and fixtures	3,365		3,365		Office furniture and fixtures	3,475		3,475
Total property and equipment	Total property and equipment	52,305		46,240		Total property and equipment	57,944		54,906
Less: accumulated depreciation	Less: accumulated depreciation	(30,818)		(24,911)		Less: accumulated depreciation	(34,840)		(32,843)
Property and equipment, net	Property and equipment, net	$	21,487	$	21,329	Property and equipment, net	$	23,104	$	22,063

For ~~each of~~ the three months ended ~~September 30,~~March 31, 2023 and 2022, ~~and 2021,~~ depreciation expense related to property and equipment was $0.8 ~~million. For the nine months ended September 30, 2022 and 2021, depreciation expense related to property and equipment was $2.4~~ million and ~~$2.8~~$0.8 million, respectively.

For the three months ended ~~September 30,~~March 31, 2023 and 2022, ~~and 2021,~~ the Company capitalized ~~$2.3~~$2.9 million and ~~$0.7 million of internal-use software and platform development costs, respectively. For the nine months ended September 30, 2022 and 2021, the Company capitalized $5.2 million and $4.1~~$1.2 million of internal-use software and platform development costs, respectively.

For the three months ended ~~September 30,~~March 31, 2023 and 2022, ~~and 2021,~~ amortization expense related to the capitalized internal-use software and platform development costs was $1.2 million and ~~$1.6~~$1.2 million, respectively. For the nine months ended September 30, 2022 and 2021, amortization expense related to the capitalized internal-use software and platform development costs was $3.6 million and $4.7 million, respectively.

Accrued Expenses and Other Current Liabilities

Accrued expenses and other current liabilities consisted of the following:


(In thousands)	(In thousands)	September 30, 2022		December 31, 2021		(In thousands)	March 31, 2023		December 31, 2022
Accrued compensation and related benefits	Accrued compensation and related benefits	$	13,703	$	23,047	Accrued compensation and related benefits	$	7,981	$	17,239
Accrued indirect taxes						Accrued indirect taxes	12,042		14,102
Accrued vendor expenses	Accrued vendor expenses	13,295		7,728		Accrued vendor expenses	15,271		8,858
Operating lease liability, current	Operating lease liability, current	6,455		6,315		Operating lease liability, current	6,547		6,502
Accrued indirect taxes		12,470		4,137
Accrued payment processing fees	Accrued payment processing fees	2,446		2,085		Accrued payment processing fees	2,485		2,425
Accrued talent costs	Accrued talent costs	1,886		1,417		Accrued talent costs	1,457		2,352
Other	Other	1,526		1,013		Other	1,812		2,133
Total accrued expenses and other current liabilities	Total accrued expenses and other current liabilities	$	51,781	$	45,742	Total accrued expenses and other current liabilities	$	47,595	$	53,611

Note 6—Commitments and Contingencies

Letters of Credit

In conjunction with the Company’s operating lease agreements, as of ~~September 30, 2022~~March 31, 2023 and December 31, ~~2021,~~2022, the Company had ~~three~~ irrevocable letters of credit outstanding in the aggregate ~~amount~~amounts of $1.7 million and $0.8 ~~million.~~million, respectively. The letters of credit are collateralized by restricted cash in the same amount. No amounts had been drawn against these letters of credit as of ~~September 30, 2022~~March 31, 2023 and December 31, ~~2021.~~2022.

Contingencies

The Company accrues contingent liabilities when it is probable that future expenditures will be made and such expenditures can be reasonably estimated. Potential contingencies may include various claims and litigation or non-income tax matters that arise from time to time in the normal course of business. Due to uncertainties inherent in such contingencies, the Company can give no assurance that it will prevail in any such matters, which could subject the Company to significant liability or damages. Any claims, litigation, or other contingencies could have an adverse effect on the Company’s business, financial position, results of operations, or cash flows in or following the period that claims, litigation, or other contingencies are resolved.

As of ~~September 30, 2022~~March 31, 2023 and December 31, ~~2021,~~2022, the Company was not a party to any material legal proceedings or claims, nor is the Company aware of any pending or threatened litigation or claims, including non-income tax matters, that could reasonably be expected to have a material adverse effect on its business, operating results, cash flows, or financial condition. Accordingly, the amounts accrued for contingencies for which the Company believes a loss is probable were not material as of ~~September 30, 2022~~March 31, 2023 and December 31, ~~2021.~~2022.

Indemnification

The Company has indemnification agreements with its officers, directors, and certain key employees to indemnify them while they are serving in good faith in their respective positions. In the ordinary course of business, the Company enters into contractual arrangements under which it agrees to provide indemnification of varying scope and terms to clients, business partners, vendors, and other parties, including, but not limited to, losses arising out of the Company’s breach of such agreements, claims related to potential data or information security breaches, intellectual property infringement claims made by third parties, and other liabilities relating to or arising from the Company’s products and services or its acts or omissions. In addition, subject to the terms of the applicable agreement, as part of the Company’s Upwork Enterprise and certain other premium offerings, the Company indemnifies clients that subscribe to worker classification services for losses arising from worker misclassification. It is not possible to determine the maximum potential loss under these indemnification provisions due to the Company’s

limited history of prior indemnification claims and the facts and circumstances involved in each particular provision.

Note 7—Debt

The following table presents the carrying value of the Company’s debt obligations as of ~~September 30, 2022~~March 31, 2023 and December 31, ~~2021:~~2022:


(In thousands)	(In thousands)	September 30, 2022			December 31, 2021			(In thousands)	March 31, 2023			December 31, 2022
Convertible senior notes	Convertible senior notes	$	575,000		$	575,000		Convertible senior notes	$	360,998		$	575,000
Total debt								Total debt	360,998			575,000
Less: unamortized debt issuance costs								Less: unamortized debt issuance costs	(6,293)			(10,739)

Less: unamortized debt issuance costs		(11,480)			(13,701)
Balance		563,520			561,299
Debt, current		—			—
Debt, noncurrent	Debt, noncurrent	$	563,520		$	561,299		Debt, noncurrent	$	354,705		$	564,261
Weighted-average interest rate	Weighted-average interest rate	0.77		%	0.76		%	Weighted-average interest rate	0.76		%	0.76		%

Convertible Senior Notes Due 2026

On August 10, 2021, the Company issued, at par value, $575.0 million aggregate principal amount of ~~0.25% convertible senior notes due 2026, which are referred to as~~ the Notes. The issuance included the full exercise of an option granted by the Company to the initial purchasers of the Notes to purchase an additional $75.0 million aggregate principal amount of Notes. The Notes were issued pursuant to and are subject to the terms and conditions of an indenture ~~which is referred to as the Indenture,~~ between the Company and Wells Fargo Bank, National Association, as ~~trustee.~~ trustee, which is referred to as the Indenture.

The Notes were offered and sold in a private offering to qualified institutional buyers pursuant to Rule 144A under the Securities Act of 1933, as amended.

On each of March 21, 2023 and March 23, 2023, the Company entered into separate, privately negotiated repurchase agreements with a limited number of institutional holders of the Notes to repurchase for cash an aggregate of $214.0 million principal amount of the Notes, which are collectively referred to as the Repurchases. The Company paid $170.8 million in cash to consummate the Repurchases. As a result, during the three months ended March 31, 2023, the Company recognized a gain on the early extinguishment of debt of $38.9 million, which is net of $3.7 million related to the pro-rata write-off of unamortized issuance costs associated with the sale of the Notes in August 2021, and $0.6 million of other fees incurred to effect the Repurchases. The resulting gain on early extinguishment of debt is included in other income, net in the Company’s condensed consolidated statement of operations and comprehensive income (loss). As of March 31, 2023, $361.0 million principal amount of the Notes remain outstanding.

The Notes are senior, unsecured obligations of the Company and bear interest at a rate of 0.25% per year. Interest will accrue from August 10, 2021 and is payable semiannually in arrears on February 15 and August 15 of each year, beginning on February 15, 2022, and the principal amount of the Notes will not accrete. The Notes will mature on August 15, 2026, unless earlier redeemed, repurchased, or converted in accordance with the terms of the Notes.

Holders may convert all or any portion of their Notes, in multiples of $1,000 principal amount at the option of the holder (i) on or after May 15, 2026, at any time until the close of business on the second scheduled trading day immediately preceding the maturity date, and (ii) prior to the close of business on the business day immediately preceding May 15, 2026, only upon satisfaction of certain conditions and during certain periods specified as follows:

•during any calendar quarter commencing after the calendar quarter ending on December 31, 2021, if the last reported sale price of the Company’s common stock is greater than or equal to 130% of the conversion price for at least 20 trading days (whether or not consecutive) during a period of 30 consecutive trading days ending on, and including, the last trading day of the immediately preceding calendar quarter of the conversion price on each applicable trading day;

•during the five consecutive business day period after any five consecutive trading day period, which is referred to as the Measurement Period, in which the trading price (as defined in the Indenture) per $1,000 principal amount of Notes for each trading day of the Measurement Period was less than 98% of the product of the last reported sale price per share of the Company’s common stock on such trading day and the conversion rate on such trading day;

•if the Company calls such Notes for redemption, at any time prior to the close of business on the second scheduled trading day immediately preceding the redemption date; and

•upon the occurrence of specified corporate events described in the Indenture.

Upon conversion, the Notes may be settled in shares of the Company’s common stock, cash or a combination of cash and shares of the common stock, at the election of the Company. The Notes have an

initial conversion rate of 15.1338 shares of common stock per $1,000 principal amount of Notes, which is subject to adjustment in certain circumstances. This is equivalent to an initial conversion price of approximately $66.08 per share of the Company’s common stock. The conversion rate is subject to customary adjustments under certain circumstances in accordance with the terms of the Indenture. In addition, if certain corporate events that constitute a make-whole fundamental change (as defined in the Indenture) occur or if the Company issues a notice of redemption with respect to the Notes prior to the maturity date, then the conversion rate will, in certain circumstances, be increased for a specified period of time.

The Company may redeem for cash all or any portion of the Notes (subject to a partial redemption limitation), at the Company’s option, on or after August 20, 2024, if the last reported sale price per share of the Company’s common stock has been at least 130% of the conversion price then in effect for at least

20 trading days (whether or not consecutive) during any 30 consecutive trading day period (including the last trading day of such period) ending on, and including, the trading day immediately preceding the date on which the Company provides notice of redemption at a redemption price equal to 100% of the principal amount of the Notes to be redeemed, plus any accrued and unpaid interest, if any, to, but excluding, the redemption date. No sinking fund is provided for the Notes, which means that the Company is not required to redeem or retire the Notes periodically.

Upon the occurrence of a fundamental change (as defined in the Indenture), subject to certain conditions, holders have the right to require the Company to repurchase for cash all or a portion of their Notes at a price equal to 100% of the principal amount of the Notes to be repurchased, plus any accrued and unpaid interest thereon, if any, until, but excluding, the fundamental change repurchase date.

The Notes are the Company’s senior unsecured obligations and rank senior in right of payment to any of the Company’s existing and future indebtedness that is expressly subordinated in right of payment to the Notes; equal in right of payment to any of the Company’s existing and future unsecured indebtedness that is not so subordinated; effectively junior in right of payment to any of the Company’s existing and future secured indebtedness to the extent of the value of the assets securing such indebtedness; and structurally junior to all existing and future indebtedness and other liabilities (including trade payables) of the Company’s subsidiaries.

The net proceeds from the issuance of the Notes were approximately $560.1 million, after deducting debt issuance costs. The total debt issuance costs incurred and recorded by the Company amounted to $14.9 million, which were recorded as a reduction to the face amount of the Notes and will be amortized to interest expense on a straight-line basis, which produces a materially consistent amount as the effective interest method over the contractual term of the Notes.

For the three months ended ~~September 30, 2022,~~March 31, 2023, interest expense was $0.4 million and amortization of the issuance costs was $0.7 million related to the Notes. For the ~~nine~~three months ended ~~September 30,~~March 31, 2022, interest expense was ~~$1.1~~$0.4 million and amortization of the issuance costs was ~~$2.2~~$0.7 million related to the Notes. ~~For the three and nine months ended September 30, 2021, interest expense related to the Notes and amortization of the issuance costs was $0.6 million.~~ As of ~~September 30, 2022,~~March 31, 2023, the if-converted value of the Notes did not exceed the outstanding principal amount. As of ~~September 30, 2022,~~March 31, 2023, the total estimated fair value of the Notes was ~~$425.0~~$304.1 million and was determined based on a market approach using actual bids and offers of the Notes in an over-the-counter market on the last trading day of the period. The Company considers these assumptions to be Level II inputs in accordance with the fair value hierarchy described in “Note 4—Fair Value Measurements.”

Capped Calls

In connection with the pricing of the Notes on August 5, 2021 and in connection with the full exercise by the initial purchasers on August 9, 2021 of their option to purchase additional Notes, the Company used approximately $49.4 million of the net proceeds from the issuance of the Notes to enter into privately negotiated capped call transactions, which are referred to as the Capped Calls, with various financial institutions.

Subject to customary anti-dilution adjustments substantially similar to those applicable to the Notes, the Capped Calls cover the number of shares of the Company’s common stock initially underlying the Notes. By entering into the Capped Calls, the Company expects to reduce the potential dilution to its common stock (or, in the event a conversion of the Notes is settled in cash, to reduce its cash payment obligation) in the event that at the time of conversion of the Notes its common stock price per share exceeds the conversion price of the Notes, with such reduction subject to a cap based on the cap price. If, however, the market price per share of common stock, as measured under the terms of the Capped Calls, exceeds the cap price of the Capped Calls, there would be dilution and/or there would not be an offset of such potential cash payments, in each case, to the extent that the then-market price per share of common stock exceeds the cap price of the Capped Calls. The initial cap price of the Capped Calls is $92.74 per share of common stock, which represents a premium of 100% over the last reported sale price of the common stock of $46.37 per share on August 5, 2021, and is subject to certain customary adjustments under the terms of the Capped Calls; provided that the cap price will not be reduced to an amount less than the strike price of $66.08 per share.

The Capped Calls are separate transactions and are not part of the terms of the Notes. The Capped Calls meet the criteria for classification as equity and, as such, are not remeasured each reporting period and are included as a reduction to additional paid-in-capital within stockholders’ equity.

The Capped Calls remain in effect notwithstanding the Repurchases.

Note 8—Net Loss per Share

The following table sets forth the computation of the Company’s basic and diluted net loss per share for the periods presented:


		Three Months Ended September 30,				Nine Months Ended September 30,					Three Months Ended March 31,
(In thousands, except share and per share data)	(In thousands, except share and per share data)	2022		2021		2022		2021		(In thousands, except share and per share data)	2023		2022
Numerator:
Net loss		$	(24,827)	$	(9,311)	$	(73,385)	$	(33,684)

Numerator:										Numerator:
Basic: net income (loss)										Basic: net income (loss)	$	17,167	$	(24,738)
Gain on early extinguishment of debt, net of tax										Gain on early extinguishment of debt, net of tax	(38,525)		—
Interest expense related to convertible senior notes, net of tax										Interest expense related to convertible senior notes, net of tax	389		—
Diluted										Diluted	$	(20,969)	$	(24,738)

Denominator:	Denominator:									Denominator:
Weighted-average shares used to compute net loss per share, basic and diluted		130,830,411		127,914,696		130,082,683		126,651,490
Weighted-average shares used to compute net income (loss) per share, basic and diluted										Weighted-average shares used to compute net income (loss) per share, basic and diluted
Basic										Basic	132,835,837		129,358,872

Net loss per share, basic and diluted		$	(0.19)	$	(0.07)	$	(0.56)	$	(0.27)

Common stock issuable in connection with convertible senior notes										Common stock issuable in connection with convertible senior notes	3,130,578		—
Diluted										Diluted	135,966,415		129,358,872

Net income (loss) per share:										Net income (loss) per share:
Basic										Basic	$	0.13	$	(0.19)
Diluted										Diluted	$	(0.15)	$	(0.19)

The following potentially dilutive shares were excluded from the computation of diluted net loss per share because including them would have been anti-dilutive:


		As of September 30,			As of March 31,
		2022	2021		2023	2022
Options to purchase common stock	Options to purchase common stock	3,911,482	4,402,667	Options to purchase common stock	3,628,396	4,139,974
Common stock issuable upon exercise of common stock warrants	Common stock issuable upon exercise of common stock warrants	350,000	400,000	Common stock issuable upon exercise of common stock warrants	350,000	350,000
Common stock issuable upon vesting of restricted stock units		8,573,146	4,663,447
Common stock issuable upon vesting of restricted stock units and performance stock units				Common stock issuable upon vesting of restricted stock units and performance stock units	10,619,944	7,752,697
Common stock issuable in connection with employee stock purchase plan	Common stock issuable in connection with employee stock purchase plan	1,070,071	262,029	Common stock issuable in connection with employee stock purchase plan	1,236,008	300,130
Common stock issuable in connection with convertible senior notes	Common stock issuable in connection with convertible senior notes	8,701,935	8,701,935	Common stock issuable in connection with convertible senior notes	5,463,045	8,701,935
Total	Total	22,606,634	18,430,078	Total	21,297,393	21,244,736

Note 9—Segment and Geographical Information

The Company operates as one operating and reportable segment for purposes of allocating resources and evaluating financial performance.

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The following table sets forth total revenue by type of service for the periods presented:


		Three Months Ended September 30,				Nine Months Ended September 30,					Three Months Ended March 31,
(In thousands)	(In thousands)	2022		2021		2022		2021		(In thousands)	2023		2022
Marketplace	Marketplace									Marketplace
Basic, Plus, Client Marketplace(1) and other	Basic, Plus, Client Marketplace(1) and other	$	132,647	$	108,893	$	383,343	$	312,569	Basic, Plus, Client Marketplace(1) and other	$	136,676	$	118,667
Enterprise	Enterprise	12,496		8,890		35,550		24,344		Enterprise	11,412		10,758
Managed services	Managed services	13,498		10,358		37,983		29,028		Managed services	12,770		11,912
Total revenue	Total revenue	$	158,641	$	128,141	$	456,876	$	365,941	Total revenue	$	160,858	$	141,337

(1) In April 2022, the Company combined its Upwork Basic and Upwork Plus client offerings into a ~~new~~ Client Marketplace offering.

The Company generates its revenue from talent and clients. The following table sets forth total revenue by geographic area based on the billing address of its talent and clients for the periods presented:


		Three Months Ended September 30,				Nine Months Ended September 30,					Three Months Ended March 31,
(In thousands)	(In thousands)	2022		2021		2022		2021		(In thousands)	2023		2022
Talent	Talent									Talent
United States	United States	$	21,607	$	18,429	$	64,286	$	55,308	United States	$	22,460	$	20,763
India	India	11,337		11,109		34,764		31,430		India	11,428		11,421
Philippines	Philippines	9,981		8,602		29,668		23,668		Philippines	10,366		9,636
Rest of world		39,296		37,046		121,865		107,112
Total talent		82,221		75,186		250,583		217,518
Rest of world (1)										Rest of world (1)	41,402		40,823
Total talent revenue										Total talent revenue	85,656		82,643
Clients	Clients									Clients
United States	United States	56,897		39,661		153,369		110,275		United States	55,451		43,839
Rest of world		19,523		13,294		52,924		38,148
Total clients		76,420		52,955		206,293		148,423
Rest of world (1)										Rest of world (1)	19,751		14,855
Total clients revenue										Total clients revenue	75,202		58,694
Total revenue	Total revenue	$	158,641	$	128,141	$	456,876	$	365,941	Total revenue	$	160,858	$	141,337

(1) During the three months ended March 31, 2023 and 2022, no single country included in the Rest of world category had revenue that exceeded 10% of Total talent revenue, Total clients revenue, or Total revenue.

Substantially all of the Company’s long-lived assets were located in the United States as of ~~September 30, 2022~~March 31, 2023 and December 31, ~~2021.~~2022.

Note 10—Subsequent Events

On May 3, 2023, the Company announced a reduction to its workforce. As a result, the Company expects to incur charges of approximately $4.0 million, consisting primarily of employee severance and benefit costs, in the second quarter of 2023.

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Item 2. Management’s Discussion and Analysis of Financial Condition and Results of Operations.

You should read the following discussion and analysis of our financial condition and results of operations together with the section titled “Risk Factors” and the condensed consolidated financial statements and related notes included elsewhere in this Quarterly Report. This discussion contains forward-looking statements based upon current expectations that involve risks and uncertainties, as well as assumptions that may never materialize or that may be proven incorrect. Our actual results may differ materially from those anticipated in these forward-looking statements as a result of various factors, including those discussed in the sections titled “Special Note Regarding Forward-Looking Statements” and “Risk Factors,” and in other parts of this Quarterly Report.

Overview

Independent talent is an increasingly sought-after, critical, and expanding segment of the global workforce. 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 GSV. 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. We define talent as users that advertise and provide services to clients through our work marketplace, and we define clients as users that seek and work with talent through our work marketplace. Talent includes independent professionals and agencies of varying sizes. ~~The clients~~Clients on our work marketplace range in size, ~~from~~including small businesses to Fortune 100 companies.

~~Recent Events~~Financial Highlights

In ~~April~~the first quarter of 2023, we continued to focus on evolving our products and offerings and driving brand awareness through marketing efforts. The number of active clients increased 4% as of March 31, 2023, as compared to the same period in 2022, ~~we combined~~and our ~~Upwork Basic and Plus~~GSV per active client ~~offerings into~~increased 5% as of March 31, 2023, as compared to the same period in 2022. Our first quarter results were impacted by a number of factors, including changes to client fees as a result of the shift to our ~~new~~ Client Marketplace offering in April 2022 and challenging macroeconomic conditions. As a result, GSV remained flat at $1.0 billion during the three months ended March 31, 2023, as compared to the same period in 2022.

For the three months ended March 31, 2023, marketplace revenue increased 14%, as compared to the same period in 2022, driven by client fee changes related to the shift to our Client Marketplace offering in April 2022. Additionally, we continued our efforts to better address large enterprise and other clients through our Upwork Enterprise and other premium offerings. As a result, for the three months ended March 31, 2023, Enterprise Revenue increased 6%, as compared to the same period in 2022, which ~~simplifies~~also drove the increase in marketplace revenue.

Recent Developments

In March 2023, we announced the retirement of our ~~pricing~~tiered service fee structure for talent working with clients on our Client Marketplace offering—ranging from 5% to 20%—in favor of a flat fee of 10%. This change will take effect on new contracts and existing contracts that would have otherwise been subject to a 20% fee under our tiered service fee model starting May 3, 2023. Talent that have existing contracts with a 5% fee under our tiered service fee model will retain that rate for those contracts through the end of 2023. Additionally, a contract initiation fee for clients ~~of those offerings. This model makes available the most popular features of the legacy Upwork Plus offering, while eliminating the monthly client subscription fees and moving~~on our Client Marketplace offering—up to $4.95 per contract—was introduced for all contracts on April 26, 2023. As a ~~client~~result, we expect marketplace ~~fee of 5% on each transaction—or 3% if paid via ACH for eligible clients. This pricing change resulted in greater~~ revenue and ~~a higher~~ marketplace take rate ~~but also drove some reduction in client spend.~~ to increase throughout the remainder of 2023.

Additionally, in light of the ~~third quarter, we experienced seasonal and challenging~~worsening macroeconomic conditions ~~that were initially observed~~as well as our efforts to reduce spend and streamline operations, we implemented a reduction of our workforce in May 2023, largely in our sales team. We reduced our total number of full-time employees by approximately 15% and have also reduced positions of independent team members. As a result, we expect to incur charges of approximately $4.0 million, consisting primarily of employee severance and benefit costs, in the second quarter of ~~2022. As~~2023. We are also implementing a ~~result~~number of ~~the pricing change and the seasonal and macroeconomic conditions, GSV decreased~~other cost-saving measures, including reducing our investments in ~~the third quarter, as compared to the second quarter of 2022.~~

In March 2022, we suspended business operations in Russia and Belarus, announcing that contracts with talent or clients in Russia or Belarus would be required to wind down by May 1, 2022. As anticipated, we saw a slightly smaller impact to revenue in the third quarter compared to the second quarter of 2022. Although the Russian war against Ukraine did not have a material adverse impact on our revenue or other financial results for the three and nine months ended September 30, 2022, at this time we are unable to fully assess the aggregate impact it will have on our business in future periods due to various uncertainties, which include, but are not limited to, the duration of the war, the ability of talent based in Ukraine to continue working, the war’s effect on the economy, its impact to the businesses of our clients, actions that may be taken by governmental authorities related to the war, and other factors identified in Part II, Item 1A, “Risk Factors” in this Quarterly Report, including the risk factor titled “Russia’s invasion of Ukraine and our decision to suspend our business operations in Russia and Belarus have affected and may continue to affect our business and results of operations.”

1718

brand awareness, vendor spend, and other non-personnel costs. We expect these measures will positively impact adjusted EBITDA for the full year 2023.

Key Financial and Operational Metrics

As of and for the three ~~and nine~~ months ended ~~September 30, 2022,~~March 31, 2023, our key financial and operating metrics are as follows:


		Three Months Ended September 30,						% Change		Nine Months Ended September 30,						% Change			Three Months Ended March 31,						% Change
(In thousands, except percentages)	(In thousands, except percentages)	2022			2021					2022			2021					(In thousands, except percentages)	2023			2022
GSV	GSV	$	1,027,325		$	903,989		14	%	$	3,074,713		$	2,566,572		20	%	GSV	$	1,003,345		$	1,001,375				—	%
Marketplace revenue	Marketplace revenue	$	145,143		$	117,783		23	%	$	418,893		$	336,913		24	%	Marketplace revenue	$	148,088		$	129,425		14	%
Marketplace take rate	Marketplace take rate	14.3		%	13.2		%	1.1	%	13.8		%	13.3		%	0.5	%	Marketplace take rate	14.9		%	13.1		%	1.8	%
Net loss		$	(24,827)		$	(9,311)		(167)	%	$	(73,385)		$	(33,684)		(118)	%
Net income (loss)																		Net income (loss)	$	17,167		$	(24,738)		169	%
Adjusted EBITDA1	Adjusted EBITDA1	$	(2,868)		$	8,216		(135)	%	$	(5,166)		$	22,396		(123)	%	Adjusted EBITDA1	$	(2,926)		$	(433)		(576)	%


		As of September 30,				% Change			As of March 31,				% Change
(Active clients are in thousands)	(Active clients are in thousands)	2022		2021				(Active clients are in thousands)	2023		2022
Active clients	Active clients	818		752		9	%	Active clients	827		793		4	%
GSV per active client	GSV per active client	$	4,958	$	4,375	13	%	GSV per active client	$	4,967	$	4,742	5	%

We monitor the following key financial and operational metrics to evaluate our business, measure our performance, identify trends affecting our business, formulate business plans, and make strategic decisions. For a discussion of limitations in the measurement of our key financial and operational metrics, see “Risk Factors—We track certain performance metrics with internal tools and do not independently verify such metrics. Certain of our performance metrics may not accurately reflect certain details of our business, are subject to inherent challenges in measurement, and real or perceived inaccuracies in such metrics may harm our reputation and negatively affect our business” in Part II, Item 1A of this Quarterly Report.

Gross Services Volume (GSV)

GSV includes both client spend and additional fees charged for other services. Client spend, which we define as the total amount that clients spend on both our marketplace offerings and our managed services offering, is the primary component of GSV. GSV also includes fees charged to ~~talent,~~users, such as for transacting payments through our work marketplace, user memberships, ~~and~~ purchases of “Connects” (virtual tokens that allow talent to bid on projects and paid promotional products on our work marketplace), and foreign currency exchange. GSV is an important metric because it represents the amount of business transacted through our work marketplace.

Marketplace Revenue

We generate marketplace revenue from both talent and clients. Marketplace revenue is primarily generated from fees charged to talent as a percentage of their billings to clients, which we refer to as

1Adjusted EBITDA is not prepared in accordance with, and is not an alternative to, financial measures prepared in accordance with U.S. GAAP. See “Key Financial and Operational Metrics—Non-GAAP Financial Measures” below for a definition of adjusted EBITDA and for information regarding our use of adjusted EBITDA and a reconciliation of adjusted EBITDA to net loss, the most directly comparable financial measure prepared under U.S. GAAP.

talent service fees, and to a lesser extent, fees charged to clients through our Client Marketplace offering, which we refer to as client marketplace fees. Additionally, marketplace revenue includes revenue from our Enterprise offering, which we refer to as Enterprise Revenue, including all client fees, subscriptions, and talent service fees. We also generate marketplace revenue from fees for premium offerings, including talent memberships, purchases of Connects, and other services, such as foreign currency exchange when clients choose to pay in currencies other than the U.S. dollar, and our Upwork Payroll offering.

In March 2023, we announced (i) the retirement of our tiered service fee structure for talent working with clients on our Client Marketplace offering—ranging from 5% to 20%—in favor of a flat fee of 10% and (ii) a contract initiation fee up to $4.95 per contract for clients on our Client Marketplace offering.

Marketplace Take Rate

Marketplace take rate measures the correlation between marketplace revenue and marketplace GSV and is calculated by dividing marketplace revenue by marketplace GSV. We define marketplace GSV as GSV derived from our marketplace offerings. Marketplace take rate is an important metric because it is the key indicator of how well we monetize spend on our work marketplace from our Client Marketplace (and previously Upwork Basic and Upwork Plus), Enterprise, Payroll, and other premium offerings, which we refer to as our marketplace offerings.

Active Clients and GSV per Active Client

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 on the date of measurement. We believe that the number of active clients and GSV per active client are indicators of the growth and overall health of our business. The number of active clients is a primary driver of GSV and, in turn, marketplace revenue.

~~Marketplace Revenue~~

Marketplace revenue, which represents the majority of our revenue, consists of revenue derived from our marketplace offerings. Marketplace offerings consist of all offerings other than our managed services offering, including our Upwork Basic, Plus, Client Marketplace, and Enterprise offerings. In April 2022, we combined our Upwork Basic and Plus client offerings into our new Client Marketplace offering, which simplifies our pricing model for clients of those offerings. This model makes available the most popular features of the legacy Upwork Plus offering, while eliminating the monthly client subscription fees and moving to a client marketplace fee of 5% on each transaction—or 3% if paid via ACH for eligible clients. We generate marketplace revenue from both talent and clients. Marketplace revenue is primarily comprised of talent service fees, and to a lesser extent, client marketplace fees (and prior to the launch of our Client Marketplace offering, payment processing and administration fees). Additionally, marketplace revenue includes revenue from our Enterprise offering, which we refer to as Enterprise Revenue, including all client fees, subscriptions, and talent service fees. We also generate marketplace revenue from fees for premium offerings, including talent memberships, purchases of Connects, and other services, such as foreign currency exchange when clients choose to pay in currencies other than the U.S. dollar, and our Upwork Payroll offering.

~~Marketplace Take Rate~~

Marketplace take rate measures the correlation between marketplace revenue and marketplace GSV and is calculated by dividing marketplace revenue by marketplace GSV. We define marketplace GSV as GSV derived from our marketplace offerings. Marketplace take rate is an important metric because it is the key indicator of how well we monetize spend on our work marketplace from our Client Marketplace (and previously Upwork Basic and Plus), Enterprise, Payroll, and other premium offerings, which we refer to as our marketplace offerings.

Non-GAAP Financial Measures

In addition to our results determined in accordance with U.S. GAAP, adjusted EBITDA is a non-GAAP measure that we believe is useful in evaluating our operating performance.

We define adjusted EBITDA as net income (loss) adjusted for stock-based compensation expense; depreciation and amortization; interest expense; other (income) expense, net; income tax (benefit) provision; and, if applicable, other non-cash transactions. Additionally, in response to Russia’s invasion of Ukraine, during the ~~nine~~three months ended ~~September 30,~~March 31, 2022, we incurred certain incremental expenses associated with our humanitarian response ~~efforts, and we may continue to incur such expenses as the war continues to unfold.~~efforts. These expenses are not representative of our ongoing operations, and, as a result, we excluded these costs from adjusted EBITDA for the ~~nine~~three months ended ~~September 30, 2022 and, to the extent we continue to incur these expenses, intend to continue to do so in future periods.~~March 31, 2022. Adjusted EBITDA is not prepared in accordance with, and is not an alternative to, financial measures prepared in accordance with U.S. GAAP.

1920

The following table presents a reconciliation of net loss, the most directly comparable financial measure prepared in accordance with U.S. GAAP, to adjusted EBITDA for each of the periods indicated:


		Three Months Ended September 30,				Nine Months Ended September 30,					Three Months Ended March 31,
(In thousands)	(In thousands)	2022		2021		2022		2021		(In thousands)	2023		2022
Net Loss		$	(24,827)	$	(9,311)	$	(73,385)	$	(33,684)
Net Income (loss)										Net Income (loss)	$	17,167	$	(24,738)
Add back (deduct):	Add back (deduct):									Add back (deduct):
Stock-based compensation expense	Stock-based compensation expense	20,404		13,906		56,119		38,666		Stock-based compensation expense	19,900		16,735
Depreciation and amortization		1,982		2,439		6,007		8,187
Depreciation										Depreciation	2,024		2,009
Interest expense	Interest expense	1,117		746		3,362		1,055		Interest expense	1,101		1,125
Other (income) expense, net		(1,772)		222		(2,215)		161
Other income, net (1)										Other income, net (1)	(44,101)		(68)
Income tax provision	Income tax provision	40		26		96		59		Income tax provision	795		29
Tides Foundation common stock warrant expense	Tides Foundation common stock warrant expense	188		188		563		563		Tides Foundation common stock warrant expense	188		188
Impairment expense		—		—		—		7,389

Humanitarian response efforts(2)	Humanitarian response efforts(2)	—		—		4,287		—		Humanitarian response efforts(2)	—		4,287
Adjusted EBITDA	Adjusted EBITDA	$	(2,868)	$	8,216	$	(5,166)	$	22,396	Adjusted EBITDA	$	(2,926)	$	(433)

(1) During the three months ended March 31, 2023, we recognized a gain on the early extinguishment of debt of $38.9 million, which is included in other income, net.

(2) Represents (i) $1.4 million of special one-time bonuses to our team members in the region impacted by Russia’s invasion of Ukraine, (ii) $1.5 million of expenses incurred in connection with the relocation of our team members in the impacted region, (iii) $1.1 million of donations made to humanitarian aid organizations to support initiatives related to humanitarian response efforts in the impacted region, primarily to Direct Relief International, a humanitarian aid organization, and (iv) $0.4 million of payments of one-time service award bonuses (and associated taxes) to certain of our team members paid in recognition of contributions made by such team members to our humanitarian response efforts in the impacted region.

We use adjusted EBITDA as a measure of operational efficiency. We believe that this non-GAAP financial measure is useful to investors for period-to-period comparisons of our business and in understanding and evaluating our operating results for the following reasons:

•adjusted EBITDA is widely used by investors and securities analysts to measure a company’s operating performance without regard to items such as stock-based compensation expense; depreciation and amortization; interest expense; other (income) expense, net; income tax (benefit) provision; and, if applicable, other non-cash transactions that can vary substantially from company to company depending upon their financing, capital structures, and the method by which assets were acquired;

•our management uses adjusted EBITDA in conjunction with financial measures prepared in accordance with U.S. GAAP for planning purposes, including the preparation of our annual operating budget, as a measure of our core operating results and the effectiveness of our business strategy, and in evaluating our financial performance; and

•adjusted EBITDA provides consistency and comparability with our past financial performance, facilitates period-to-period comparisons of our core operating results, and also facilitates comparisons with other peer companies, many of which use similar non-GAAP financial measures to supplement their U.S. GAAP results.

Our use of adjusted EBITDA has limitations as an analytical tool, and you should not consider it in isolation or as a substitute for analysis of our financial results as reported under U.S. GAAP. Some of these limitations are as follows:

•adjusted EBITDA excludes stock-based compensation expense, which has recently been, and will continue to be for the foreseeable future, a significant recurring expense for our business and an important part of our compensation strategy;

•although depreciation and amortization expense are non-cash charges, the assets being depreciated and amortized may have to be replaced in the future, and adjusted EBITDA does not reflect cash capital expenditure requirements for such replacements or for new capital expenditure requirements;

•adjusted EBITDA does not reflect: (a) changes in, or cash requirements for, our working capital needs; (b) interest expense, or the cash requirements necessary to service interest or principal

payments on our debt, which reduces cash available to us; or (c) tax payments that may represent a reduction in cash available to us; and

•other companies, including companies in our industry, may calculate adjusted EBITDA or similarly titled measures differently, which reduces the usefulness of this measure for comparative purposes.

Because of these and other limitations, you should consider adjusted EBITDA along with other financial performance measures, including net loss and our other financial results prepared in accordance with U.S. GAAP.

Components of Our Results of Operations

Marketplace Revenue

Marketplace revenue represents the majority of our revenue and is generated from our marketplace offerings. Under these marketplace offerings, we generate revenue from both talent and clients.

~~Client Marketplace Offering.~~ In April 2022, we combined our Upwork Basic and Plus client offerings into a new Client Marketplace offering, which simplifies our pricing model for clients of those offerings. This model makes available the most popular features of the previous Upwork Plus offering, while eliminating the monthly client subscription fees and moving to a client marketplace fee of 5% on each transaction—or 3% if payment is made via ACH for eligible clients.

Managed Services Revenue

Through our managed services offering, we are responsible for providing services and engaging talent directly or as employees of third-party staffing providers to perform services for clients on our behalf. Under U.S. GAAP, we are deemed to be the principal in these managed services arrangements and therefore recognize the entire GSV of managed services projects as managed services revenue, as compared to recognizing only the percentage of the client spend that we receive, as we do with our marketplace offerings.

Cost of Revenue

Cost of revenue consists primarily of the cost of payment processing fees, amounts paid to talent to deliver services for clients under our managed services offering, personnel-related costs for our services and support personnel, third-party hosting fees, and the amortization expense associated with capitalized internal-use software and platform development costs. We define personnel-related costs as salaries, bonuses, benefits, travel and entertainment, and stock-based compensation costs for employees and the costs related to other service providers we engage.

Research and Development

Research and development expense primarily consists of personnel-related ~~costs and third-party hosting costs related to development.~~costs. Research and development costs are expensed as incurred, except to the extent that such costs are associated with internal-use software and platform development that qualifies for capitalization.

Sales and Marketing

Sales and marketing expense consists primarily of expenses related to advertising and marketing activities, as well as personnel-related costs, including sales commissions, which we expense as they are ~~incurred, and advertising and marketing activities.~~incurred.

General and Administrative

General and administrative expense consists primarily of personnel-related costs for our executive, finance, legal, human resources, ~~corporate development,~~ and operations functions; outside consulting, legal, and accounting services; impairment expense; and insurance.

Provision for Transaction Losses

Provision for transaction losses consists primarily of losses resulting from fraud and bad debt expense ~~and fraud~~ associated with our trade and client receivables balance and transaction losses associated with chargebacks. Provisions for these items represent estimates of losses based on our actual historical incurred losses and other factors.

Interest Expense

Interest expense consists of interest on our outstanding borrowings.

Other ~~(Income) Expense,~~Income, Net

Other ~~(income) expense,~~income, net consists primarily of ~~gains and losses from foreign currency exchange transactions and~~ interest income that we earn from our deposits in money market funds and investments in marketable ~~securities.~~securities and gains and losses from foreign currency exchange transactions. Additionally, during the three months ended March 31, 2023, we recognized a gain on the early extinguishment of debt of $38.9 million, which is included in other income, net. For additional information about the gain on early extinguishment of debt, see the section below titled “—Convertible Senior Notes Due 2026.”

Results of Operations

The following table sets forth our condensed consolidated results of operations for the periods presented:


		Three Months Ended September 30,				Nine Months Ended September 30,					Three Months Ended March 31,
(In thousands)	(In thousands)	2022		2021		2022		2021		(In thousands)	2023		2022
Revenue	Revenue									Revenue
Marketplace	Marketplace	$	145,143	$	117,783	$	418,893	$	336,913	Marketplace	$	148,088	$	129,425
Managed services	Managed services	13,498		10,358		37,983		29,028		Managed services	12,770		11,912
Total revenue	Total revenue	158,641		128,141		456,876		365,941		Total revenue	160,858		141,337
Cost of revenue(1)	Cost of revenue(1)	40,470		34,933		119,243		98,457		Cost of revenue(1)	40,427		37,916
Gross profit	Gross profit	118,171		93,208		337,633		267,484		Gross profit	120,431		103,421
Operating expenses	Operating expenses									Operating expenses
Research and development(1)	Research and development(1)	38,898		30,873		112,889		85,610		Research and development(1)	44,481		38,161
Sales and marketing(1)	Sales and marketing(1)	63,171		43,192		184,096		128,613		Sales and marketing(1)	65,000		57,642
General and administrative(1)	General and administrative(1)	31,407		26,083		93,872		81,969		General and administrative(1)	29,287		29,141
Provision for transaction losses	Provision for transaction losses	10,137		1,377		18,918		3,701		Provision for transaction losses	6,701		2,129
Total operating expenses	Total operating expenses	143,613		101,525		409,775		299,893		Total operating expenses	145,469		127,073
Loss from operations	Loss from operations	(25,442)		(8,317)		(72,142)		(32,409)		Loss from operations	(25,038)		(23,652)
Interest expense	Interest expense	1,117		746		3,362		1,055		Interest expense	1,101		1,125
Other (income) expense, net		(1,772)		222		(2,215)		161
Loss before income taxes		(24,787)		(9,285)		(73,289)		(33,625)
Other income, net										Other income, net	(44,101)		(68)
Income (loss) before income taxes										Income (loss) before income taxes	17,962		(24,709)
Income tax provision	Income tax provision	(40)		(26)		(96)		(59)		Income tax provision	(795)		(29)
Net loss		$	(24,827)	$	(9,311)	$	(73,385)	$	(33,684)
Net income (loss)										Net income (loss)	$	17,167	$	(24,738)

2223

(1) Includes stock-based compensation expense as follows:


		Three Months Ended September 30,				Nine Months Ended September 30,					Three Months Ended March 31,
(In thousands)	(In thousands)	2022		2021		2022		2021		(In thousands)	2023		2022
Cost of revenue	Cost of revenue	$	376	$	202	$	962	$	582	Cost of revenue	$	420	$	239
Research and development	Research and development	7,337		4,036		19,517		11,321		Research and development	7,629		5,615
Sales and marketing	Sales and marketing	3,055		1,472		7,983		4,363		Sales and marketing	3,568		2,265
General and administrative	General and administrative	9,636		8,196		27,657		22,400		General and administrative	8,283		8,616
Total stock-based compensation	Total stock-based compensation	$	20,404	$	13,906	$	56,119	$	38,666	Total stock-based compensation	$	19,900	$	16,735

Comparison of the Three ~~and Nine~~ Months Ended ~~September 30,~~March 31, 2023 and 2022 ~~and 2021~~

Revenue


		Three Months Ended September 30,										Nine Months Ended September 30,											Three Months Ended March 31,
(In thousands, except percentages)	(In thousands, except percentages)	2022			2021			Change				2022			2021			Change				(In thousands, except percentages)	2023			2022			Change
Marketplace	Marketplace	$	145,143		$	117,783		$	27,360	23	%	$	418,893		$	336,913		$	81,980	24	%	Marketplace	$	148,088		$	129,425		$	18,663	14	%
Percentage of total revenue	Percentage of total revenue	91		%	92		%					92		%	92		%					Percentage of total revenue	92		%	92		%
Managed services	Managed services	13,498			10,358			3,140		30	%	37,983			29,028			8,955		31	%	Managed services	12,770			11,912			858		7	%
Percentage of total revenue	Percentage of total revenue	9		%	8		%					8		%	8		%					Percentage of total revenue	8		%	8		%
Total revenue	Total revenue	$	158,641		$	128,141		$	30,500	24	%	$	456,876		$	365,941		$	90,935	25	%	Total revenue	$	160,858		$	141,337		$	19,521	14	%

InOur first quarter results were impacted by a number of factors, including changes to client fees as a result of the ~~third quarter of~~shift to our Client Marketplace offering in April 2022 ~~we continued~~and challenging macroeconomic conditions. As a result, GSV remained flat at $1.0 billion during the three months ended March 31, 2023, as compared to ~~execute on our strategic initiatives, including investing~~the same period in ~~sales to acquire new Upwork Enterprise clients, marketing to drive brand awareness, and research and development to enhance platform functionality and infrastructure.~~2022. The number of active clients increased 9%4% as of ~~September 30, 2022~~March 31, 2023, as compared to the same period in 2021. We believe that the decline in the year-over-year growth rate of active clients since the second quarter of 2021—when it reached 27%, the highest level since our initial public offering—is in large part due to the lapping of prior periods during which we experienced an acceleration of active client growth, driven by an acceleration in the shift toward remote work, due in part to the COVID-19 pandemic. We expect the year-over-year growth rate of active clients to decrease in the fourth quarter of 2022, ~~as compared to the third quarter of 2022. Additionally,~~and our GSV per active client increased ~~13%~~5% as of ~~September 30, 2022,~~March 31, 2023, as compared to the same period in 2021, driven by increased spend from existing clients. The growth in active clients and GSV per active client contributed to the year-over-year growth of GSV and marketplace revenue. For the three and nine months ended September 30, 2022, GSV increased 14% and 20%, respectively, as compared to the same periods in 2021. In April 2022, we combined our Upwork Basic and Plus client offerings into our new Client Marketplace offering, which simplifies our pricing model for clients of those offerings. This model makes available the most popular features of the legacy Upwork Plus offering, while eliminating the monthly client subscription fees and moving to a client marketplace fee of 5% on each transaction—or 3% if paid via ACH for eligible clients. This pricing change resulted in greater revenue and a higher marketplace take rate, but also drove some reduction in client spend. Additionally, in the third quarter, we experienced seasonal and challenging macroeconomic conditions that were initially observed in the second quarter of 2022. As a result of the pricing change and the seasonal and macroeconomic conditions, GSV decreased in the third quarter, as compared to the second quarter of 2022.

For the three months ended ~~September 30, 2022, marketplace revenue represented 91% of total revenue and increased by $27.4 million, or 23%, compared to the same period in 2021. For the nine months ended September 30, 2022,~~March 31, 2023, marketplace revenue represented 92% of total revenue and increased by ~~$82.0~~$18.7 million, or ~~24%~~14%, as compared to the same period in ~~2021.~~2022. Marketplace revenue was ~~driven by client spend, which for the three and nine months ended September 30, 2022, drove increases in talent service~~

~~fees of 6% and 14%, respectively, as compared to the same periods in 2021. Marketplace revenue was also~~ driven by the changes to client fees as a result of the shift to our ~~new~~ Client Marketplace offering in April 2022, which resulted in ~~increases~~an increase in client marketplace fees ~~(previously referred to as client payment processing and administrative fees)~~ of ~~96% and 68%~~80%, ~~respectively,~~ as compared to the same ~~periods~~period in ~~2021.~~2022. Our Client Marketplace offering also drove marketplace revenue ~~grew~~to grow at a faster rate than GSV from our marketplace offerings in the ~~third~~first quarter of 2022, and for the three and nine months ended September 30, 2022, our marketplace take rate was 14.3% and 13.8%, respectively, as compared to 13.2% and 13.3%, respectively, for the same periods in 2021. This trend was primarily a result of client fee changes related to the shift to our new Client Marketplace offering, partially offset by existing clients maturing into higher value clients and continuing to increase their spend with particular talent,2023, which resulted in a higher mix of talent at the lower rates of our tiered service fee structure. As a result of the new client fee changes resulting from our new Client Marketplace offering, we expect marketplace revenue andcaused marketplace take rate to ~~continue~~increase to ~~increase in~~14.9% for the ~~fourth quarter of 2022~~three months ended March 31, 2023, as compared to 13.1% for the ~~fourth quarter of 2021.~~same period in 2022. Additionally, during the three ~~and nine~~ months ended ~~September 30, 2022,~~March 31, 2023, we continued our efforts to better address large enterprise and other clients ~~and prospects with larger, longer-term independent talent needs~~ through our Upwork Enterprise and other premium offerings. As a result, for the three ~~and nine~~ months ended ~~September 30, 2022,~~March 31, 2023, Enterprise Revenue increased ~~41%~~6% to ~~$12.5~~$11.4 million, ~~and 46% to $35.6 million, respectively,~~ as compared to the same ~~periods~~period in ~~2021,~~2022, which also drove the increase in marketplace ~~revenue in those periods.~~

For the three ~~and nine~~ months ended ~~September 30, 2022,~~March 31, 2023, managed services revenue grew ~~at a faster rate than our marketplace revenue~~by 7% to $12.8 million, as compared to the same period in 2022, as a result of increased spend from existing clients of our managed services offering.

Cost of Revenue and Gross Margin


		Three Months Ended September 30,										Nine Months Ended September 30,											Three Months Ended March 31,
(In thousands, except percentages)	(In thousands, except percentages)	2022			2021			Change				2022			2021			Change				(In thousands, except percentages)	2023			2022			Change
Cost of revenue	Cost of revenue	$	40,470		$	34,933		$	5,537	16	%	$	119,243		$	98,457		$	20,786	21	%	Cost of revenue	$	40,427		$	37,916		$	2,511	7	%
Components of cost of revenue:	Components of cost of revenue:																					Components of cost of revenue:
Cost of talent services to deliver managed services	Cost of talent services to deliver managed services	9,591			8,189			1,402		17	%	27,822			23,192			4,630		20	%	Cost of talent services to deliver managed services	9,533			8,959			574		6	%
Other components of cost of revenue	Other components of cost of revenue	30,879			26,744			4,135		15	%	91,421			75,265			16,156		21	%	Other components of cost of revenue	30,894			28,957			1,937		7	%
Total gross margin	Total gross margin	74		%	73		%					74		%	73		%					Total gross margin	75		%	73		%

For the three ~~and nine~~ months ended ~~September 30, 2022,~~March 31, 2023, cost of revenue increased primarily as a result of increases in payment processing fees of ~~$3.1~~$1.1 million, ~~and $13.0 million, respectively,~~ as compared to the same ~~periods~~period in ~~2021,~~2022. Payment processing fees increased primarily due to increased client ~~spend, as well as~~spend. The increase in cost of revenue was also driven by increases in cost of talent services to deliver managed services resulting from ~~increases in~~increased spend from existing clients of our managed services ~~revenue.~~offering.

We expect cost of revenue to increase in absolute dollars in future periods as we continue to support growth on our work marketplace. Amounts paid to talent in connection with our managed services offering are tied to the volume of managed services used by our clients. The level and timing of these items could fluctuate and affect our cost of revenue in the future. Additionally, in ~~April 2022,~~March 2023, we ~~combined~~announced (i) the retirement of our ~~Upwork Basic and Plus client offerings into~~tiered service fee structure for talent working with clients on our ~~new~~ Client Marketplace ~~offering, which resulted~~ offering—ranging from 5% to 20%—in favor of a ~~change in pricing structure.~~flat fee of 10% and (ii) a contract initiation fee up to $4.95 per contract for clients on our Client Marketplace. We expect ~~this change~~these changes to positively impact gross margin in future periods. While we expect gross profit to increase in absolute dollars in future periods, because our managed services revenue and marketplace revenue grow at different rates, gross margin, expressed as a percentage of total revenue, may vary from period to period.

Research and Development


		Three Months Ended September 30,										Nine Months Ended September 30,											Three Months Ended March 31,
(In thousands, except percentages)	(In thousands, except percentages)	2022			2021			Change				2022			2021			Change				(In thousands, except percentages)	2023			2022			Change
Research and development	Research and development	$	38,898		$	30,873		$	8,025	26	%	$	112,889		$	85,610		$	27,279	32	%	Research and development	$	44,481		$	38,161		$	6,320	17	%
Percentage of total revenue	Percentage of total revenue	25		%	24		%					25		%	23		%					Percentage of total revenue	28		%	27		%

For the three ~~and nine~~ months ended ~~September 30, 2022,~~March 31, 2023, research and development expense increased primarily due to ~~our investments in enhancing platform functionality and infrastructure. Specifically,~~ investments we made to increase the size of our research and development workforce that resulted in increases in personnel-related costs of ~~$9.8~~$10.0 million, ~~and $24.6 million, respectively,~~ as compared to the same ~~periods~~period in ~~2021. During the three and nine months ended September 30, 2022, we capitalized $1.4~~2022. This increase was partially offset by $1.8 million ~~and $0.8 million additional~~incremental internal-use software and platform development costs ~~than in~~that we capitalized during the three months ended March 31, 2023, as compared to the same ~~periods of 2021, respectively.~~period in 2022. Additionally, during the ~~nine~~three months ended ~~September 30,~~March 31, 2022, we incurred ~~approximately~~ $2.7 million of research and development expense related to our humanitarian response efforts related to the war ~~against Ukraine.~~in Ukraine and did not incur similar expenses in 2023.

We ~~believe continued investments~~intend to focus our investment in research and development ~~are important to attain~~on the quality and adoption of our ~~strategic objectives,~~current offerings and weproducts, and expect our research and development ~~expense to increase in absolute dollars in future periods, although this expense, expressed as a percentage of total revenue, may vary from period to period.~~

~~Sales and Marketing~~

Three Months Ended September 30, Nine Months Ended September 30,
(In thousands, except percentages) 2022 2021 Change 2022 2021 Change
Sales and marketing $ 63,171 $ 43,192 $ 19,979 46 % $ 184,096 $ 128,613 $ 55,483 43 %
Percentage of total revenue 40 % 34 % 40 % 35 %

For the three and nine months ended September 30, 2022, sales and marketing expense increased primarily due to increases in marketing and brand awareness campaigns of $13.0 million and $33.7 million, respectively, as compared to the same periods in 2021, as well as increases in personnel-related costs of $6.8 million and $19.4 million, respectively. Additionally, during the nine months ended September 30, 2022, software costs increased by $1.1 million, as compared to the same period in 2021.

In an effort to continue evolving our offerings, products, brand positioning, and marketing to better address large enterprise and other clients and prospects with larger, longer-term independent talent needs, during the three and nine months ended September 30, 2022, we continued our investments in marketing to acquire new clients and drive brand awareness, and we expect to continue these investments in the fourth quarter of 2022. Beginning in the fourth quarter of 2021, we increased our investment in sales by expanding our sales team. We expect to continue expanding our sales team in the fourth quarter of 2022 as we increase our efforts to acquire clients for our Upwork Enterprise offering. As a result, we expect sales and marketing expense to increase in absolute dollars in future periods, although this expense, expressed as a percentage of total revenue, may vary from period to period.

~~General~~Sales and ~~Administrative~~Marketing


		Three Months Ended September 30,										Nine Months Ended September 30,											Three Months Ended March 31,
(In thousands, except percentages)	(In thousands, except percentages)	2022			2021			Change				2022			2021			Change				(In thousands, except percentages)	2023			2022			Change
General and administrative		$	31,407		$	26,083		$	5,324	20	%	$	93,872		$	81,969		$	11,903	15	%
Sales and marketing																						Sales and marketing	$	65,000		$	57,642		$	7,358	13	%
Percentage of total revenue	Percentage of total revenue	20		%	20		%					21		%	22		%					Percentage of total revenue	40		%	41		%

For the three ~~and nine~~ months ended ~~September 30,~~March 31, 2023, sales and marketing expense increased primarily due to increases in personnel-related costs of $7.4 million, as compared to the same period in 2022. During the three months ended March 31, 2023, we continued our investments in marketing to acquire new clients and drive brand awareness, although at a slightly lower level than in the same period in 2022, as we strive to be more strategic and efficient around prioritizing investments.

In connection with the reduction of our workforce, reduced investment in brand awareness, and other cost-saving measures implemented in May 2023, we expect sales and marketing expense to temporarily increase in the second quarter of 2023 but then decrease throughout the second half of 2023, although this expense expressed as a percentage of total revenue may vary from period to period.

General and Administrative


	Three Months Ended March 31,
(In thousands, except percentages)	2023			2022			Change
General and administrative	$	29,287		$	29,141		$	146	1	%
Percentage of total revenue	18		%	21		%

For the three months ended March 31, 2023, general and administrative expense increased primarily due to increases in personnel-related costs of ~~$3.8~~$1.1 million and ~~$10.5~~other costs of $0.6 million, ~~respectively,~~ as compared to the same ~~periods~~period in ~~2021, primarily because of increased stock-based compensation expense, as well as $1.0 million and $5.5 million related to indirect taxes incurred in the three and nine months ended September 30,~~ 2022, ~~respectively. Additionally, for the nine months ended September 30, 2022, we incurred approximately~~partially offset by $1.3 million of ~~general and administrative expense related to~~expenses incurred during the same period in 2022 resulting from our humanitarian response efforts and charitable donations related to the war ~~against~~in Ukraine. ~~Additionally, as a result of~~

We expect to continue to invest in general and administrative expenses to achieve our shift to a flexible work model for our workforce in 2020, we subleased the entirety of our Santa Clara office space and incurred an impairment charge of $7.4 million during the nine months ended September 30, 2021 related to certain of our operating lease assets and associated property and equipment.strategic objectives. We may determine to either close or sublease certain of our other offices, either of which could result in ~~further~~ impairment charges being recognized in general and administrative expense.

~~We expect to continue to invest in general and administrative expenses to achieve our strategic objectives.~~

Provision for Transaction Losses


		Three Months Ended September 30,										Nine Months Ended September 30,											Three Months Ended March 31,
(In thousands, except percentages)	(In thousands, except percentages)	2022			2021			Change				2022			2021			Change				(In thousands, except percentages)	2023			2022			Change
Provision for transaction losses	Provision for transaction losses	$	10,137		$	1,377		$	8,760	636	%	$	18,918		$	3,701		$	15,217	411	%	Provision for transaction losses	$	6,701		$	2,129		$	4,572	215	%
Percentage of total revenue	Percentage of total revenue	6		%	1		%					4		%	1		%					Percentage of total revenue	4		%	2		%

For the three ~~and nine~~ months ended ~~September 30, 2022,~~March 31, 2023, provision for transaction losses increased by $4.6 million, or 215%, as compared to the same ~~periods~~period in ~~2021,~~2022, and represented ~~6% and~~ 4% of ~~total~~ revenue, ~~respectively, primarily~~as compared to 2% in the same period in 2022. Provision for transaction losses increased due to fraud protection fees paid to a third-party vendor and increased bad debt losses, instances of fraud, and ~~higher~~ chargeback losses. We continue to closely monitor this activity and ~~have put~~maintain a number of ~~additional~~ measures ~~in place~~designed to decrease transaction losses going forward, including increasing fraud detection efforts and resources as well as integrating with an industry-leading third-party fraud detection vendor. Additionally, during the three and nine months ended September 30, 2022, we reserved $2.7 million due to one Upwork Enterprise client’s failure to pay.

~~Interest Expense and Other (Income) Expense, Net~~

Three Months Ended September 30, Nine Months Ended September 30,
(In thousands, except percentages) 2022 2021 Change 2022 2021 Change
Interest expense $ 1,117 $ 746 $ 371 50 % $ 3,362 $ 1,055 $ 2,307 219 %
Other (income) expense, net (1,772) 222 (1,994) (898) % (2,215) 161 (2,376) (1,476) %

For the three and nine months ended September 30, 2022, interest expense increased as a result of the $575.0 million aggregate principal amount of 0.25% convertible senior notes due 2026 that we issued in a private offering in August 2021, which we refer to as the Notes. See “Note 7—Debt” of the notes to ourforward.

~~condensed consolidated financial statements included elsewhere in this Quarterly Report for additional information.~~ Interest Expense and Other Income, Net


	Three Months Ended March 31,
(In thousands, except percentages)	2023		2022		Change
Interest expense	$	1,101	$	1,125	$	(24)	(2)	%
Other income, net	(44,101)		(68)		(44,033)		*

*Not meaningful

For the three ~~and nine~~ months ended ~~September 30, 2022,~~March 31, 2023, other ~~(income) expense,~~income, net was driven by the gain on early extinguishment of debt of $38.9 million related to the Repurchases (as defined below) and an increase in interest income from our marketable securities ~~partially offset by net foreign currency transaction losses.~~of $5.0 million, as compared to the same period in 2022.

Liquidity and Capital Resources

Our principal sources of liquidity are our cash and cash equivalents and marketable securities, including the net proceeds from the sale of our 0.25% convertible senior notes due 2026, which we refer to as the Notes. Our cash equivalents and marketable securities primarily consist of money market funds, commercial paper, treasury bills, corporate bonds, U.S. government securities, asset-backed securities, and other types of fixed income securities. The primary objective of our investment activities is to preserve principal while maximizing income without significantly increasing risk. Since our inception, our business has consisted of the operation of an online work marketplace that connects business with independent talent from across the globe, and we do not make investments for trading or speculative purposes. As of ~~September 30, 2022~~March 31, 2023 and December 31, ~~2021,~~2022, we had ~~$156.4~~$102.0 million and ~~$187.2~~$129.4 million in cash and cash equivalents, respectively. As of ~~September 30, 2022~~March 31, 2023 and December 31, ~~2021,~~2022, we had ~~$519.4~~$407.6 million and ~~$497.6~~$557.2 million in marketable securities, respectively.

We believe our existing cash and cash equivalents, marketable securities, and cash flow from operations (in periods in which we generate cash flow from operations) will be sufficient for at least the next 12 months to meet our requirements and plans for cash, including meeting our working capital requirements and capital expenditure requirements. In the long term, our ability to support our working capital and capital expenditure requirements will depend on many factors, including our revenue growth rate, the timing and the amount of cash received from users, the expansion of sales and marketing activities, the timing and extent of spending to support research and development efforts, the cost to host our work marketplace, the introduction of new offerings and services, the continuing market adoption of our work marketplace, any acquisitions or investments that we make in complementary businesses, products, and technologies, macroeconomic conditions, and our ability to obtain equity or debt financing. Our principal commitments consist of obligations under our non-cancellable operating leases for office space and the Notes. There were no material changes to ~~these principal commitments~~our lease agreements from those disclosed in our Annual Report on Form 10-K for the year ended December 31, ~~2021.~~ 2022. In March 2023, we sold $138.2 million of available-for-sale marketable securities to enable the Repurchases. Assuming the remaining Notes are not converted into our common stock, repurchased, or redeemed prior to maturity, (i) annual interest expense relating to the Notes will be $2.7 million in each fiscal year through 2026 and (ii) principal in the amount of $361.0 million will be payable upon the maturity of the Notes on August 15, 2026. For additional information about our Notes, see the section below titled “—Convertible Senior Notes Due 2026.”

As market conditions warrant, we may, from time to time, repurchase additional outstanding Notes in the open market, in privately negotiated transactions, by tender offer, by exchange transaction, or otherwise. Such repurchases, if any, will depend on prevailing market conditions, our liquidity, and other factors, and may be commenced or suspended at any time. The amounts involved and total consideration paid may be material.

We anticipate satisfying our short-term cash requirements with our existing cash and cash equivalents and may satisfy our long-term cash requirements with cash and cash equivalents on hand or with proceeds from a future equity or debt financing. To the extent existing cash and cash equivalents, cash from

marketable securities, and cash from operations (in periods in which we generate cash flow from operations) are insufficient to fund our working capital and capital expenditure requirements, or should we require additional cash for other purposes, we will need to raise additional funds. In the future, we may attempt to raise additional capital through the sale of equity securities or through equity-linked or debt financing arrangements as we did with the offering of the Notes in the third quarter of 2021. If we raise additional funds by issuing equity or equity-linked securities, the ownership and economic interests of our existing stockholders will be diluted. If we raise additional financing by incurring additional indebtedness, we will be subject to additional debt service requirements and could also be subject to additional restrictive covenants, such as limitations on our ability to incur additional debt, and other operating restrictions that could adversely impact our ability to conduct our business. Any future indebtedness we incur may result in terms that could also be unfavorable to our equity investors. There can be no assurances that we will be able to raise additional capital on terms we deem acceptable, or at all. The inability to raise additional capital as and when required would have an adverse effect, which could be material, on our results of operations, financial condition, and ability to achieve our business objectives.

~~We also believe that our principal sources of liquidity will allow us to manage~~During the impact of the COVID-19 pandemic, as well as the impact of Russia’s invasion of Ukraine and our decision to suspend our business operations in Russia and Belarus, on our business operations for the foreseeable future, which could include reductions in revenue and delays in payments from users, as further described below in Part II, Item 1A, “Risk Factors” in this Quarterly Report, see the risk factors titled “Risk Factors—Our business experienced, and may again experience, an adverse impact from the ongoing COVID-19 pandemic, including as new variants of COVID-19 emerge. In addition, the positive impacts on our business resulting from the shift to remote work during the pandemic may not continue as the pandemic

subsides and the restrictions intended to prevent its spread are relaxed or lifted” and “Russia’s invasion of Ukraine and our decision to suspend our business operations in Russia and Belarus have affected and may continue to affect our business and results of operations.” The challenges posed by the ongoing COVID-19 pandemic and ongoing Russian war against Ukraine on our business are expected to continue to evolve. Consequently,periods presented, we ~~will continue to evaluate our financial position in light of future developments.~~

We did not have, ~~during the periods presented,~~ and we do not currently have, any commitments or obligations, including contingent obligations, arising from arrangements with unconsolidated entities or persons that have or are reasonably likely to have a material current or future effect on our financial condition, changes in financial condition, revenues or expenses, results of operations, liquidity, cash requirements or capital resources.

Escrow Funding Requirements

As a licensed internet escrow agent, we offer escrow services to users of our work marketplace and, as such, we are required to hold our users’ escrowed cash and in-transit cash in trust as an asset and record a corresponding liability for escrow funds held on behalf of talent and clients on our balance sheet. We expect the balances of our funds held in escrow, including funds held in transit, and the related liability to grow as GSV grows and may vary from period to period. Escrow regulations require us to fund the trust with our operating cash to cover shortages due to the timing of cash receipts from clients for completed hourly billings. Talent submit their billings for hourly contracts to their clients on a weekly basis every Sunday, and the aggregate amount of such billings is added to escrow funds payable to talent on the same day. As of each Sunday of each week, we have not yet collected funds for hourly billings from clients as these funds are in transit. Therefore, in order to satisfy escrow funding requirements, every Sunday we fund the shortage of cash in trust with our own operating cash and typically collect this cash shortage from clients within the next several days. As a result, we expect our total cash and cash flows from operating activities to be impacted when a quarter ends on a Sunday. As of ~~September 30, 2022~~March 31, 2023 and December 31, ~~2021,~~2022, funds held in escrow, including funds in transit, were ~~$170.0~~$179.4 million and ~~$160.8~~$161.5 million, respectively.

Convertible Senior Notes Due 2026

In August 2021, we issued the Notes pursuant to an Indenture between us and Wells Fargo Bank, National Association, as ~~trustee, which we refer to as the Indenture.~~

trustee. The Notes are senior, unsecured obligations and bear interest at a rate of 0.25% per year, payable semiannually in arrears, and are due August 15, 2026. Upon conversion, we have an option to pay or deliver, as the case may be, cash, shares of our common stock, or a combination of cash and shares of our common stock. ~~The net proceeds from the issuance~~

On each of March 21, 2023 and March 23, 2023, we entered into separate, privately negotiated repurchase agreements with a limited number of institutional holders of the Notes ~~were approximately $560.1~~to repurchase for cash an aggregate of $214.0 million ~~after deducting~~principal amount of the Notes, which we refer to as the Repurchases. We paid $170.8 million in cash to consummate the Repurchases. As a result, during the three months ended March 31, 2023, we recognized a gain on the early extinguishment of debt of $38.9 million, which is net of $3.7 million related to the pro-rata write-off of unamortized issuance ~~costs. We used approximately $49.4~~costs associated with the sale of the Notes in August 2021, and $0.6 million of other fees incurred to effect the Repurchases. The resulting gain on early extinguishment of debt is included in other income, net ~~proceeds from~~in the condensed consolidated statement of operations and comprehensive income (loss). As of March 31, 2023, $361.0 million principal amount of the Notes offering to pay the cost of the Capped Calls (as defined below). We intend to use the remainder of the net proceeds from the offering for general corporate purposes, including marketing, brand awareness and sales, and which may include working capital, capital expenditures, and investments in and acquisitions of other companies, products or technologies that we may identify in the future.remain outstanding.

Capped Calls

In connection with the issuance of the Notes, we entered into capped call transactions, which we refer to as Capped Calls. The Capped Calls are expected generally to reduce the potential dilution to our common stock upon any conversion of the Notes and/or offset any cash payments we are required to make in excess of the principal amount of converted Notes, as the case may be, with such reduction and/or offset subject to a cap based on the cap price.

The initial cap price of the Capped Calls is $92.74 per share of common stock, subject to certain customary adjustments under the terms of the Capped Calls. See “Note 7—Debt” of the notes to our condensed consolidated financial statements included elsewhere in this Quarterly Report for additional information regarding the Notes and the Capped Calls.

The Capped Calls remain in effect notwithstanding the Repurchases.

Cash Flows

The following table summarizes our cash flows for the periods presented:

Nine Months Ended
September 30,
(In thousands) 2022 2021
Net cash provided by (used in) operating activities $ (1,896) $ 23,284
Net cash used in investing activities (32,433) (26,114)
Net cash provided by financing activities 12,950 546,975
Net change in cash, cash equivalents, and restricted cash(1)
$ (21,379) $ 544,145
(1) Includes increases in funds held in escrow, including funds in transit of $9.2 million and $37.6 million during the nine months ended September 30, 2022 and 2021, respectively.


	Three Months Ended March 31,
(In thousands)	2023		2022
Net cash used in operating activities	$	(8,701)	$	(11,476)
Net cash provided by (used in) investing activities	152,136		(55,043)
Net cash provided by (used in) financing activities	(152,031)		36,054
Net change in cash, cash equivalents, and restricted cash(1)	$	(8,596)	$	(30,465)
(1) Includes increases in funds held in escrow, including funds in transit of $18.0 million and $35.6 million during the three months ended March 31, 2023 and 2022, respectively.

Operating Activities

Our largest source of cash from operating activities is revenue generated from our work marketplace. Our primary uses of cash from operating activities are for personnel-related expenditures, marketing activities, including advertising, payment processing fees, amounts paid to talent to deliver services for clients under our managed services offering, and third-party hosting costs. In addition, because we are licensed as an internet escrow agent, our total cash and cash ~~provided by (used in)~~used in operating activities may be impacted by the timing of the end of our fiscal quarter as discussed in the section titled “—Liquidity and Capital Resources—Escrow Funding Requirements.”

For the ~~nine~~three months ended ~~September 30,~~March 31, 2023, net cash used in operating activities was $8.7 million, which resulted from net income of $17.2 million, offset by adjustments of $15.1 million, driven by the gain on early extinguishment of debt of $38.9 million, and net cash outflows of $10.8 million from changes in operating assets and liabilities.

For the three months ended March 31, 2022, net cash used in operating activities was ~~$1.9~~$11.5 million, which resulted from a net loss of ~~$73.4~~$24.7 million and net cash outflows of ~~$14.6~~$9.6 million from changes in operating assets and liabilities, partially offset by non-cash charges of ~~$86.1~~$22.9 million. The change in operating assets and liabilities primarily resulted from the ~~increase~~decrease in ~~trade~~accrued expenses and ~~client receivables of $17.8 million. Due~~other current liabilities due to ~~fluctuations in revenue and the number of transactions on our work marketplace, coupled with fluctuations in~~ the timing of ~~cash receipts from clients,~~payments made during the three months ended March 31, 2022, as well as $4.3 million of expenses associated with our ~~trade and client receivables will likely continue~~humanitarian response efforts related to ~~fluctuate~~the war in ~~the future.~~Ukraine.

Investing Activities

For the ~~nine~~three months ended ~~September 30, 2021,~~March 31, 2023, net cash provided by ~~operating~~investing activities was ~~$23.3~~$152.1 million, which ~~resulted~~was primarily a result of proceeds from ~~non-cash charges~~maturities of ~~$61.1~~marketable securities of $167.4 million and proceeds from the sale of marketable securities of $143.7 million to enable the repurchase of a portion of

the Notes, partially offset by ~~a net loss~~investing $156.1 million in various marketable securities, as well as $2.7 million of ~~$33.7 million~~internal-use software and ~~net cash outflows of $4.1 million from changes in operating assets and liabilities. The change in operating assets and liabilities primarily resulted from~~platform development costs that we paid during the ~~increase in trade and client receivables.~~

~~Investing Activities~~period.

For the ~~nine~~three months ended ~~September 30,~~March 31, 2022, net cash used in investing activities was ~~$32.4~~$55.0 million, which was primarily a result of investing ~~$398.3~~$160.3 million in various marketable securities, as well as ~~$5.2~~$1.2 million of internal-use software and platform development costs that we paid during the period, partially offset by proceeds from maturities of marketable securities of ~~$371.9 million.~~

For the nine months ended September 30, 2021, net cash used in investing activities was $26.1 million, which was primarily a result of investing $108.8 million in various marketable securities, as well as $4.2 million of internal-use software and platform development costs that we paid during the period, partially offset by proceeds from maturities of marketable securities of $87.5$106.6 million.

Financing Activities

For the ~~nine~~three months ended ~~September 30,~~March 31, 2023, net cash used in financing activities was $152.0 million, which was driven by $170.8 million that we paid to consummate the Repurchases, partially offset by an increase in escrow funds payable of $18.0 million and cash received from stock option exercises of $0.8 million.

For the three months ended March 31, 2022, net cash provided by financing activities was ~~$13.0~~$36.1 million, which resulted primarily from an increase in escrow funds payable of ~~$9.2 million, proceeds received from our employee stock purchase plan of $2.5~~$35.6 million and cash received from stock option exercises of ~~$1.3 million.~~

~~For the nine months ended September 30, 2021, net cash provided by financing activities was $547.0 million, which resulted primarily from proceeds from the Notes, net of debt issuance costs, of $560.1~~

million, an increase in escrow funds payable of $37.6 million, cash received from stock option exercises of $6.6 million, and proceeds received from our employee stock purchase plan of $2.7 million, partially offset by purchases of the Capped Calls of $49.4 million and repayments of borrowings on debt of $10.8$0.5 million.

Critical Accounting Policies and Estimates

Our condensed consolidated financial statements are prepared in accordance with U.S. GAAP. The preparation of the condensed consolidated financial statements requires us to make estimates and assumptions that affect the reported amounts of assets, liabilities, revenue, expenses, and related disclosures. We evaluate our estimates and assumptions on an ongoing basis using historical experience and other factors and adjust those estimates and assumptions when facts and circumstances dictate. Actual results could materially differ from these estimates and assumptions.

An accounting policy is deemed to be critical if it requires an accounting estimate to be made based on assumptions about matters that are highly uncertain at the time the estimate is made, if different estimates reasonably could have been used, or if changes in the estimate that are reasonably possible could materially impact the financial statements.

Except as otherwise disclosed in “Note 2—Basis of Presentation and Summary of Significant Accounting Policies” of the notes to our condensed consolidated financial statements included elsewhere in this Quarterly Report and “Management’s Discussion and Analysis of Financial Condition and Results of Operations,” there have been no material changes to our critical accounting policies and estimates as compared to the critical accounting policies and estimates described in our Annual Report on Form 10-K for the year ended December 31, ~~2021,~~2022, which we refer to as our Annual Report.

Recent Accounting Pronouncements

See “Note 2—Basis of Presentation and Summary of Significant Accounting Policies” of the notes to our condensed consolidated financial statements included elsewhere in this Quarterly Report for recently issued accounting pronouncements not yet adopted as of the date of this Quarterly Report.

Item 3. Quantitative and Qualitative Disclosures about Market Risk.

We have operations both within the United States and internationally, and we are exposed to market risks in the ordinary course of our business. These risks primarily include interest rate and foreign currency exchange rates.

Interest Rate Risk

The primary objective of our investment activities is to preserve principal while maximizing income without significantly increasing risk. We do not make investments for trading or speculative purposes. Because our cash and cash equivalents have a relatively short maturity, our portfolio’s fair value is relatively insensitive to interest rate changes. Borrowings under the Notes have a fixed interest rate. As of ~~September 30, 2022~~March 31, 2023 and December 31, ~~2021,~~2022, we had $361.0 million and $575.0 million, respectively, aggregate principal amount of borrowings outstanding under the Notes. We do not believe that a

hypothetical increase or decrease in interest rates of 100 basis points would have a material impact on our operating results or financial condition.

Foreign Currency Risk

Our operating results and cash flows are subject to fluctuations due to changes in foreign currency exchange rates. In addition to the U.S. dollar, we offer clients the option to settle invoices denominated in the U.S. dollar in the following currencies: Euro, British Pound, Australian dollar, Canadian dollar, Singapore dollar, South African rand, New Zealand dollar, Polish zloty, Swiss franc, Norwegian krone, Danish krone, Swedish krona, Turkish lira, Japanese yen, and Hong Kong dollar. When clients make payments in one of these currencies, we are exposed to foreign currency risk during the period between when payment is made and when the payment amounts settle. To mitigate this risk, we have entered into forward contracts. As such, the impact of foreign currency exchange rate fluctuations to our operating results have been insignificant to date.

Item 4. Controls and Procedures.

Evaluation of Disclosure Controls and Procedures

Our management, with the participation of our Chief Executive Officer (our Principal Executive Officer) and Chief Financial Officer (our Principal Financial Officer), evaluated the effectiveness of our disclosure controls and procedures as defined in Rules 13a-15(e) and 15d-15(e) under the Securities Exchange Act of 1934, as amended, which we refer to as the Exchange Act, as of ~~September 30, 2022.~~March 31, 2023. Our disclosure controls and procedures are designed to ensure that information we are required to disclose in the reports we file or submit under the Exchange Act is accumulated and communicated to our management, including our Chief Executive Officer and Chief Financial Officer, as appropriate to allow timely decisions regarding required disclosures, and is recorded, processed, summarized, and reported within the time periods specified in the rules and forms of the ~~Securities and Exchange Commission, which we refer to as the~~ SEC. Based upon that evaluation, our Chief Executive Officer and Chief Financial Officer concluded that, as of ~~September 30, 2022,~~March 31, 2023, our disclosure controls and procedures were effective.

Changes in Internal Control over Financial Reporting

There were no changes to our internal control over financial reporting that occurred during the quarter ended ~~September 30, 2022~~March 31, 2023 that have materially affected, or are reasonably likely to materially affect, our internal control over financial reporting.


PART II—OTHER INFORMATION

Item 1. Legal Proceedings.

We are not a party to any material pending legal proceedings. From time to time, we may be subject to legal proceedings and claims arising in the ordinary course of business.

Item 1A. Risk Factors.

A description of the risks and uncertainties associated with our business is set forth below. You should carefully consider the risks and uncertainties described below, as well as the other information in this Quarterly Report, including our condensed consolidated financial statements and the related notes and “Management’s Discussion and Analysis of Financial Condition and Results of Operations.” The occurrence of any of the events or developments described below, or of additional risks and uncertainties not presently known to us or that we currently deem immaterial, could materially and adversely affect our business, results of operations, financial condition, and growth prospects. In such an event, the market price of our common stock could decline and you could lose all or part of your investment.

Summary of Risk Factors

Some of the more material risks that we face include:

•Our growth depends on our ability to attract and retain a community of talent and clients, and the failure to maintain or grow our community of users ~~could adversely impact~~and their activity on our ~~business.~~

•~~If we fail to maintain or increase activity by existing users~~platform in a cost-effective manner or at all could adversely impact our ~~revenue will grow more slowly than expected or may decline and our business will be adversely impacted.~~business.

•We have experienced growth in recent periods and expect to ~~continue to~~ invest in our growth ~~for~~in the ~~foreseeable~~ future. If we are unable to maintain similar levels of growth or manage our growth effectively, our business, revenue and profits, and financial condition could be adversely affected.

•We face payment and fraud risks that could adversely impact our business.

•We continue to evolve our business strategy, offerings and pricing model, and changes that we make can adversely affect our business and make it difficult to evaluate our future prospects.

•If we are unable to maintain our payment partner relationships on favorable terms, or at all, our business could be adversely affected.

•We have a limited operating history under our current business strategy and pricing model, and will continue to evolve our business strategy and pricing model, which makes it difficult to evaluate our business and future prospects.

•~~Changes to our offerings and pricing model have in the past adversely affected, and could in the future adversely affect, our business.~~

•~~Russia’s invasion of Ukraine and our decision to suspend our business operations in Russia and Belarus have affected and may continue to affect our business and results of operations.~~

•Our business experienced, and may again experience, an adverse impact from the ongoing COVID-19 pandemic, including as new variants of COVID-19 emerge. In addition, the positive impacts on our business resulting from the shift to remote work during the pandemic may not continue as the pandemic subsides and the restrictions intended to prevent its spread are relaxed or lifted.

•Our revenue growth and ability to achieve and sustain profitability will depend in part on being able to increase the productivity, effectiveness, and efficiency of our sales force.

•The positive impacts on our business resulting from the accelerated shift to remote work during the COVID-19 pandemic have not continued as the pandemic has subsided.

•Our revenue growth depends in part on the success of our strategic relationships with third parties and their continued performance.

•Users circumvent our work marketplace, which adversely impacts our business.

•Clients sometimes fail to pay their invoices, necessitating action by us to compel payment.

•We are subject to disputes with or between users of our work marketplace.

•Our inability to generate revenue from our marketplace offerings, which represents a substantial majority of our total revenue, would adversely affect our business operations, financial results, and growth prospects.

•~~If we fail to develop, maintain, and enhance our brand and reputation cost-effectively, our business and financial condition may be adversely affected.~~

•If the market for independent talent and the services they offer develops more slowly than we expect, our growth may slow or stall, and our operating results could be adversely affected.

•If we fail to develop, maintain, and enhance our brand and reputation cost-effectively, our business and financial condition may be adversely affected.

•If we are not able to develop and release new offerings and services, or develop and release successful enhancements, new features, and modifications to our existing offerings and services, our business could be adversely affected.

•We face intense competition and could lose market share to our competitors, including if we fail to continue to develop and enhance our existing offerings and services, which could adversely affect our business, operating results, and financial condition.

•~~Errors, defects,~~If we or ~~disruptions in~~ our ~~work marketplace, including any~~third-party partners experience a security breach, other hacking or phishing attack, ransomware or other malware attack, or other privacy or security incident, ~~could diminish demand, adversely impact our financial results, and subject~~whether intentionally or unintentionally caused by us ~~to liability.~~

•~~Because a substantial portion of the services offered~~or by ~~talent and sought by clients on~~third parties, our work marketplace ~~is information technology services, a decline in talent offering information technology services or the market~~may be perceived as not being secure, our reputation may be harmed, demand for ~~information technology service providers on~~ our work marketplace may be reduced, our operations may be disrupted, we may incur significant legal costs, fines, or liabilities, and our business could be adversely ~~affect our business.~~affected.

•Our sales efforts are ~~increasingly~~ primarily targeted at large enterprise and other clients and prospects with larger, longer-term independent talent needs, and as a result we may encounter greater pricing, implementation, and customization challenges, and we may incur additional costs, each of which could adversely impact our business and operating results.

•~~Users circumvent~~Because a substantial portion of the services sought by clients and offered by talent on our work marketplace ~~which~~is information technology services, a decline in client demand for, or talent offering, information technology services on our work marketplace could adversely ~~impacts~~affect our business.

•If internet search engines’ methodologies or other channels that we utilize to direct traffic to our website are modified to our disadvantage, or our search result page rankings decline for other reasons, our user growth could decline.

•Errors, defects, or disruptions in our work marketplace, including any security breach, other hacking or phishing attack, or other privacy or security incident, could diminish demand, adversely impact our financial results, and subject us to liability.

•We and our users may be subject to new and existing laws and regulations, both in the United States and internationally.

•The regulatory landscape regarding contractor classification is rapidly changing and changes in these laws could adversely affect demand for our services and work marketplace and adversely affect our business. In addition, there may be adverse tax, legal, and other consequences if the contractor classification or employment status of talent that use our work marketplace is challenged.

•Having an international community of users and engaging talent internationally exposes us to risks that could have an adverse effect on our business, operating results, and financial condition, and these risks could increase as we seek to expand our international footprint.

•There may be adverse tax, legal, and other consequences if the contractor classification or employment status of talent that use our work marketplace is challenged, and our business could be adversely affected by changes in laws regarding contractor classification.

•The success of our business relies on demand for talent and any change that affects demand for talent, including regulatory or tax changes, or adverse perception regarding use of talent, would adversely affect our business.

•We have a history of net losses, ~~anticipate increasing~~may increase our operating expenses in the future, and may not achieve or sustain profitability.

•Our operating results and performance metrics may fluctuate from ~~quarter~~period to ~~quarter,~~period, which makes our future results difficult to predict.

•We track certain performance metrics with internal tools and do not independently verify such metrics. Certain of our performance metrics may not accurately reflect certain details of our business, are subject to inherent challenges in measurement, and real or perceived inaccuracies in such metrics may harm our reputation and negatively affect our business.

•The stock price of our common stock has been and may continue to be volatile, and you could lose all or part of your investment.

•Our indebtedness could limit the cash flow available for our operations and expose us to risks that could adversely affect our business, financial condition, and results of operations.

•Adverse or changing economic and political conditions may negatively impact our business.

•We may be adversely affected by natural disasters and other catastrophic events ~~including the ongoing COVID-19 pandemic,~~or by man-made problems such as warfare, terrorism, or failures of technology, that could disrupt our business operations and our business continuity and disaster recovery plans may not adequately protect us from a serious disaster.

Risks Related to our Business Operations, Execution, and Growth

Our growth depends on our ability to attract and retain a community of talent and clients, and the failure to maintain or grow our community of users and their activity on our platform in a cost-effective manner or at all could adversely impact our business.

The size of our community of users, including both talent and clients, is critical to our success. Our ability to achieve significant growth in revenue in the future will depend, in large part, upon our ability to attract new users and retain existing users, including large enterprise and other clients with larger, longer-term independent talent needs, as well as talent that meet the criteria sought by such clients.

Talent have many different ways of marketing their services, securing clients, and obtaining payments from clients, including advertising to, and engaging with, prospective clients through other online or offline platforms and methods, signing up for online or offline third-party agencies and staffing firms, using payment services provided by third parties, or finding employment directly with a business. Likewise, there may be impediments to talent who would like to use our work marketplace, including geopolitical events military conflicts, sanctions regimes, the talent’s inability to access technology or internet, or other external causes, and these events in areas where certain talent resides. For example, at the beginning ofsuch as Russia’s invasion of Ukraine in ~~late~~ February 2022, ~~we experienced~~which resulted in immediate reductions in activity from users in the ~~region, but since that initial impact, we~~region.

Clients have ~~seen activity from users in Ukraine rebound~~similarly diverse options to ~~almost pre-war levels. Moreover,~~find and engage service providers, such as ~~a result of Russia’s war against Ukraine, we suspended business operations in Russia~~finding service providers through other online or offline platforms or through staffing firms and ~~Belarus, which means that users in each of those countries are prohibited from using our work marketplace for the duration of the suspension.~~agencies or other talent sourcing services, engaging service providers directly, or hiring temporary, full-time, or part-time employees directly or through an agency. Clients may decrease their use of, or cease using, our work marketplace and our revenue may be adversely impacted for many reasons, including: if we fail to attract new talent; if the quality or types of services provided by talent on our work marketplace are not satisfactory to clients; if generative artificial intelligence tools provide a suitable replacement for traditional talent ~~are not located in geographic regions in which clients are seeking to engage remote talent;~~tasks; or if talent decrease their use of, or cease using, our work marketplace or prefer to take remote employment opportunities or to use other online remote work platforms, both of which are increasingly available as a result of the shift to remote work.

~~Clients have similarly diverse options to find~~ Further, expenditures by clients may be cyclical and ~~engage service providers, such as finding service providers through other online~~may reflect overall macroeconomic conditions or offline platforms or through staffing firms and agencies, engaging service providers directly, using other talent sourcing services, or hiring temporary, full-time, or part-time employees directly or through an agency.

budgeting patterns. Beginning in the second half of 2019, we began evolving our offerings, services, brand positioning, and marketing to better address large enterprise and mid-market prospects and other clients with larger, longer-term independent talent needs. And more recently, we have prioritized our advertising, marketing, and product development efforts to reach those new and existing clients seeking to engage remote talent in light of the acceleration in the shift toward remote work, due in part to the COVID-19 pandemic. To further achieve our goals, we expect to increasingly engage in sophisticated, costly, and lengthy sales and marketing and internationalization or localization efforts that may not result in additional users that transact on our work marketplace or effectively retain our current users that transact on our work marketplace, or may not do so in a cost-effective manner. The evolution of these and other efforts, either individually or in the aggregate, may not be successful in attracting and retaining users or growing client spend from these target clients, and in the event these efforts result in the loss of or reduction in spend by other clients that is not offset by increased activity from these target clients, they may result in a temporary or long-term decelerating growth in, or declining, ~~GSV.~~GSV, which could adversely affect our business, revenue, financial condition, and operating results. In addition, ~~any~~the increase in user acquisition resulting from the shift toward remote work, due in part to the COVID-19 pandemic, ~~may slow or decline~~has not continued as the impact of the COVID-19 pandemic ~~subsides.~~has subsided. For example, growth in the number of active clients has decelerated on a year-over-year basis since the second quarter of 2021 and GSV growth on a year-over-year basis has decelerated since the second quarter of 2021. ~~Moreover, we expect to see the year-over-year growth rate of active clients to continue to decrease in the fourth quarter of 2022.~~ See “Management’s Discussion and Analysis of Financial Condition and Results of Operations—Active Clients and GSV per Active Client” above for the definition of active client.

~~We may modify our pricing model, or introduce new, modify, or consolidate existing offerings or other services~~Both clients and ~~features to attract and retain users. For example, in April 2022 we combined our Upwork~~

Basic and Plus client offerings into a new Client Marketplace offering which simplifies our pricing model for clients of those offerings. Such actions may negatively impact our ability to attract and retain users, increase user circumvention of our work marketplace, or otherwise cause a loss of users or a reduction of spend on our work marketplace.

If we fail to maintain or increase activity by existing users in a cost-effective manner or at all, our revenue will grow more slowly than expected or may decline and our business will be adversely impacted.

~~Users can generally decide to cease using our work marketplace and related services at any time. Users~~talent may stop using our work marketplace and related services if the quality of the user experience on our work marketplace, including our support capabilities or our ability to provide a secure, reliable, and trustworthy work marketplace, does not meet their expectations or keep pace with the quality of the user experience generally offered by competitive products and services. ~~For example, for the three~~Clients and nine months ended September 30, 2022, provision for transaction losses increased, as compared to the same periods in 2021, primarily due to increased instances of fraud and higher chargeback losses. Userstalent may also choose, and in the past have chosen, to cease using our work marketplace if they perceive that our pricing model, including associated fees, is not in line with the value they derive from our work

marketplace, or for other reasons, including cost-cutting measures. ~~Moreover, as discussed below~~For example, the shift to our Client Marketplace offering in April 2022 resulted in changes to client fees, and, in March 2023, we announced (i) the ~~risk factor titled “Users circumvent~~retirement of our tiered service fee structure for talent working with clients on our Client Marketplace offering in favor of a flat fee of 10% and (ii) a contract initiation fee up to $4.95 per contract for clients on our Client Marketplace offering. While these changes are designed to improve the health of our work marketplace, ~~which adversely impacts our business,” users circumvent~~there can be no assurances as to the ~~payment services~~impact these changes will have on our ~~work marketplace~~ability to acquire new users and talent receive payment directly or through another service, which is likely to happen more frequently following a change in pricing, such as the pricing change associated with the launch of our new Client Marketplace offering, or during a macroeconomic downturn or a period of geopolitical conflict or uncertainty, as users may be more cost-sensitive during such period. In addition, expenditures by clients may be cyclical and may reflect overall macroeconomic conditions or budgeting patterns.

retain existing users. Additionally, one client accounted for more than 10% of our trade and client receivables asfor each of ~~December 31, 2021, and three clients each accounted for more than 10% of our trade and client receivables as of December 31, 2020. Although for~~ the years ended December 31, ~~2021~~2022 and December 31, 2020, we did not have any clients that accounted for more than 10% of our revenue, a decrease in spend from any of our larger clients, or failure of our larger clients to pay us, could have an adverse effect on our operating results.

Any decrease in the attractiveness of our work marketplace, failure to attract and retain users, or reduced spending by clients could lead to decreased activity, diminished network effects, or a drop in GSV on our work marketplace, which could adversely affect our business, revenue, financial condition, and operating results. We expect our GSV to fluctuate between periods due to a number of factors, including the number of active clients on our work marketplace, macroeconomic conditions, seasonality in the labor market, the volume and characteristics of projects that are posted by clients on our work marketplace, such as size, duration, pricing, and the availability and qualification of talent to complete client projects, and other factors.

2021. If users, particularly significant clients, stop using, or reduce their use of, our work marketplace and related services for any reason, including the foregoing reasons, our revenue and business would be adversely affected.

We have experienced growth in recent periods and expect to ~~continue to~~ invest in our growth ~~for~~in the ~~foreseeable~~ future. If we are unable to maintain similar levels of growth or manage our growth effectively, our business, revenue and profits, and financial condition could be adversely affected.

We have experienced growth in a relatively short period of time. For example, our total revenue for the ~~nine~~three months ended ~~September 30, 2022~~March 31, 2023 was ~~$456.9~~$160.9 million, representing a period-over-period growth rate of ~~25% over~~14% compared to the same period in ~~2021. This revenue~~2022. However, there can be no assurance that we will be able to sustain our current or historical growth ~~was due~~rates or that any future investments in ~~part~~growth will be successful or cost-effective. For example, we have already begun to see the effects of declining growth rates as compared to corresponding periods in prior years that were more strongly affected by the shift ~~toward~~to remote work resulting from the COVID-19 pandemic and therefore may not be indicative of future growth. For example, future period-over-period growth rates of revenue and key performance metrics such as GSV and active clients, when compared against the quarterly and full-year results of 2021, may fail to meet the expectations of investors or securities analysts given the accelerated growth experienced during such

~~periods due to the COVID-19 pandemic and the resulting increased adoption of remote work and reduced seasonality experienced during such periods.~~work. Moreover, sustaining the same levels of growth in future periods will become more difficult during times of macroeconomic uncertainty, including a macroeconomic downturn or recession and rising interest rates and ~~inflation.~~inflation, such as the conditions that we have experienced beginning in the second half of 2022. Sustaining our growth will place significant demands on our management as well as on our administrative, operational, and financial resources. To manage our growth, we ~~must:~~must improve our operational, financial, and management information systems and ~~processes;~~ expand, motivate, ~~retain,~~ and effectively manage and train our ~~workforce; and effectively collaborate with our third-party partners,~~workforce, all of which can be more difficult ~~with an increasingly remote workforce and~~in a ~~highly~~ competitive labor market. If we are unable to manage our growth successfully without compromising the quality of our offerings or user experience, or if new systems that we implement to assist in managing our growth do not produce the expected benefits, our business, operating results, financial condition, and ability to successfully market our work marketplace and serve our users could be adversely affected.

Our recent and historical growth should not be considered indicative of our future performance. We have encountered, and will encounter in the future, risks, challenges, and uncertainties, including those frequently experienced by growing companies in rapidly changing and highly competitive industries and challenging macroeconomic conditions. If our assumptions regarding these risks, challenges, and uncertainties, which we use to plan and operate our business, are incorrect or change, or if we do not address these risks successfully, our financial condition and operating results could differ materially from our expectations and those of investors and securities analysts, our growth rates may slow, and our business would be adversely impacted.

We face payment and fraud risks that could adversely impact our business.

Our work marketplace systems and controls relating to customer identity verification, user authentication, and fraud detection are complex. If such systems and controls are not effective, our work marketplace may be perceived as not being secure, our reputation may be harmed, we may face regulatory action or action by our payment partners, payment networks, or other third parties, and our business may be adversely impacted. In addition, bad actors around the world use increasingly sophisticated methods, including the use of artificial intelligence, to engage in illegal activities involving the theft and misuse of personal information, such as: unauthorized or fraudulent use of another’s identity, payment information, or other information; misrepresentation of the user’s identity, location, or skills, including using accounts that they have purchased, borrowed, or leased; and the improper acquisition or use of credit or debit card details and banking or other payment account information. Further, our customers provide us with

payment card billing information online, and we do not review the physical payment cards used in these transactions, which increases our risk of exposure to fraudulent activity. These types of illegal activities have increased recently on our and similar platforms and may continue to increase as platforms like ours gain more prominence, including due to the ongoing shift toward remote work or in the event of a macroeconomic downturn. Additionally, as we become more visible as a result of our brand promotion efforts, bad

Bad actors increasingly seek to take advantage of us or our users and discover ways to evade our trust and safety efforts. For example, for the three and nine months ended September 30, 2022, provision for transaction losses increased, as compared to the same periods in 2021, primarily due to increased instances of fraud and higher chargeback losses. This conduct on our website could result in any of the following, each of which could adversely impact our business:

•~~bad actors~~also may use our work marketplace, including our payment processing and disbursement methods, to engage in unlawful or fraudulent conduct, such as money laundering, moving funds to regions or persons restricted by sanctions or export controls, terrorist financing, fraudulent sale of services, bribery, breaches of security, ~~identify theft and other~~ unauthorized acquisition of data, extortion or use of ransomware, distribution or creation of malware or viruses, piracy or misuse of software and other copyrighted or trademarked content, and other ~~misconduct;~~misconduct. These types of illegal activities have increased recently on our platform and may continue to increase. For example, for the three months ended March 31, 2023, provision for transaction losses increased, as compared to the same period in 2022, due to fraud protection fees paid to a third-party vendor and increased bad debt losses, instances of fraud, and chargeback losses. This conduct on our website could result in any of the following, each of which could adversely impact our business:

•we may be, and historically have been, held liable for the unauthorized use of credit or debit card details and banking or other payment account information and required by card issuers, card networks, banks, and other payment partners to return the funds at issue and pay a chargeback, return, or other fee, and if our chargeback or return rate becomes excessive, card networks may

also require us to pay fines or other fees, engage in remediation efforts, which can be costly and divert the attention of management, or cease doing business with us;

•the California Department of Financial Protection and Innovation, which we refer to as the DFPI, or other regulators may require us to hold larger cash reserves or take other action with respect to our internet escrow license or other licenses or licensing regimes;

•users that are subjected or exposed to the unlawful, fraudulent, or improper conduct of other users or other third parties may seek to hold us responsible for the conduct of or content posted by users, may lose confidence in and decrease use of our work marketplace, seek to obtain damages and costs, or publicize their negative experiences;

•law enforcement or administrative agencies could seek to hold us responsible for the conduct of or content posted by users, including through the use of generative artificial intelligence tools, and impose fines and penalties, bring criminal action, or require us to change our business practices, and private actions or public enforcement may increase depending on interpretations of and possible changes to intermediary liability provisions such as Section 230 of the Communications Decency Act of 1996;

•we may be subject to additional risk and liability exposure, including for negligence, fraud, or other claims, if employees or third-party service providers, including talent that provide services to us, misappropriate our banking, payment, or other information or user information for their own gain or to facilitate the fraudulent use of such information;

•we may be subject to additional risk if clients fail to pay talent for services rendered, as talent may seek to hold us responsible for the clients’ conduct and may lose confidence in and decrease or cease use of our work marketplace, may publicize their negative experiences, or seek to obtain damages and costs;

•we may be subject to additional risk if Upwork Enterprise clients fail to pay us for amounts we advance to talent on their behalf, including financial losses resulting from our inability to recover such funds;

•if talent misstate their qualifications or location, provide misinformation about their skills, identity, or otherwise, perform services they are not qualified or authorized to provide, produce insufficient or defective work product or work product with a viral or other harmful effect, clients or other third parties may seek to hold us responsible for the talents’ acts or omissions and may lose confidence in and decrease or cease use of our work marketplace, or seek to obtain damages and costs; and

•we may suffer reputational damage adversely impacting our business as a result of the occurrence of any of the above.

We do not have control over users of our work marketplace and cannot ensure that any measures we have taken to detect, prevent, and mitigate these risks will stop or minimize the use of our work marketplace for, or to further, illegal or improper purposes. We have received in the past, and are likely to continue to receive in the future, complaints, notices, and inquiries from clients, talent, and other third parties, including law enforcement, administrative agencies, payment partners, payment networks, and the press, concerning misuse of our work marketplace and wrongful conduct of other users. We have also brought claims against clients and other third parties for their misuse of our work marketplace, and may be required to bring similar claims in the future. Even if these claims do not result in litigation or are resolved in our favor, these claims, and the time and resources necessary to resolve them, could divert the attention and resources of our management, negatively impact our reputation, and adversely affect our business and operating results. In addition, while we ~~are implementing~~have implemented additional steps designed to decrease transaction losses, there is no assurance that these steps will be effective or cost efficient. Further, while we take steps to implement and improve our trust and safety program through the use of algorithms and machine learning techniques, any unauthorized or inadvertent disclosure of these tools might make our efforts to prevent fraud or the improper use of our platform temporarily less effective, and any new laws restricting our use of these techniques, or that force us to make the inner workings of these tools transparent to the public, may increase the risk of harm to our users.

We continue to evolve our business strategy, offerings and pricing model, and changes that we make can adversely affect our business and make it difficult to evaluate our future prospects.

We have over time evolved, and will continue to evolve, our sales, marketing, and brand positioning efforts, as well as our business strategy and pricing model. In the second quarter of 2021, we undertook a rebranding effort and expanded our focus on large enterprise and other clients and prospects with larger, longer-term independent talent needs. We continue to evaluate and revise our current offerings and pricing model and create and test additional offerings, pricing models, features, and services to serve these and other market segments, such as our April 2022 combination of our Upwork Basic and Upwork Plus client offerings into our Client Marketplace offering, which simplifies the pricing model for clients of those offerings.

Changes in our offerings and pricing model, and the continued evolution of our business strategy and brand positioning, subject us to a number of uncertainties, including our ability to plan for and model future growth and make accurate projections regarding our future performance. In addition, we have in the past seen, and may in the future see, unexpected or unintended negative effects as a result of changes to our pricing model, offerings, and sales, brand positioning, and marketing efforts, including increased user dissatisfaction, harm to our reputation, increased circumvention rates, reductions in the rate or size of projects that get posted or completed, a failure to attract and retain quality talent or attract new clients that spend on our work marketplace or the loss of spend from existing clients. These adverse effects may negatively affect GSV, revenue, our results of operations, and financial condition, including resulting in negative period-over-period financial results for a number of periods following the change being made. For example, changes to client fees as a result of the shift to our Client Marketplace offering in April 2022 impacted our results in the first quarter of 2023. And, in March 2023, we announced (i) the retirement of our tiered service fee structure for talent working with clients on our Client Marketplace offering in favor of a flat fee of 10% and (ii) a contract initiation fee up to $4.95 per contract for clients on our Client Marketplace offering. While these changes are designed to improve the health of our work marketplace, there can be no assurances as to the impact these changes will have on our business, operating results, and financial condition.

In addition, creating new offerings is expensive and time consuming, diverts the attention of our management, and not all offerings achieve market acceptance at the levels we expect and therefore may not be cost-effective to maintain. Moreover, if an offering does not achieve sufficient market acceptance or otherwise does not achieve its intended effect, we may expend additional resources and divert the attention of management to implement modifications in an effort to improve the offering, and these efforts

may not be successful. For example, in 2019, we launched our Upwork Business offering, focused on mid-market businesses. In the fourth quarter of 2020, we decided that it was no longer cost-effective for our sales team to sell our Upwork Business offering, which resulted in an elimination of that offering and a reduction in force of approximately one-third of our sales employees at that time.

If we are unable to maintain our payment partner relationships on favorable terms, or at all, our business could be adversely affected.

Our payment partners consist of payment processors and disbursement partners. We rely on banks and payment partners to provide us with corporate banking services, escrow trust accounts or other regulated accounts, and clearing, processing, and settlement functions for the funding of all transactions on our work marketplace and disbursement of funds to users, and we do not always have a sufficient surplus of vendors in the event one or more relationships is terminated for any reason.

Our payment partners are critical to our business. In order to maintain these relationships, we have in the past been, and may in the future be, forced to agree to terms that are unfavorable to us. If we are unable to maintain our agreements with current payment partners on favorable terms, or at all, or we are unable to enter into new agreements with new payment partners on favorable terms, or at all, our ability to collect payments and disburse funds and our revenue and business may be adversely affected. This could occur for a number of reasons, including the following with respect to our payment partners:

•our partners may be unable or unwilling or may fail to perform the services we require of them, such as processing payments to talent in a timely manner ~~including~~and in ~~a manner that is satisfactory to us as it relates to~~ compliance with ~~our contractual rights and obligations and U.S. federal, state, and international laws and regulatory~~applicable legal requirements, including sanctions ~~which may apply to our partners but not to us;~~regimes;

•a failure by us to comply with our ~~partners~~partners’ compliance standards, which could ~~and,~~result in ~~some cases, have notified us in the past that they may, increase the~~increased rates that they charge us or our users, ~~charge us~~ additional ~~amounts, reduce the~~fees or a reduction in services or benefits that they provide to us with, or ~~require~~termination of our agreement with them altogether, and any remediation efforts undertaken by us to ~~undertake remediation efforts with respect~~return to ~~certain of their~~ compliance ~~standards, or we may voluntarily undertake such remediation efforts, which~~ may be costly, time consuming, and divert the attention of ~~management, especially in light of changes in those partners’ interpretation and enforcement of their rules, increased declines of client payment methods, or increased client-issued chargebacks;~~

•we may choose to cease doing business with our partners for a number of reasons, including as a result of their failure to comply with applicable payment or banking regulations or contractual requirements or due to allegations of fraud or other impropriety by them or their third-party partners;management;

•our partners may be subject to investigation, regulatory enforcement, or other proceedings that result in their inability or unwillingness to provide services to us or our unwillingness to continue to partner with them;

•our partners may be unable to effectively accommodate changing service needs, such as those that could result from rapid growth or higher volume or those which relate to international expansion and local jurisdictions, and we may have difficulty finding suitable partners to accommodate such needs;

•our partners could choose to terminate or not renew their agreements with us, or only be willing to renew or enter into agreements on different or less advantageous terms, which among other things, could negatively impact the revenue we derive from such agreements;

•our partners could reduce the services provided to us, cease doing business with us, cease or become prohibited from doing business with certain of our users or in jurisdictions where we have users, including ~~recent~~ decisions of some payment partners to cease offering services in Russia or Belarus, or cease doing business altogether; or

•our partners could be subject to delays, limitations, or closures of their own businesses, networks, partners, or systems, causing them to be unable to process payments or disburse funds for certain periods of ~~time; or~~time.

•In addition, we may be forced to cease doing business with certain partners if card network operating rules, certification requirements and laws, regulations, or rules governing electronic funds transfers to which we are subject, change or are interpreted to make it difficult or impossible for us to comply.

We have a limited operating history under our current business strategy and pricing model, and will continue to evolve our business strategy and pricing model, which makes it difficult to evaluate our business and future prospects.

We recently evolved, and will continue to evolve, our sales, marketing, and brand positioning efforts, as well as our business strategy and pricing model. Recently, we have undertaken a rebranding effort and expanded our focus on large enterprise and other clients and prospects with larger, longer-term independent talent needs. In an effort to better serve this market segment, we recently expanded our Upwork Enterprise offering, which is designed to help large enterprise businesses connect with talent and provide clients with additional offerings and services. We continue to evaluate and revise our current offerings and pricing model and create and test additional offerings, pricing models, features, and services to serve these and other market segments, such as our recent combination of our Upwork Basic and Plus client offerings into our new Client Marketplace offering, which simplifies the pricing model for clients of those offerings. We regularly launch new offerings such as “Project Catalog,” a feature through which talent can market pre-scoped projects that are easily purchased via a click-and-buy experience. Creating new offerings is expensive and time consuming, diverts the attention of our management, and not all offerings achieve market acceptance at the levels we expect and therefore may not be cost-effective to maintain. For example, in 2019, we launched our Upwork Business offering, focused on mid-market businesses. In the fourth quarter of 2020, we decided that it was no longer cost-effective for our sales team to sell our Upwork Business offering. This decision resulted in a reduction in force of approximately one-third of our sales employees in the fourth quarter of 2020. Moreover, if an offering does not achieve sufficient market acceptance or otherwise does not achieve its intended effect, we may expend additional resources and divert the attention of management to implement modifications in an effort to improve the offering, and these efforts may not be successful.

Changes in our offerings and pricing, and the continued evolution of our business strategy, subject us to a number of uncertainties, including our ability to plan for and model future growth and make accurate projections regarding our future performance. In addition, we have in the past seen, and may in the future see, unexpected or unintended negative effects, as a result of changes to our pricing model, offerings, and sales, brand positioning, and marketing efforts, including a failure to attract and retain quality talent or attract new clients that spend on our work marketplace or the loss of spend from existing clients. We cannot ensure that we will be successful in addressing these and other challenges we may face in the future, and our business may be adversely affected if we do not manage these challenges successfully.

~~Changes to our offerings and pricing model have in the past adversely affected, and could in the future adversely affect, our business.~~

From time to time we have made, and will continue to make, changes to our offerings and pricing model, and such changes may negatively impact GSV, spend on our work marketplace, circumvention rates, and other aspects of our business. Changes to any components of our pricing model have in the past, and may in the future, among other things, result in user dissatisfaction, increased circumvention, lead to a loss of GSV, revenue, or users, result in a change to the way we recognize revenue, reduce the amount of revenue we generate as a percentage of GSV, affect the taxability of our services and increase our tax exposure, reduce the rate or size of projects that get posted or completed on our work marketplace, negatively impact fill rates for projects on our work marketplace, or otherwise negatively impact our reputation, operating results, financial condition, and cash flows. For example, we experienced a quarter-over-quarter decline in GSV in the third quarter of 2022 that was attributable primarily to our consolidation of our Upwork Basic and Plus offerings into our new Client Marketplace Offering and the associated pricing change.

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~~Russia’s invasion of Ukraine and our decision to suspend our business operations in Russia and Belarus have affected and may continue to affect our business and results of operations.~~

In February 2022, Russian military forces invaded Ukraine, and war and disruption in the region is ongoing and likely to continue. Historically, we have had a business presence in Russia, Ukraine, and Belarus. At the beginning of the invasion in late February 2022, we experienced immediate reductions in activity from talent in the region, but since that initial impact, we have seen activity from users in Ukraine rebound to almost pre-war levels. Approximately 10% of our total revenue in 2021 was derived from work where either the talent or the client was located in the region. Nearly all such revenue was derived from work performed by talent inside the region for clients located in other parts of the world. Moreover, approximately 25% of client spend from our web, mobile, and software development category in 2021 was derived from work where either the talent or the client was located in the region.

In March 2022, we suspended business operations in Russia and Belarus, announcing that contracts with talent or clients in Russia or Belarus would be required to wind down by May 1, 2022. Users in Russia and Belarus are no longer able to sign up for new accounts, initiate contracts, or be visible in search on our work marketplace. Our decision to suspend operations in Russia and Belarus, as well as any disruptions to our business in Ukraine, has and will likely continue to negatively impact our financial performance and condition, including GSV and revenue. For example, during the three months ended June 30, 2022, we estimate that the loss of revenue resulting from Russia’s invasion of Ukraine and our resulting suspension of business operations in Russia and Belarus was approximately $4 million. See “Management’s Discussion and Analysis of Financial Condition and Results of Operations—Revenue” above for additional information.

As of December 31, 2021, approximately 10% of our team members were located in Ukraine, Russia, or Belarus, including nearly one-third of our engineering team. We have undertaken extensive efforts to support our team members in the region, including financial and other forms of support and paying certain expenses for those team members seeking to relocate from the affected region. In connection with our efforts, we have experienced and may continue to experience increased costs as we relocate team members and their families, and as we shift our resources to other geographies, especially if we are unable to achieve the same level of cost efficiencies. Our relocation efforts may take longer than expected and may not be successful, particularly if there is not sufficient talent available on our work marketplace to perform the work previously performed by the impacted talent or the impacted talent is unable or unwilling to remain relocated.

~~The potential impacts of Russia’s invasion of Ukraine include, but are not limited to:~~

•reduced demand on our work marketplace, resulting in lower GSV and revenue growth, including as a result of clients needing to curtail business expenses and as a result of decreased availability of talent, particularly in the web, mobile, and software development category;

•~~reduced GSV and revenue as a result of increased user circumvention of our work marketplace;~~

•increased risk of data breach and other threats from ransomware, destructive malware, distributed denial-of-service attacks, as well as fraud, spam, and fake accounts, cyber-attacks, or other illegal activity conducted either as a result of our decision to suspend operations in Russia and Belarus or more generally by bad actors seeking to take advantage of us, our users, or our third-party partners;

•reduced availability of our team members in the region, particularly our engineering team members who have not relocated, who are only willing or able to relocate temporarily, who are unable or unwilling to continue working for us, or who are not expected to relocate, out of Russia, Belarus, or Ukraine;

•difficulty in business planning and forecasting in the short term due to significant uncertainty in the impact of the war on all aspects of our business and on our clients, talent, and other business partners;

•~~increased costs and the diversion of management’s attention related to oversight of our international operations;~~

•~~delays in enhancements to our technology and features on our work marketplace as a result of the decreased availability and size of our engineering team;~~

•impacts on or decisions taken by payment partners or other critical third-party partners that may cause delays in processing payments or disrupt our ability to process payments by clients or to talent or other important functions of our work marketplace, result in an increase in payment transaction costs, lead to loss of revenue, or cause a decline in quality or availability of services, negatively affect our reputation or user activity on our work marketplace, or increase our operating costs;

•~~reputational harm to our business in Russia and Belarus or elsewhere as a result of our decision to suspend operations in those countries, as well as the potential emergence of local competition;~~

•~~retaliatory actions by Russia or other countries against us and other Western companies that chose to limit or remove business operations in the region;~~

•~~any devaluation of local currency or other inflationary effects caused by the impact of sanctions and other macroeconomic effects of the war;~~

•hesitancy among clients to engage with talent in the region and surrounding countries even after the conclusion of the conflict due to various factors, including unpredictability of laws and restrictions due to the presence of authoritarian governments in the region, as well as related security and business continuity concerns;

•~~disruption to our operations in the region due to the decisions of other companies that form part of our business ecosystem to withdraw from, or end their services in, the region;~~

•~~significant volatility and disruption of global financial markets, which may impact our GSV as a result of client behavior in the region and surrounding areas; and~~

•~~de-globalization, which among other things, may result in clients being less willing to connect with non-U.S. talent on our work marketplace~~.

In addition, sanctions and trade control measures implemented against Russia in response to the war may have an impact on our ability to operate in the ordinary course of business. For example, the significant expansion of the sanctions imposed by the European Union, which we refer to as the EU, the United Kingdom, the United States, Canada, and other jurisdictions and targeting of major financial institutions, in addition to other measures to limit Russia's access to global financial markets and systems—particularly the removal of certain banks from the SWIFT messaging system—and resulting steps by financial institutions to de-risk more broadly, may have a material impact on our ability to make payments to and receive payments from individuals or entities in the region. These and future measures may also have an impact on our ability to continue supporting business in Ukraine or elsewhere in the region, including any sanctioned regions, such as the so-called Donetsk People’s Republic and Luhansk People’s Republic. Any Russian use of unconventional weapons would likely result in the United States and EU imposing blocking sanctions targeting Russia and the enforcement of secondary sanctions against banks in China, India, or other markets that have continued to transact with Russian entities, and this may disrupt our ability to transact with entities located in those countries.

These measures and others which may be implemented by the authorities in certain of these jurisdictions are complex and still evolving. Our efforts to comply with such measures may be costly, time consuming, and divert the attention of management. Any alleged or actual failure to comply with these measures in connection with the suspension of our business operations in Russia and Belarus may subject us to government scrutiny, civil or criminal proceedings, sanctions, and other liabilities, which may have a material adverse effect on our international operations, financial condition, and results of operations.

~~In light of all of these events, we have further developed and are continuing to refine our business continuity plan and crisis response materials designed to mitigate the impact of disruptions to our~~

business, but it is unclear if our plan will successfully mitigate all disruptions. If our business continuity plan fails to mitigate some or all disruptions, it could have a material adverse impact on our business, financial condition, and results of operations.

Any of the abovementioned factors could affect our business, prospects, financial condition, and results of operations. The extent and duration of the military action, sanctions, and resulting market disruptions are impossible to predict, but could be substantial. Any such disruptions may also magnify the impact of other risks described in this Quarterly Report.

Our business experienced, and may again experience, an adverse impact from the ongoing COVID-19 pandemic, including as new variants of COVID-19 emerge. In addition, the positive impacts on our business resulting from the shift to remote work during the pandemic may not continue as the pandemic subsides and the restrictions intended to prevent its spread are relaxed or lifted.

The COVID-19 pandemic adversely impacted our business for a period of time and resulted in reductions in demand for our offerings and services by some of our clients, including small- and medium-sized business clients, which were impacted the most by the resulting macroeconomic downturn and from which we derive a substantial portion of our GSV and revenue. Conversely, beginning in 2020 we experienced an increase in GSV and revenue growth driven by an acceleration in the shift toward remote work, due in part to the COVID-19 pandemic. We do not expect these positive impacts to continue as the pandemic subsides and the restrictions intended to prevent its spread are relaxed or lifted, which may negatively impact our GSV and revenue growth.

The extent to which the ongoing COVID-19 pandemic will adversely affect our business, financial condition, results of operations, and cash flow will depend on future developments, which are highly uncertain and cannot reasonably be predicted with confidence at this time, including: the duration, spread, and severity of the outbreak, or the occurrence of additional “waves” of the outbreak; the emergence of variant strains of the virus; the availability, utilization, and efficacy rates of vaccinations; government responses to the pandemic and potential restrictions on our business and the businesses of our users; the impact of the pandemic on the U.S. and global economies and demand for our offerings; how quickly and to what extent normal economic and operating conditions resume; and the reaction of users and potential users to these developments, among others. The potential impacts of such developments include, but are not limited to:

•decline or reduction in demand on our work marketplace, resulting in lower GSV and revenue growth, during and following relaxation or lifting of restrictions intended to prevent the spread of COVID-19;

•~~diminished ability to acquire new clients, particularly large enterprise and other clients with larger, longer-term independent talent needs;~~

•~~reduced client spend on our offerings and services;~~

•~~increased competition as new competitors enter our market segment due to the accelerated shift toward remote work;~~

•~~increased costs as a result of marketing, sales, and promotional efforts;~~

•~~increased risk of data breach or cybersecurity incidents as a result of additional workers accessing corporate systems remotely;~~

•~~increased risk of fraud, cybersecurity attacks, or other illegal activity conducted by bad actors seeking to take advantage of our users or us due to the uncertainty around the COVID-19 pandemic;~~

•increased employee and contractor attrition and reduced availability of key personnel to conduct important business activities, such as providing support to users and developing new offerings or services;

•~~reduced ability to retain, attract, train, and integrate highly skilled personnel;~~

•any impairment charges on our operating lease asset and related leasehold improvements being recognized as a general and administrative expense due to a reduction to our office space and our potential sublease of such office space at a rental rate that is less than our rent expense for such office space, or any termination fees we may incur as a result of our termination of the operating lease for such office space. For example, as a result of our shift to a flexible work model for our workforce, in 2021 we subleased the entirety of our former headquarters in Santa Clara, California and a portion of our current headquarters in San Francisco, California, and, as a result, we incurred impairment charges of $8.7 million;

•~~reduced spend by clients or availability of talent located in areas or regions more affected by the COVID-19 pandemic;~~

•~~reduced GSV and revenue as a result of increased user circumvention of our work marketplace;~~

•~~reduced GSV and revenue as a result of talent reducing the fees they charge to clients due to an excess number of talent joining our work marketplace;~~

•difficulty in business planning and forecasting due to significant uncertainty in the impact of the COVID-19 pandemic on all aspects of our business and on our clients, talent, and other business partners;

•~~longer sales cycles due to slower decision-making, reduced budgets, or delays in planned work by existing and potential clients;~~

•impacts on payment partners, disbursement partners, or other critical third-party partners that may cause delays in processing payments to talent or other important functions of our work marketplace, result in an increase in payment transaction costs, lead to loss of revenue, or cause a decline in quality or availability of services, negatively affect our reputation or user activity on our work marketplace, or increase our operating costs;

•delayed or missed client payments to us or talent, which may also result in reductions in revenue, increased transaction losses, numbers of disputes with users, and costs as we seek to compel payment, which we may not be able to recover;

•~~significant disruption of global financial markets, which may impact our ability to access capital now or in the future or make capital available only on terms less favorable to us;~~

•~~reduced sublease income as a result of our sublease tenants being unable or unwilling to make the rental payments set forth in their respective sublease agreement;~~

•~~impairments to our goodwill or other long-term assets if their carrying value exceeds their fair value;~~

•increased obligations to satisfy our escrow funding requirements with our own funds or by drawing on our line of credit as a result of more frequent declines of client payment methods or increased client-issued chargebacks, which would negatively impact our cash flows and may result in higher credit card processing fees; and

•~~de-globalization, which may result in clients being less willing to connect with non-U.S. users of our work marketplace.~~

Although the COVID-19 pandemic did not have a material adverse impact on our financial results for the year ended December 31, 2021 or the nine months ended September 30, 2022, the rapidly changing market and macroeconomic conditions caused by the COVID-19 pandemic impacted the business of many of our clients, which resulted in a reduction in spend on our work marketplace for some of those affected clients. There can be no assurance that the positive impacts from the COVID-19 pandemic, such as increased talent and client acquisitions, increased client spend, and increased client retention, will continue to offset those parts of our business that have been adversely impacted. Many of these risk factors are unpredictable and outside of our control, and any of these factors could amplify the other risks

and uncertainties described elsewhere in this Quarterly Report. It is uncertain what impact that the various legislative and other government responses being undertaken in the United States and other countries, including with respect to the approval and distribution of vaccines, in which our users are located will have on the economy, our industry, our partners, our users, and our company. In connection with the COVID-19 pandemic, we have also implemented measures to protect the health of our workforce, including by adopting a flexible work model for our workforce that we believe will result in most of our employees working remotely even after the pandemic is over. These measures may negatively impact the health and safety of our employees, impact workforce productivity, increase the risk of data security breaches and other privacy and security incidents, and may cause other disruptions to our business. As offices reopen, our efforts to comply with applicable health guidelines may not prove sufficient to protect the health of our employees and other visitors to our offices, and our adoption of these measures may adversely affect our business operations. Even after the COVID-19 pandemic has subsided, we may continue to experience adverse impacts to our business. In particular, any increase in client acquisition due to the shift toward remote work as a result of the COVID-19 pandemic may slow or decline as the impact of the COVID-19 pandemic subsides and businesses shift back to in person work. For example, growth in the number of active clients has decelerated on a year-over-year basis since the second quarter of 2021 and GSV growth on a year-over-year basis has decelerated since the second quarter of 2021. Moreover, we expect to see the year-over-year growth rate of active clients to continue to decrease in the fourth quarter of 2022. See “Management’s Discussion and Analysis of Financial Condition and Results of Operations—Active Clients and GSV per Active Client” above for the definition of active client.

Our revenue growth and ability to achieve and sustain profitability will depend in part on being able to increase the productivity, effectiveness, and efficiency of our sales force.

In order to increase our revenue from our premium offerings and achieve and sustain profitability, we must improve the effectiveness and efficiency of our sales force and generate additional revenue from new and existing users. For example, in the fourth quarter of 2020, we completed an evaluation of the efficiency, productivity, and effectiveness of our sales force at generating revenue from our Upwork Business offering, as well as our other premium offerings. As part of this evaluation, we undertook a reduction in force of approximately one-third of our sales employees in an effort to drive efficiencies in our sales organization. Moreover, in the fourth quarter of 2021, we began increasing our investment in sales by expanding our sales team and we expect this investment to continue through the remainder of 2022 as we increase our efforts to acquire large enterprise and other clients for our Upwork Enterprise and other premium offerings.

~~There is significant competition for sales personnel with the skills and technical knowledge required to maintain a productive and efficient sales force.~~ Our ability to achieve significant revenue growth will depend, in large part, on our success in recruiting, training, effectively deploying, and retaining sufficient numbers of sales and sales support personnel to support our growth. It is difficult at times to find and ~~we may be unable to~~ retain a sufficient number of sales personnel with the specific skills and technical knowledge needed to effectively sell our Upwork Enterprise and other premium offerings, particularly in ~~light~~times of ~~the current global labor shortage.~~significant competition for qualified personnel. Furthermore, hiring and effectively deploying sales personnel ~~particularly in new markets,~~ is complex and requires additional costs that we may not recover if the sales personnel fail to achieve full productivity. Even if we are able to hire qualified sales personnel, doing so may be costly and lengthy, as new sales personnel require significant training and can take a number of months to achieve full productivity. In addition, new sales personnel do not always achieve productivity milestones within the timelines that we have projected, or at all, negatively impacting our ability to achieve our long-term financial projections associated with such personnel. The COVID-19 pandemic and restrictions intended to prevent its spread adversely affected the productivity of our sales force for a period of time. Moreover, our sales personnel may become less productive during a macroeconomic downturn, or otherwise during times of macroeconomic uncertainty, due to prospective clients’ having reduced budgets. If our sales personnel are not successful in obtaining new business or increasing sales to our existing user base, our business and results of operations will be adversely affected. For example, in the fourth quarter of 2021, we began increasing our investment in sales by expanding our sales team, which continued throughout 2022. However, in light of macroeconomic conditions as well as our efforts to reduce spend and streamline operations, we implemented a reduction of our workforce in May 2023, largely in our sales team. In addition, in May 2023, we announced that Eric Gilpin, our Chief Sales Officer, will depart from Upwork in the second quarter of 2023. There can be no assurance that these actions will increase the productivity or efficiency of our sales force.

The positive impacts on our business resulting from the accelerated shift to remote work during the COVID-19 pandemic have not continued as the pandemic has subsided.

Beginning in 2020 we experienced an increase in GSV and revenue growth driven by an acceleration in the shift toward remote work, due in part to the COVID-19 pandemic. These positive impacts have not continued as the pandemic has subsided. For example, growth in the number of active clients has decelerated on a year-over-year basis since the second quarter of 2021 and GSV growth on a year-over-year basis has decelerated since the second quarter of 2021. See “Management’s Discussion and Analysis of Financial Condition and Results of Operations—Active Clients and GSV per Active Client” below for the definition of active client. The extent to which the prevalence of remote work will wane as a result of the COVID-19 pandemic subsiding is uncertain and cannot reasonably be predicted at this time.

Our revenue growth depends in part on the success of our strategic relationships with third parties and their continued performance.

To grow our business, we need to continue to establish and maintain relationships with third parties, such as staffing providers, banks, software and technology vendors, and payment processing and disbursement providers. For example, we work with third-party staffing providers, upon which we are dependent to support our employment offering, Upwork Payroll. As our agreements with third-party partners terminate or expire, we may be unable to renew or replace these agreements on favorable terms, or at all. Moreover, we cannot guarantee that the parties with which we have strategic relationships will continue to offer the services for which we rely on them at economically reasonable terms or at all, devote the resources necessary to expand our reach, increase our distribution, or support an increased number of users and associated use cases. ~~Our dependence on any single third-party supplier increases when our supply of a particular service is more heavily concentrated with that third-party.~~ Some of our strategic partners offer, or could offer, competing products and services or also work with our competitors, the likelihood of which may increase due to the ongoing shift toward remote work. As a result of these factors, many of our third-party partners may choose to develop or support alternative products and services in addition to, or in lieu of, our work ~~marketplace, either on their own or in collaboration with others, including our competitors.~~marketplace. If we are unsuccessful in establishing or maintaining our relationships with third parties on favorable terms, or if these relationships are not successful in improving our business, our ability to compete or to grow our total revenue could be impaired and our operating results may be adversely impacted. ~~Even if~~Moreover, material business changes by one or more of our third-party staffing providers could

negatively impact our business and financial results, including increased costs for clients or us, a diminished user experience, or the inability to offer the staffing provider services in one or more jurisdictions.

Users circumvent our work marketplace, which adversely impacts our business.

Our business depends on users transacting through our work marketplace. Despite our efforts to prevent them from doing so, users circumvent our work marketplace and engage with or take payment through other means to avoid the fees that we ~~are successful~~charge, and it is difficult or impossible to measure the losses associated with circumvention. Enhancements and changes we make with respect to our pricing model, fees, offerings, services, and features may unintentionally cause, and may have unintentionally caused in ~~establishing~~the past, users to circumvent our work marketplace, such as our consolidation of our Upwork Basic and ~~maintaining these relationships with third parties on favorable terms, we cannot ensure that these relationships will result~~Upwork Plus offerings into our Client Marketplace Offering in ~~increased usage~~April 2022. In addition, circumvention by users of our work marketplace is likely to increase during a macroeconomic downturn, as users may be more cost-sensitive with respect to our fees. The loss of revenue associated with circumvention of our work marketplace has an adverse impact on our business, cash flows, operating results, and financial condition. Moreover, certain changes we make to decrease circumvention by users have in the past and could again inadvertently result in user dissatisfaction, increased user circumvention, and a decline in user activity on our work marketplace. Our efforts to reduce circumvention may be costly or ~~increased revenue. See~~disruptive to implement, have results that are difficult or impossible to measure, fail to have the ~~risk factor titled “If~~intended effect or have an adverse effect on our brand or user experience, reduce the attractiveness of our work marketplace, divert the attention of management, or otherwise harm our business.

Clients sometimes fail to pay their invoices, necessitating action by us to compel payment.

In connection with our Upwork Enterprise offering, and for certain legacy clients, we ~~are unable~~advance payments to talent for invoiced services on behalf of the client and subsequently invoice the client for such services. In order to maintain these relationships, we have in the past been, and may in the future be, forced to agree to terms that are unfavorable to us, including extended payments terms. In addition, in certain instances, we will advance payment on a talent invoice if the client issues a chargeback or their payment method is declined. In this circumstance, the talent assigns us the right to recover any funds from the client. From time to time, clients fail to pay for services rendered by talent, and as a result, we may incur costs to enforce the applicable agreement or our terms of service, including through arbitration or litigation, and we may not be successful in collecting amounts owed. Furthermore, some clients may seek bankruptcy protection or other similar relief and fail to pay amounts due, or pay those amounts more slowly, either of which could adversely affect our operating results, financial position, and cash flow. Our risk of financial exposure increases if we do not adequately screen clients, do not conduct sufficient credit checks, or otherwise do not adequately monitor clients’ spend on our work marketplace. All of these risks are made more likely during a macroeconomic downturn and could result in increased costs to us as we advance payments to talent and seek to compel payment ~~partner relationships on favorable terms, or at all,~~from our clients. Our failure to manage these risks could adversely affect our business, ~~could~~operating results, and financial condition.

We are subject to disputes with or between users of our work marketplace.

premium offerings, we disclaim responsibility and liability for any disputes between users (except with respect to specified dispute assistance programs and services); however, we cannot guarantee that these terms will be effective in preventing or limiting our involvement in user disputes or that these terms will be enforceable or otherwise effectively prevent us from incurring liability as a result of disputes between users. Disputes between clients and talent and between users and our company may become more frequent based on conditions outside our control, such as a macroeconomic downturn or actions of bad actors seeking to take advantage of other users. Such disputes, or any increase in the number of disputes, may result in an adverse effect on our company, such as a loss of goodwill with users, reputational harm, lost GSV and revenue, diversion of the resources of our management and an increase in our operational costs, any of which may adversely ~~affected” for additional information.~~affect our business and operating results.

Our business depends largely on our ability to attract and retain talented employees, including senior management and key personnel. If we lose the services of Hayden Brown, our President and Chief Executive Officer, or other members of our senior management team or key personnel, we may not be able to execute on our business strategy.

Our future success depends in large part on the continued services of senior management and other key personnel and our ability to attract, retain, and motivate them. In particular, we are dependent on the services of Hayden Brown, our President and Chief Executive Officer, and our future vision, strategic direction, work marketplace, and technology could be compromised if she were to take another position, become ill or incapacitated, or otherwise become unable to serve as our President and Chief Executive Officer. We rely on our leadership team and other key personnel in the areas of product, engineering, operations, security, marketing, sales, support, corporate development, and general and administrative functions. Our senior management and other key personnel are all employed on an at-will basis, which means that they could terminate their employment with us at any time, for any reason, and without notice, and we do not maintain any “key-person” life insurance policies. If we lose the services of senior management or other key personnel, if our succession plans prove inadequate, or if we are unable to retain, attract, train, and integrate the highly skilled personnel we need, our business, operating results, and financial condition could be adversely affected.

There have been, and may continue to be, changes in our management team resulting from the hiring or departure of ~~executives. For example, in September 2022,~~executives, and we ~~announced that we had initiated a search for a new Chief Financial Officer and that Jeff McCombs, our Chief Financial Officer, will be separating from Upwork. We~~ have made, and may continue to make, other changes that have been and will be disruptive to our personnel, such as changes to the composition of our leadership team and other key personnel and reorganizations of reporting lines of our workforce. For example, in May 2023, we announced that Eric Gilpin, our Chief Sales Officer, will depart from Upwork in the second quarter of 2023. These changes have resulted, and future personnel changes may result, in increased attrition or reduced productivity of our personnel, including senior management and key personnel, stemming from organizational restructuring, as new reporting relationships are established, and as other companies may increasingly target our executives and other key personnel, particularly during the current highly competitive market for qualified personnel. Any such changes may also result in a loss of institutional knowledge, cause disruptions to our business,

impede our ability to achieve our objectives, or distract or result in diminished morale in, or the loss of, workers.

Our future success also depends on our continuing ability to retain, attract, train, and integrate highly skilled personnel, including software engineers and sales personnel. We face intense competition for qualified personnel from numerous software and other technology companies. In addition, competition for qualified software engineers is particularly intense. This competition has become exacerbated by the increase in employee resignations currently taking place throughout the United States as a result of the COVID-19 pandemic, which is commonly referred to as the “great resignation.” We may not be able to retain our current key personnel or attract, train, integrate, or retain other highly skilled personnel in the ~~future, all of which may be more difficult given our shift to a flexible work model for our workforce.~~future. We may incur significant costs to attract and retain highly skilled personnel, we may lose employees to our competitors or other technology companies before we realize the benefit of our investment in recruiting and training them, and our succession plans may be insufficient to ensure business continuity if we are unable to retain key personnel or were to lose a significant portion of our personnel. Further, even highly skilled personnel may fail to be productive, and our adoption of remote work may result in a loss of productivity of our workforce. To the extent we move into new geographies, including internationally, we would need to attract and recruit skilled personnel in those areas.

Volatility, depreciation, or lack of appreciation in our stock price may also affect our ability to attract new skilled personnel and retain our key personnel. The market price of our common stock has ~~been,~~depreciated significantly recently and may continue to be ~~particularly~~ volatile, in part due to broader macroeconomic conditions and stock market fluctuations, and as a result, the equity held by our senior management and other key personnel ~~may have~~has depreciated in value relative to the ~~original purchase or issue price~~grant date value and therefore ~~have~~has less retentive power. If we are unable to attract and retain suitably qualified individuals who are capable of meeting our growing technical, operational, and managerial requirements, on a timely basis or at all, or if we need to increase our compensation expense to retain our employees, our business, operating results, financial condition, and cash flows may be adversely affected.

~~Clients sometimes fail to pay their invoices, necessitating action by us to compel payment.~~

In connection with our Upwork Enterprise offering, and for certain legacy clients, we advance payments to talent for invoiced services on behalf of the client and subsequently invoice the client for such services. In order to maintain these relationships, we have in the past been, and may in the future be, forced to agree to terms that are unfavorable to us, including extended payments terms. In addition, in certain instances, we will advance payment on a talent invoice if the client issues a chargeback or their payment method is declined and the talent assigns us the right to recover any funds from the client. From time to time, clients fail to pay for services rendered by talent, and as a result, we may be adversely affected both from the inability to collect amounts due and the cost of enforcing the applicable agreement or our terms of service, including through arbitration or litigation. For example, we have recently experienced a significant increase in our allowance for doubtful accounts as of September 30, 2022, as compared to prior periods. Clients’ failure to pay is increased if we do not adequately screen potential Enterprise or other clients, do not conduct sufficient credit checks, or otherwise do not adequately monitor clients’ spend on our work marketplace. Furthermore, some clients may seek bankruptcy protection or other similar relief and fail to pay amounts due, or pay those amounts more slowly, either of which could adversely affect our operating results, financial position, and cash flow. All of these risks are made more likely during a macroeconomic downturn and could result in increased costs to us as we advance payments to talent and seek to compel payment from our clients.

~~We are subject to disputes with or between users of our work marketplace.~~

Our business model involves enabling connections between talent and clients that contract directly through our work marketplace. Talent and clients are free to negotiate any contract terms they choose, but we also provide optional service contract terms that they can elect to use. Disputes sometimes arise between talent and clients with regard to their contract terms, work relationship, or otherwise, including with respect to service standards, payment, confidentiality, work product, and intellectual property ownership and infringement. If either party believes the contract terms were not met, including as a result of actions of bad actors seeking to take advantage of other users, our standard terms and some individually negotiated services agreements provide a mechanism for the parties to request assistance from us, and, for some contracts, if that is unsuccessful, they may choose to resolve the dispute with the help of a third-party arbitrator. Whether or not talent and clients decide to seek assistance from us, if these disputes are not resolved amicably, the parties might escalate to formal proceedings, such as by filing claims with a court or arbitral authority. Given our role in facilitating and supporting these arrangements, claims are sometimes brought against us directly as a result of these disputes and talent or clients bring us into any claims filed against each other, particularly when the other user is insolvent or facing financial difficulties. Through our terms of service and services agreements for premium offerings, we disclaim responsibility and liability for any disputes between users (except with respect to specified dispute assistance programs and services); however, we cannot guarantee that these terms will be effective in preventing or limiting our involvement in user disputes or that these terms will be enforceable or otherwise effectively prevent us from incurring liability as a result of disputes between users. In addition, from time to time users assert claims against us regarding their experience on our work marketplace, including related to their search ranking results, their feedback ratings, our advertising or marketing, our dispute resolution process, or admission or non-admission to our work marketplace or other programs and badges, including those designed for highlighting successful talent. Moreover, for some premium offerings, we provide enhanced services and assistance with respect to disputes over work product, and clients or talent may pursue claims against us if they are not satisfied with those enhanced services. Disputes between clients and talent and between users and our company may become more frequent based on conditions outside our control, such as a macroeconomic downturn or actions of bad actors seeking to take advantage of other users. Such disputes, or any increase in the number of disputes, may result in an adverse effect on our company, such as a loss of goodwill with users, reputational harm, lost GSV and revenue, and an increase in our operational costs. Even if these claims do not result in litigation or are resolved in our favor, these claims, and the time and resources necessary to resolve them, could: result in legal, settlement, or other financial costs; divert the resources of our management; and adversely affect our business and operating results.

We may be unable to integrate acquired businesses and technologies successfully or to achieve the expected benefits of such acquisitions. We may acquire or invest in additional companies, which may divert our management’s attention, result in additional dilution to our stockholders, and consume resources that are necessary to sustain our business.

Our business strategy may, from time to time, include acquiring complementary products, technologies, businesses, or other assets. We also may enter into relationships with other businesses to expand our work marketplace or our ability to provide our work marketplace in foreign jurisdictions, which could involve preferred or exclusive licenses, additional channels of distribution ~~discount pricing,~~ or investments in other companies. Negotiating these transactions can be time-consuming, difficult, and expensive, and our ability to close these transactions may often be subject to approvals that are beyond our control. Consequently, these transactions, even if undertaken and announced, may not close, and any acquisition, investment, or business relationship may result in unforeseen or additional operating difficulties, risks, and expenditures. For one or more of those transactions, we may:

•use cash that we may need in the future to operate our business;

•become subject to different laws and regulations due to the nature or location of the acquired business, products, technologies, or other assets, or become subject to more stringent scrutiny or

differing applications of laws and regulations to which we are currently subject as a result of such transactions;

•issue additional equity or convertible debt securities that would dilute our stockholders’ ownership interest;

•incur expenses or assume substantial liabilities;

•encounter difficulties retaining key personnel of the acquired company or ~~integrating diverse software codes, operations, or business cultures;~~

•~~encounter difficulties in~~ assimilating acquired operations and ~~development~~employee cultures or otherwise fail to realize the anticipated benefits of such transactions;

•encounter ~~diversion of~~difficulties integrating diverse cloud, software, and other information technology platform technologies;

•divert management’s ~~attention to other business concerns;~~attention;

•become subject to adverse tax consequences, substantial depreciation, or deferred compensation charges;

•incur debt on terms unfavorable to us or that we are unable to repay; or

•be required to adopt new, or change our existing, accounting policies.

Any of these risks could adversely impact our business and operating results.

Risks Related to Our Industry, Offerings, and Services

Our inability to generate revenue from our marketplace offerings, which represents a substantial majority of our total revenue, would adversely affect our business operations, financial results, and growth prospects.

We derive, and expect to continue to derive in the near future, the substantial majority of our revenue from our marketplace offerings. As such, market acceptance of our marketplace offerings, including new offerings or the consolidation of offerings, such as our consolidation of our Upwork Basic and Upwork Plus offerings into our ~~new~~ Client Marketplace offering in April 2022, is critical to our continued ~~success,~~success. If we are unable to meet user demands and ~~any failure~~expectations, earn and maintain user trust, expand our offerings or

the categories of services offered on our work marketplace, develop features that are appealing to users, or achieve and maintain more widespread market acceptance of our marketplace offerings, ~~to meet users’ expectations with respect to user experience, trust, or cost or the failure of specific features to be effective in~~including attracting and retaining ~~users~~clients, our business operations, financial results, and growth prospects will ~~have a negative impact on our business.~~ be adversely affected.

Demand for our marketplace offerings is also affected by a number of other factors, including the timing and success of new offerings and services by our competitors, our ability to respond to technological change and to effectively innovate and grow, macroeconomic conditions, contraction in our market, client spending patterns, talent activity levels, the size and price of projects on our work marketplace, changes in adoption of remote work, including as the COVID-19 pandemic subsides, geopolitical events, such as ~~Russia’s invasion of~~the war in Ukraine and the ~~economic measures~~ resulting ~~from the invasion,~~ macroeconomic effects, ~~such as~~ de-globalization, ~~and the current macroeconomic uncertainty, and impacts resulting from the COVID-19 pandemic,~~, and the other risks identified herein. ~~For example,~~To the extent these or other factors negatively affect demand for our marketplace offerings, our financial results may be adversely affected.

If the market for independent talent and the services they offer develops more slowly than we ~~experienced~~expect, our growth may slow or stall, and our operating results could be adversely affected.

The market for online independent talent and the services they offer is relatively new, rapidly evolving, and unproven. Our future success will depend in large part on the continued growth and expansion of this market and the willingness of businesses to engage independent talent to provide services and independent talent to engage as service providers. It is difficult to predict the size, growth rate, and expansion of this market, whether any expansion will be long-term or temporary, particularly as the labor market and remote work trends continue to be unpredictable, global and U.S. economies are at risk of recession, the success of competitive products and services, or technological (including artificial intelligence), macroeconomic, geopolitical (including the prevalence of de-globalization), legal, regulatory, or other developments that will impact the overall demand for, or ability to engage, independent talent. Furthermore, many businesses may be unwilling to engage independent talent for a ~~quarter-over-quarter decline in GSV~~variety of reasons, including perceived negative connotations with outsourcing work, quality of work, fraud, privacy, or data security concerns, or the rapidly evolving regulations that may impact the demand for independent contractor services more generally, including as discussed further in the ~~third quarter~~risk factor titled “The regulatory landscape regarding contractor classification is rapidly changing and changes in these laws could adversely affect demand for our services and work marketplace and adversely affect our business. In addition, there may be adverse tax, legal, and other consequences if the contractor classification or employment status of ~~2022~~talent that was attributable in part to seasonal and weakening macroeconomic conditions. If we are unable to meet user demands, earn and maintain user trust, expand our offerings or the categories of services offered onuse our work marketplace is challenged.” Likewise, with the greater adoption of remote work and increased flexibility in employment relationships resulting from the COVID-19 pandemic, more skilled independent talent may choose traditional employment. If the market for independent talent and the services they offer does not achieve widespread adoption, or ~~achieve~~there is a reduction in demand for independent talent, including as a result of challenging macroeconomic conditions or as the COVID-19 pandemic subsides , it could result in decreased revenue and ~~maintain more widespread market acceptance of our marketplace offerings, including attracting and retaining clients,~~ our business ~~operations, financial results, and growth prospects will~~could be adversely affected.

If we fail to develop, maintain, and enhance our brand and reputation cost-effectively, our business and financial condition may be adversely affected.

We believe that developing, maintaining, evolving, and enhancing awareness and integrity of our brand and reputation in a cost-effective manner are important to achieving widespread acceptance and use of our work marketplace and are important elements in attracting new users and retaining existing users. Successful and efficient promotion and positioning of our brand, offerings, and business model depend on, among other things, the effectiveness of our marketing efforts and brand messaging, our ability to provide a reliable, trustworthy, and useful work marketplace and offerings at competitive prices, the perceived value of our work marketplace and offerings, and our ability to engender user trust and provide

quality support. In order to reach the brand awareness and acceptance levels of some of our competitors, we need to continuously invest in marketing programs that may not be successful in achieving meaningful awareness and acceptance levels, particularly during early phases of expansion into newer user awareness segments, such as international users and users who are reluctant to utilize remote or contract workers. ~~Some of the marketing programs and brand promotion efforts we implement may be new and unproven and therefore their likelihood of success may be uncertain.~~ Further, our brand promotion activities may not resonate with existing or potential users or yield increased revenue, and even if they do, the increased revenue may not offset the expenses we incur in building, evolving, and maintaining our brand and reputation. For example, sincebe effective. Since 2019, we have made

significant investments in sales and marketing to acquire new clients and drive brand awareness, and expect to increase these investments throughout 2022. It is not certain that these investments have had or will have sufficient positive impact on our brand to be cost effective. Likewise, negative publicity and news coverage, fraud or other illegal activity conducted by bad actors on our work marketplace, or decisions we make relating to geopolitical or social matters, such as our decision to suspend business operations in Russia and Belarus, may undermine our brand promotion efforts or harm our reputation. We have also recently evolved, and will continue to evolve, our marketing and brand positioning efforts, including a rebranding effort which we began in the second quarter of 2021, ~~expanding our focus~~we launched a rebranding effort. This rebranding effort focused on large enterprise and other clients and prospects with larger, longer-term independent talent needs. More recently, in the third quarter of 2022, we launched a new brand campaign, advertising across television, online video, streaming audio, and digital and social media channels. ~~These efforts may~~It is not certain that these and any future investments have had or will have sufficient positive impact on our brand to be ~~successful~~cost effective. For example, we announced in ~~achieving the brand awareness and acceptance levels in a cost-effective manner, or without harming other areas~~May 2023 as part of our ~~business.~~

~~We also rely on~~efforts to reduce spend and streamline operations a reduction in our ~~community~~levels of ~~users~~investments in ~~a variety of ways, including their willingness to give us feedback regarding our work marketplace,~~brand awareness. Likewise, negative publicity and ~~failure of our users to provide feedback on their experience~~news coverage, fraud, or other illegal activity conducted by bad actors on our work marketplace, or decisions we make relating to geopolitical or social matters, may undermine our ~~failure to adequately assess user satisfaction with~~brand promotion efforts or harm our work marketplace or address any concerns could negatively impact our ability to improve our work marketplace and the willingness of current or prospective users to use our work marketplace. For example, the prior changes made in the pricing and packaging of Connects purchases resulted in user dissatisfaction and negatively impacted fill rates for projects on our work marketplace for a period of time.reputation. If we fail to promote and maintain our brand successfully, address user concerns, or to maintain loyalty among our users, or if we incur substantial expenses in unsuccessful attempts to promote and maintain our brand, we may fail to attract new users or retain our existing users and our business and financial condition may be adversely affected.

If ~~the market for independent talent~~we are not able to develop and ~~the~~release new offerings and services, ~~they offer develops more slowly than we expect,~~or develop and release successful enhancements, new features, and modifications to our ~~growth may slow or stall,~~existing offerings and services, our ~~operating results~~business could be adversely affected.

The market for online independent talent and the services they offer is relatively new, rapidly evolving, and unproven. Our future success will depend in large part on the continued growth and expansion of this market and the willingness of businesses to engage independent talent to provide services and independent talent to engage as service providers. It is difficult to predict the size, growth rate, and expansion of this market, whether any expansion will be long-term or temporary, particularly as the COVID-19 pandemic subsides and restrictions intended to prevent its spread are relaxed or lifted, the labor market continues to be unpredictable, global and U.S. economies are at risk of recession, the success of competitive products and services, or technological, macroeconomic, geopolitical (including the prevalence of de-globalization), legal, regulatory, or other developments that will impact the overall demand for, or ability to engage, independent talent. For example, we experienced a quarter-over-quarter decline in GSV in the third quarter of 2022 that was attributable in part to seasonal and weakening macroeconomic conditions. Furthermore, many businesses may be unwilling to engage independent talent for a variety of reasons, including perceived negative connotations with outsourcing work, quality of work, fraud, privacy, or data security concerns, or the rapidly evolving regulations that may impact the demand for independent contractor services more generally, including as discussed further in the risk factor titled “There may be adverse tax, legal, and other consequences if the contractor classification or employment status of talent that use our work marketplace is ~~challenged.” Likewise,~~characterized by rapid technological change, frequent product and service introductions and enhancements, changing user demands, and evolving industry standards. The introduction of offerings and services embodying new technologies can quickly make existing offerings and services obsolete and unmarketable. We invest substantial resources in researching and developing new offerings and services and enhancing our work marketplace by incorporating additional features, improving functionality, modernizing our technology, and adding other improvements to meet our users’ evolving demands in our increasingly highly competitive industry. The success of any enhancements or improvements to, or new features of, our work marketplace or any new offerings and services depends on several factors, including overall demand and market acceptance consistent with the ~~greater adoption~~intent of ~~remote~~such offerings or services, competitive pricing, adequate quality testing to ensure an absence of errors, defects, and disruptions on our work marketplace, integration with new and ~~increased flexibility~~existing technologies on our work marketplace and third-party partners’ technologies, and timely completion. We cannot be sure that we will succeed, on a timely or cost-effective basis, in ~~employment relationships resulting from the~~

~~COVID-19 pandemic, more skilled independent talent may choose traditional employment. If~~developing, marketing, and delivering enhancements or new features to or modernizing our work marketplace or any new offerings and services that respond to continued changes in the market for independent talent or business services. Any enhancements or new features to our work marketplace or any new offerings and ~~the~~ services ~~they offer does~~may not achieve, ~~widespread adoption,~~and in the past certain features and offerings have not achieved, market acceptance, cost-effectiveness, or ~~there~~the intended effect. In the past, we have experienced unintended negative effects, including reduced client spend, diminished fill rates for projects on our work marketplace, errors and disruptions on our work marketplace, and user dissatisfaction from certain modifications to our offerings, services, and features.

Moreover, even if we introduce new offerings and services, we may experience a decline in revenue from our existing offerings and services that is ~~a reduction in demand for independent talent, including as~~not offset by revenue from the ~~COVID-19 pandemic subsides~~new offerings or ~~as a result of a macroeconomic downturn, it~~services. In addition, we may lose existing users that choose to use competing products or services. This could result in ~~decreased~~a temporary or permanent decrease in revenue and adversely affect our ~~business could be adversely affected.~~business.

We face intense competition and could lose market share to our competitors, which could adversely affect our business, operating results, and financial condition.

The market segment for independent talent and the clients that engage them is highly competitive, rapidly evolving, fragmented, and subject to changing technology, shifting needs, and frequent introductions of new competitors as well as new offerings and services. The level of competition within, and the frequency and likelihood of increased third-party investment and new competitors entering, this market segment has further intensified due to the ongoing COVID-19 pandemic and the resulting shift toward remote work and other labor market dynamics. We compete with a number of online and offline platforms and services domestically and internationally, as well as traditional staffing firms, to attract and retain users and expand our share of user spend. Our main competitors fall into the following categories:

•traditional contingent workforce and staffing service providers and other outsourcing providers, such as The Adecco Group, Randstad, Recruit, Allegis Group, and Robert Half International;

•online freelancer platforms that serve either a diverse range of skill categories, such as Fiverr, Guru, and Freelancer.com, or specific skill categories;

•other online providers of products and services for individuals or businesses seeking work or to advertise their services, including personal and professional social networks, such as LinkedIn and GitHub (each owned by Microsoft), employment marketplaces, platforms providing compliance services, recruiting websites, and project-based deliverable providers;

•software and business services companies focused on talent acquisition, management, invoicing, or staffing management products and services, such as Workday;

•payment businesses that can facilitate payments to and from businesses and service providers, such as PayPal and Payoneer;

•businesses that provide specialized professional services, including consulting, accounting, marketing, and information technology services; and

•online and offline job boards, classified ads, and other traditional means of finding work and service providers, such as Craigslist, CareerBuilder, Indeed, Monster, and ZipRecruiter.

In addition, well-established internet companies, such as Google, LinkedIn, and Amazon, social media platforms, such as Meta, and businesses that operate driving, delivery, and other commoditized marketplaces, such as Uber Technologies, have entered or may decide to enter ~~into~~ our market segment. Some of these companies have launched or may launch, or have acquired or may acquire companies or assets that offer products and services that directly compete with our work marketplace. For example, LinkedIn launched ProFinder in 2016, Open for Business in 2019, and Services Marketplaces in 2021, each of which is a service to connect LinkedIn members with one another for freelance service relationships. Many of these established internet companies and other competitors are considerably larger than we are, have considerably greater financial and other resources than we do, and could offer products and services similar to our offerings for lower fees.

Internationally, we compete against online and offline channels and products and services in most countries. Local competitors, or competitors that have invested more in international expansion, have greater brand recognition than us in other countries and a stronger understanding of local or regional culture and commerce. Some competitors also offer their products and services in local languages and currencies that we do not offer. As our business grows internationally and we expand and grow our services offerings, we may increasingly compete with these international companies. We also compete against locally sourced service providers and traditional, offline means of finding work and procuring

services, such as staffing businesses, personal and professional networks, classified ads, and recruiters. In addition, our decision to suspend our business operations in Russia and Belarus may increase the risk that new competitors emerge in the region.

We also compete with companies that utilize emerging technologies and assets, such as blockchain, artificial intelligence, augmented reality, cryptocurrency, and machine learning. These competitors may offer products and services that may, among other things, provide automated alternatives to the services that talent provide on our work marketplace, use machine learning algorithms to connect businesses with service providers more effectively than we do, or otherwise change the way that businesses engage or pay service providers or the way service providers perform work so as to make our work marketplace less attractive to users. ~~Many of the companies and services that utilize these technologies in our market are still new and not yet fully mature in their capabilities or network scale; however, we~~We may face increased competition ~~should~~from these ~~companies~~competitors as they mature and expand their capabilities.

Internationally, we compete against online and offline channels and products and services in most countries. Local competitors, or competitors that have invested more in international expansion, have greater brand recognition in other countries and a stronger understanding of local or regional culture and commerce. Some competitors also offer their products and services orin local languages and currencies that we do not offer. As our business grows internationally and we expand and grow our services offerings, we may increasingly compete with these international companies. We also compete against locally sourced service providers and traditional, offline means of finding work and procuring services, such as staffing businesses, personal and professional networks, classified ads, and recruiters. In addition, our decision to suspend our business operations in Russia and Belarus in March 2022 may increase the risk that new ~~entrants, succeed.~~competitors emerge in the region.

Many of our current and potential competitors, both online and offline, enjoy substantial competitive advantages, such as: greater name recognition and more prominent brand reputation; pre-existing relationships with desirable clients; more experience with international operations and localization of their offerings; longer operating histories; greater financial, technical, and other resources; more users; newer technologies and more modern technical infrastructure; greater appeal to certain segments of users, such as those entering the workforce; and, in some cases, the ability to rapidly combine online platforms with traditional staffing and contingent worker solutions. These companies may use these advantages to offer

products and services similar to ours at a lower price, develop different or superior products and services to compete with our work marketplace, or respond more quickly and effectively than we do to new or changing opportunities, technologies, standards, regulatory conditions, or user preferences or requirements. In addition, while we compete intensely in more established markets, we also compete in developing technology markets that are characterized by dynamic and rapid technological change, many and different business models, and frequent disruption of incumbents by innovative online and offline entrants. The barriers to entry into these markets can be low, and businesses easily and quickly can launch online or mobile platforms and applications at nominal cost by using commercially available software or partnering with various established companies in these markets.

Moreover, current and future competitors may also make strategic acquisitions or establish cooperative relationships among themselves or with others, including our current or future third-party partners. By doing so, these competitors may increase their ability to meet the needs of our existing or prospective users. These developments could limit our ability to obtain revenue from existing and new users. For all of these reasons, we may not be able to compete successfully against our current and future competitors, in which case our business, operating results, and financial condition would be adversely impacted.

If we are not able to develop and release new offerings and services, or develop and release successful enhancements, new features, and modifications to our existing offerings and services, our business could be adversely affected.

The market for our work marketplace is characterized by rapid technological change, frequent product and service introductions and enhancements, changing user demands, and evolving industry standards. The introduction of offerings and services embodying new technologies can quickly make existing offerings and services obsolete and unmarketable. We invest substantial resources in researching and developing new offerings and services and enhancing our work marketplace by incorporating additional features, improving functionality, modernizing our technology, and adding other improvements to meet our users’ evolving demands in our increasingly highly competitive industry. For example, in 2020 we invested a significant amount of resources to launch Project Catalog and we continue to invest resources to modify and enhance this and other offerings to increase client traffic and usage and improve the user experience. The success of any enhancements or improvements to, or new features of, our work marketplace or any new offerings and services, such as Project Catalog, depends on several factors, including overall demand and market acceptance consistent with the intent of such offerings or services, competitive pricing, adequate quality testing to ensure an absence of errors, defects, and disruptions on our work marketplace, integration with new and existing technologies on our work marketplace and third-party

partners’ technologies, and timely completion. We cannot be sure that we will succeed, on a timely or cost-effective basis, in developing, marketing, and delivering enhancements or new features to or modernizing our work marketplace or any new offerings and services that respond to continued changes in the market for independent talent or business services. Any enhancements or new features to our work marketplace or any new offerings and services may not achieve, and in the past certain features and offerings have not achieved, market acceptance, cost-effectiveness, or the intended effect. In the past, we have experienced unintended negative effects, including reduced client spend, diminished fill rates for projects on our work marketplace, errors and disruptions on our work marketplace, and user dissatisfaction from certain modifications to our offerings, services, and features.

Moreover, even if we introduce new offerings and services, we may experience a decline in revenue from our existing offerings and services that is not offset by revenue from the new offerings or services. In addition, we may lose existing users that choose to use competing products or services. This could result in a temporary or permanent decrease in revenue and adversely affect our business.

If we or our third-party partners experience a security breach, other hacking or phishing attack, ransomware or other malware attack, or other privacy or security incident, whether intentionally or unintentionally caused by us or by third parties, our work marketplace may be perceived as not being secure, our reputation may be harmed, demand for our work marketplace may be reduced, our operations may be disrupted, we may incur significant legal costs, fines, or liabilities, and our business could be adversely affected.

Our business involves the storage, processing, and transmission of users’ proprietary, confidential, and personal information as well as the use of third-party partners and vendors who store, process, and transmit users’ proprietary, confidential, and personal information. We also maintain and use third-party partners and vendors who process certain other proprietary and confidential information relating to our business and personal information of our personnel. Our systems, and the systems of our vendors and third-party partners, may be vulnerable to privacy or security incidents, such as computer viruses and other malicious software, physical or electronic break-ins, or vulnerabilities resulting from intentional or unintentional service provider actions, and similar disruptions that could make all or portions of our website or applications unavailable for periods of time. Any privacy or security incident, whether intentionally or unintentionally caused by us or by third parties, including government agencies, that we experience could result in: unauthorized access to, misuse of, or unauthorized acquisition of our, our personnel’s, or our users’ data; the loss, corruption, or alteration of this data; interruptions in our operations; or damage to our computers or systems or those of our users. Any of these could expose us to claims, litigation, fines, enforcement actions, other potential liability, and reputational harm. Additionally, ransomware or other malware, viruses, social engineering (including business email compromise and related wire-transfer fraud), impersonation of our company and executives on social media, and general hacking in our industry have become more prevalent and more complex. Bad actors often try to take advantage of us, our users, and our vendors and third-party partners by using social engineering and other methods to persuade their victims to make fraudulent payments, or to download viruses, ransomware, or other malware into computer systems and networks. Because the techniques used to obtain unauthorized access, disable or degrade service, or sabotage systems change frequently and often are not foreseeable or recognized until launched against a target, we and our vendors and third-party partners may be unable to anticipate these techniques or to implement adequate preventative measures, despite our efforts to implement and maintain a robust information security program. There may also be increased risk of privacy or security incidents as a result of the effects of the war in Ukraine and our ongoing operational decisions related to the suspension of our business in Russia and Belarus in March 2022. Data security breaches and other privacy and security incidents may also result from non-technical means, such as ~~for example,~~ actions taken by employees or contractors, ~~such as~~including talent that we engage on our work marketplace to perform services for us, and the likelihood of such incidents may increase as a result of our workforce working remotely. We may also integrate generative artificial intelligence tools into our platform and products, or our vendors may in turn incorporate generative artificial intelligence tools

into their own offerings, and the providers of these generative artificial intelligence tools may not meet existing or rapidly evolving regulatory or industry standards with respect to data privacy and protection, and may inhibit our or our vendors’ ability to maintain an adequate level of service and experience. If we, our vendors, or our third-party partners experience an actual or perceived breach or privacy or security incident, public perception of the effectiveness of our security measures and brand could be harmed, and we could lose users and business. In addition, significant unavailability of our work marketplace due to security breaches or other privacy and security incidents could cause users to decrease their use of or cease using our work marketplace. Any of these effects could adversely impact our business.

Any compromise of our security or the security of our vendors, third-party partners, or users could result in regulatory or other governmental investigations, enforcement actions, litigation, and legal and financial exposure, including potential regulatory fines or penalties or contractual liability. We may also need to expend significant resources to protect against, and to address issues created by, security breaches and other privacy and security incidents. While we maintain cyber liability insurance, these liabilities may exceed the amounts covered by our insurance; further, we cannot be certain that our insurance coverage will extend to or be adequate for liabilities actually incurred, or that insurance will continue to be available to us on economically reasonable terms, at coverage limits we deem prudent, or at all. Any such compromise could also result in damage to our reputation and a loss of confidence in our security measures.

Depending on the nature of the information compromised, in the event of a security breach or other privacy or security incident, we may also have obligations to notify affected individuals and entities and regulators about the incident, and we may need to provide some form of remedy, such as a subscription to credit monitoring services, pay significant fines to one or more regulators, reimburse, defend or indemnify third parties if required under contractual obligations, or pay compensation in connection with a class-action settlement (including under the private right of action under the California Consumer Privacy Act of 2018, which we refer to as the CCPA). Such breach notification laws continue to evolve and may be inconsistent from one jurisdiction to another. Complying with these obligations could cause us to incur substantial costs and could increase negative publicity surrounding any incident that compromises our, our users’, our employees’, our contractors’, or other confidential, proprietary, or personal information.

Because a substantial portion of the services offered by talent and sought by clients on our work marketplace is information technology services, a decline in talent offering information technology services or the market for information technology service providers on our work marketplace could adversely affect our business.

A substantial portion of the services offered by talent and sought by clients on our work marketplace relates to information technology. If, for any reason, the market for information technology services declines, including as a result of the relaxation or lifting of restrictions intended to prevent the spread of COVID-19, a macroeconomic downturn, increased use of artificial intelligence or automation, or otherwise, if a sufficient number of qualified or desirable talent is not available on our work marketplace or willing to perform these services or businesses satisfy their needs for these services through alternative means, including through use of our competitors’ products or traditional employment relationships, or if the talent on our work marketplace are not located or able to work in specific geographic regions in which clients are seeking to engage remote talent, the growth in the number of users on our work marketplace may slow or decline and as a result our revenue and business may be adversely impacted. Geopolitical events have impacted and may continue to impact the market for information technology services on our work marketplace. For example, approximately 25% of client spend from our web, mobile, and software development category in 2021 was derived from work where either the talent or the client was located in the region impacted by Russia’s invasion of Ukraine, and immediately following the beginning of the invasion, we experienced meaningful reductions in activity from talent in the region.

Our sales efforts are ~~increasingly~~ primarily targeted at large enterprise and other clients and prospects with larger, longer-term independent talent needs, and as a result we may encounter greater pricing, implementation, and customization challenges, and we may incur additional costs, each of which could adversely impact our business and operating results.

Our sales efforts are primarily targeted at large enterprise and other clients and prospects with larger, longer-term independent talent needs. For example, since the fourth quarter of 2021, we have increased our investment in sales by expanding our sales team and support personnel and we expect this investment to continue through the remainder of 2022 as we increase our efforts to acquire clients of our Upwork Enterprise offering. As a result of our ~~increased~~ focus on these larger clients, we face greater costs, longer sales cycles, and less predictability in completing some of our sales and in increasing spend by existing clients. In addition, our acquisition of new clients of our Upwork Enterprise offering has slowed recently, driven primarily by elongated sales cycles due to the ~~current~~persistent macroeconomic ~~conditions and certain internal operational challenges, we experienced longer sales cycles and acquired fewer Upwork Enterprise clients~~

~~in the third quarter of 2022 compared with the prior period in 2021 and the second quarter of 2022.~~headwinds. For larger clients, use of our work marketplace may require approvals by multiple departments and executive-level personnel and require us to provide greater levels of services and client education regarding the uses, benefits, security, privacy, worker classification, payments, and compliance services offered on our work marketplace. Larger enterprises typically have longer decision-making and implementation cycles and demand more customization, greater indemnification and risk shifting, higher levels of support, a broader range of services, and greater payment flexibility. In addition, larger clients may require greater functionality and scalability that can lead to delays in sales or difficulties in growing client spend. We are often required to spend time and resources to better familiarize potential large enterprise clients with the value propositions of our work marketplace generally. Despite our efforts in familiarizing potential large enterprise clients with the benefits of our work marketplace, these potential clients may decide not to use our work marketplace if, among other reasons, they do not feel that their procurement or compliance needs are or will be met or our work marketplace is not widely accepted within the organization. In addition, sales opportunities with large clients may require us to devote greater sales and administrative support and professional services resources to individual clients, which could increase our costs, lengthen our sales cycle, and divert our own sales and professional services resources to a smaller number of

larger clients. We may spend substantial time, effort, and money in our sales efforts without being successful in producing sales or growing client spend.

~~Even if we reach an agreement with a client to use our work marketplace, the agreement may not be on pricing or other terms that are favorable to us.~~ A significant portion of the fees we typically receive from clients is contingent on the level of spend by the client. If a client ~~negotiates pricing terms that are less favorable to us,~~ does not engage talent on our work marketplace, or uses talent for few projects or projects of low value, our revenue from the relationship may be minimal.

~~Users circumvent our work marketplace, which adversely impacts our business.~~

~~Our business depends~~Because a substantial portion of the services sought by clients and offered by talent on users transacting through our work marketplace. Despite our efforts to prevent them from doing so, users circumvent our work marketplace and engage with or take payment through other means to avoid the fees that we charge, and it is difficult or impossible to measure the losses associated with circumvention. Enhancements and changes we make with respect to our offerings, services, features, pricing model, and fees may unintentionally cause, and may have unintentionally caused in the past, users to circumvent our work marketplace, such as our consolidation of our Upwork Basic and Plus offerings into our new Client Marketplace Offering. In addition, circumvention by users of our work marketplace is ~~likely~~information technology services, a decline in client demand for, or talent offering, information technology services on our work marketplace could adversely affect our business.

A substantial portion of the services sought by clients and offered by talent on our work marketplace relates to ~~increase during a macroeconomic downturn, as users may be more cost-sensitive with respect to our fees. There may also be increased circumvention~~information technology. If, for any reason, the market for information technology services declines, including as a result of challenging macroeconomic conditions, as the ~~effects~~COVID-19 pandemic subsides, as a result of ~~Russia’s invasion~~increased use of Ukraine and our decision to suspend our business operations in Russia and Belarus. Moreover, certain changes we make to decrease circumvention by users have in the past and could again inadvertently result in user dissatisfaction, increased user circumvention, andartificial intelligence or automation, or otherwise, if a ~~decline in user activity~~sufficient number of qualified or desirable talent is not available on our work ~~marketplace. The loss~~marketplace or willing to perform these services or businesses satisfy their needs for these services through alternative means, including through use of ~~revenue associated with circumvention of~~our competitors’ products or traditional employment relationships, or if the talent on our work marketplace ~~has an adverse impact~~are not located or able to work in specific geographic regions in which clients are seeking to engage remote talent, the growth in the number of users on our business, cash flows, operating results, and financial condition. In addition, our efforts to reduce circumvention may be costly or disruptive to implement, have results that are difficult or impossible to measure, fail to have the intended effect or have an adverse effect on our brand or user experience, cause users to cease using our work marketplace ~~reduce~~may slow or decline and as a result our revenue and business may be adversely impacted. Geopolitical events have impacted and may continue to impact the ~~attractiveness of~~market for information technology services on our work ~~marketplace, divert the attention of management, or otherwise harm our business.~~marketplace.

If internet search engines’ methodologies or other channels that we utilize to direct traffic to our website are modified to our disadvantage, or our search result page rankings decline for other reasons, our user growth could decline.

We depend in part on various internet search engines, such as Google, as well as other channels to direct a significant amount of traffic to our website and mobile applications. Our ability to maintain the number of visitors directed to our website and mobile applications is not entirely within our control. For example, our competitors’ search engine optimization and other efforts such as paid search may result in their websites receiving a higher search result page ranking than ours, internet search engines or other channels that we utilize to direct traffic to our website have in the past and could again revise their

methodologies or implement other changes or penalties that adversely impact traffic to our website, or we may make changes to our website or mobile applications that adversely impact our search engine optimization rankings and traffic to our website and mobile applications in order to comply with applicable regulatory requirements or requirements imposed by our vendors or third-party partners, or for other reasons. As a result, links to our website may not be prominent enough to drive sufficient traffic to our website, and we may not be able to influence the results.

Search engines and other channels that we utilize to drive users to our website and mobile applications periodically change their algorithms, policies, and technologies, sometimes in ways that cause traffic to our website and mobile applications to decline. These changes can also result in an interruption in users’ ability to access our website, a drop in our search ranking, higher levels of low-intent traffic visiting our website and mobile applications, a misunderstanding among potential users regarding the functionality or purpose of our work marketplace, or have other adverse impacts that negatively affect our ability to maintain and grow the number of users that visit our website or mobile applications. We may also be forced to significantly increase marketing expenditures in the event that market prices for online advertising and paid listings escalate or our organic ranking decreases. Any of these changes could have an adverse impact on our business, user acquisition, and operating results.

Additionally, new and developing ~~U.S.~~ privacy laws have established individual rights with respect to personal information that may lead to downstream effects on our ability to realize and quantify the value of our marketing initiatives. As more jurisdictions adopt expansive data privacy regulatory requirements, an increasing number of users and website visitors will be afforded the right to opt-out of the sharing of their personal information for purposes of specific types of online advertising. The resulting decrease of individuals to whom we and our third-party marketing and advertising vendors and partners may employ

industry standard online advertising practices may lead to diminished efficacy of our marketing efforts, diminished visitor-to-user conversions, and increased costs of maintaining compliance.

Errors, defects, or disruptions in our work marketplace could diminish demand, adversely impact our financial results, and subject us to liability.

Our work marketplace enables our users to manage important aspects of their businesses, and any errors, defects, or disruptions in our work marketplace, or other performance or availability problems with our work marketplace or infrastructure could harm our brand and reputation, negatively impact our operating results, impair our ability to obtain or maintain licenses necessary to operate our business or deliver certain services, impair or jeopardize our partner relationships, or otherwise damage our business or the businesses of our users. As ~~the usage of our work marketplace grows, and as~~ we ~~introduce new offerings and services and look to~~ expand, ~~our international footprint over time,~~ we will need an increasing amount of technical infrastructure and continued infrastructure modernization, including network capacity, computing power, and improvements to how we process and store data and transaction ~~information, to continue to operate our work marketplace and offer certain services.~~information. We may fail to effectively scale and grow our technical infrastructure to accommodate these demands, which may adversely affect our user experience. We also rely on third-party software and infrastructure, including the infrastructure of the internet, to provide our work marketplace. Any failure of or disruption to this software and infrastructure could also make our work marketplace unavailable to our users. ~~For example, these~~These types of disruptions have ~~negatively impacted our work marketplace, such as an inadvertent error by a regulatory agency that prevented users from accessing our website for a brief period of time.~~occurred in the past and will likely occur in the future. Internet shutdowns in certain jurisdictions are becoming more frequent, including in response to civil unrest or prior to contested political elections, and any shutdown in a jurisdiction in which a significant number of our users are located will adversely affect user activity on our work marketplace throughout the duration of such shutdown. ~~Our~~

We also may have undetected errors in our system and work marketplace, ~~is constantly changing with~~including when new updates ~~which may contain undetected errors when~~are first introduced or released. Any errors, defects, disruptions in service, or other performance or stability problems with our work marketplace, or the inadequacy of our efforts to adequately prevent or timely detect or remedy errors or defects, could result in negative publicity, loss of or delay in market acceptance of our work marketplace, loss of competitive position, our inability to timely and accurately maintain our financial records, interference with our clients’ ability to contract for, or the ability of talent to complete, projects on our work marketplace, inaccurate or delayed invoicing of clients, delay of payment

to us or talent, claims by users for losses sustained by them, or investigation and corrective action taken by regulatory agencies. In such an event, we may be required, or may choose, for customer relations or other reasons, to expend additional resources in order to help resolve the issue. Accordingly, any errors, defects, or disruptions in our work marketplace could adversely impact our brand and reputation, revenue, and operating results.

Our ability to attract and retain users is dependent in part on ease of use and reliability of our work marketplace and the quality of our support, and any failure to offer high-quality support could adversely impact our business, operating results, and financial condition.

Our ability to attract and retain users is dependent in part on the ease of use, trustworthiness, and reliability of our work marketplace, including our ability to provide high-quality support. Our users depend on our support organization to enforce our terms of service against bad actors, to resolve any issues relating to our work marketplace, to communicate effectively about their accounts, and to assist in their use of our work marketplace, especially large enterprise clients, which expect higher levels of support. Our ability to provide effective support is largely dependent on our ability to attract, resource, and retain service providers who are both qualified to support users of our work marketplace and well versed in our work marketplace. Offering our website and user support only in English may negatively impact our relationships with our users, particularly users in non-English speaking countries. As we seek to continue to grow our international user base, our support organization will face additional challenges, including those associated with delivering support and documentation in languages other than English. Any failure to maintain high-quality support or effectively communicate with our users, or any market perception that we do not maintain high-quality support or act professionally, fairly, or effectively in our communications and actions with respect to users, could harm our reputation, adversely affect our ability to sell our work marketplace to existing and prospective users, and could adversely impact our business, operating results, and financial condition.

We rely on AWS to deliver our work marketplace to our users, and any disruption of service from AWS or material change to our arrangement with AWS could adversely affect our business.

We currently host our work marketplace, serve our users, and support our operations using Amazon Web Services, which we refer to as AWS, a provider of cloud infrastructure services. We do not have control over the operations of the facilities of AWS that we use. AWS’s facilities are vulnerable to failure, damage, or interruption from a number of causes, including from earthquakes, hurricanes, floods, fires, cybersecurity attacks, terrorist attacks, power losses, telecommunications failures, and similar events, or could be subject to break-ins, computer viruses, sabotage, intentional acts of vandalism, and other misconduct. The occurrence of any of these events, a decision to close the facilities or cease or limit providing services to us without adequate notice, or other unanticipated problems could result in interruptions to our work marketplace, including lengthy interruptions. Our work marketplace’s continuing and uninterrupted performance is critical to our success and users may become dissatisfied by any system failure that interrupts our ability to provide our work marketplace to them. We may not be able to easily switch our AWS operations to another cloud or other data center provider if there are disruptions or interference with our use of AWS, and, even if we do switch our operations, other cloud and data center providers are subject to the same risks. Sustained or repeated system failures could reduce the attractiveness of our work marketplace to users, cause users to decrease their use of or cease using our work marketplace, and adversely affect our business. Moreover, negative publicity arising from these

types of disruptions could damage our reputation and may adversely impact use of our work marketplace. We may not carry sufficient business interruption insurance to compensate us for losses that may occur as a result of any events that cause interruptions in our service and we cannot be certain that insurance will continue to be available to us on economically reasonable terms, or at all.

AWS does not have an obligation to renew its agreements with us on commercially reasonable terms, or at all. If we are unable to renew our agreements or unable to renew on commercially reasonable terms, our agreements are prematurely terminated, or we add additional infrastructure providers, we may experience costs or downtime in connection with the transfer to, or the addition of, new data center

providers. If these providers charge high costs for or increase the cost of their services, we may have to increase the fees to use our work marketplace and our operating results may be adversely impacted.

Our ability to attract and retain users is dependent in part on the quality of our support, and any failure to offer high-quality support could adversely impact our business, operating results, and financial condition.

Our ability to attract and retain users is dependent in part on the ease of use, trustworthiness, and reliability of our work marketplace, including our ability to provide high-quality support. Our users depend on our support organization to enforce our terms of service against bad actors, to resolve any issues relating to our work marketplace, to communicate effectively about their accounts, and to assist in their use of our work marketplace, especially large enterprise clients, which expect higher levels of support. Our ability to provide effective support is largely dependent on our ability to attract, resource, and retain service providers who are both qualified to support users of our work marketplace and well versed in our work marketplace. The incorporation of generative artificial intelligence into our support tools, either by us or our third-party support partners, may lead to inconsistent quality of experience as these generative artificial intelligence tools are integrated and refined. Offering our website and user support only in English may negatively impact our relationships with our users, particularly users in non-English speaking countries. As we seek to continue to grow our international user base, our support organization will face additional challenges, including those associated with delivering support and documentation in languages other than English. Any failure to maintain high-quality support or effectively communicate with our users, or any market perception that we do not maintain high-quality support or act professionally, fairly, or effectively in our communications and actions with respect to users, could harm our reputation, adversely affect our ability to sell our work marketplace to existing and prospective users, and could adversely impact our business, operating results, and financial condition.

Our user growth and engagement on mobile devices depend upon third parties maintaining open application marketplaces and effective operation with mobile operating systems, networks, and standards that we do not control.

Mobile devices are increasingly used for marketplace transactions. A significant and growing portion of our users access our work marketplace through mobile devices, including through ~~the use of~~ mobile applications. Our mobile applications rely on third parties maintaining open application store platforms, including the Apple App Store and Google Play, which make current and new applications or new versions of our mobile applications available for download and use on mobile devices. We cannot assure you that ~~the~~these platforms ~~through which we distribute our applications~~ will maintain their current structures or terms of access, ~~that such marketplaces~~ will continue to make our mobile applications or newer versions of our mobile applications available for download, or ~~that such marketplaces~~ will not charge us new or additional fees or impose other new or additional requirements, including requirements that may be costly and burdensome to meet or may adversely affect user ~~experience, to list our applications for download or offer services and offerings through our applications.~~experience. Additionally, there is no guarantee that popular mobile ~~devices~~operating systems, such as Android and iOS, will continue to support our work marketplace, that any changes to such operating systems will not degrade the functionality of or user experience on our marketplace, or that the use of mobile devices for payments or other transactions on our work marketplace will be available on commercially reasonable terms, or that mobile device users will use our work marketplace rather than competing products. We are dependent on the interoperability of our work marketplace with popular mobile operating systems that we do not control, such as Android and iOS, and any changes in such systems that degrade the functionality of or user experience on our website or applications or give preferential treatment to competitors could adversely affect the usage of our work marketplace on mobile devices. Additionally, interms. In order to deliver high-quality mobile offerings, it is important that our offerings are designed effectively and work well with a range of mobile devices, technologies, systems, networks, and standards that we do not ~~control. We~~control, and we may not be successful in developing relationships with key participants in the mobile industry or in developing offerings that operate ~~effectively with these devices, technologies, systems, networks, or standards.~~effectively. In the event that it is ~~more difficult~~inconvenient for our users to access

and use our work marketplace on their mobile devices, ~~our users find our mobile offering is not cost-effective, our users find our mobile offering does not meet their needs,~~ our competitors develop offerings and services that are perceived to operate more effectively on mobile devices, or our users choose not to access or use our work marketplace on their mobile devices or use mobile products that do not offer access to our work marketplace, our user growth, user engagement, and business could be adversely impacted.

Risks Related to Legal and Regulatory Matters

We and our users may be subject to new and existing laws and regulations, both in the United States and internationally.

We and our users are subject to a wide variety of foreign and domestic laws. Laws, regulations, and standards governing issues that may affect us, such as worker classification, employment, worker health, payments, worker confidentiality obligations and whistleblowing, intellectual property, consumer protection, taxation, privacy, and data security are often complex and subject to varying interpretations, in many cases due to their lack of specificity, and, as a result, their enforcement and application in practice may change or develop over ~~time through judicial decisions or as new guidance or interpretations are provided by regulatory and governing bodies, such as federal and state administrative agencies.~~time. Many of these laws were adopted prior to the advent of the internet, mobile, and related technologies and, as a result, do not contemplate or address the unique issues of the internet, mobile, and related technologies. ~~Other laws~~The level of regulatory scrutiny on larger companies, technology companies in general, and ~~regulations~~companies engaged in dealings with independent contractors, payments, or personal information in particular, has increased significantly recently and may ~~be adopted in response~~continue to ~~internet, mobile, and related technologies.~~increase. New and existing laws and regulations (or changes in interpretation of existing laws and regulations), including those concerning worker classification, independent contractors, employment, discrimination and harassment, payments, whistleblowing and worker confidentiality obligations, intellectual property, consumer protection, taxation, privacy, data security, artificial intelligence, automated decision-making systems, algorithms and machine learning, benefits, unionizing and collective action, arbitration agreements and class action waiver provisions, unfair competition, terms of service, website accessibility,

background checks (such as the Fair Credit Reporting Act, 15 U.S.C. § 1681), escheatment, and federal contracting may also be adopted, implemented, or interpreted to apply to us and other online services marketplaces or our ~~users.~~users, including as a result of new products or features we may introduce. Likewise, these laws affect our users, and their application, or uncertainty around their application, may affect demand for our work marketplace.

~~As a result of Russia’s invasion of Ukraine, the United States, the United Kingdom, the EU,~~ Legislators and ~~other jurisdictions~~regulatory agencies have issued broad-ranging economic sanctions. As the Russian invasion of Ukraine continues, there can be no certainty regarding whether such governments or other governments will impose additional sanctions, or other economic or military measures against Russia or Belarus. Although we have suspendedenacted, and may continue to enact, new laws, rules, and regulations that are adverse to our business ~~operations in Russia~~or the interests of our users, or they may view matters or interpret or enforce laws and ~~Belarus, and block users from all sanctioned regions, users~~regulations differently than they have in the past ~~and may~~or in ~~the future, seek~~a manner adverse to ~~circumvent our efforts to block those and other jurisdictions, and therefore we are subject to risks that we may not be in full compliance with any additional sanctions.~~

As our work marketplace’s geographic scope expands, including efforts to increase adoption by users outside the United States and extending our physical presence internationally, and as we expand or change the offerings and services offered on our work marketplace, regulatory agencies or courts may claim, or we may independently determine, that we, or our users, are subject to additional regulations or requirements, or are prohibited from conducting our business or ~~conducting business with~~the interests of our users. Such legislative or regulatory scrutiny or action may create or enhance different or conflicting obligations on us ~~in or with certain jurisdictions, either generally or with respect~~from one jurisdiction to ~~certain offerings or services, or that we are otherwise required to change our business practices.~~ another.

If we determine additional legal requirements apply to our business, we may expend resources to comply or obtain licenses to come into compliance with such requirements, and such efforts may be a distraction to the business or require adverse changes to the manner in which we conduct our business or our work marketplace and may themselves cause regulatory agencies to scrutinize our business, including past practices. It is also possible that certain provisions in agreements with our users or service providers, or between talent and clients, or the fees we charge, may be found to be unenforceable or not compliant with applicable law. Any failure by us to comply with applicable laws could adversely affect our business.

The ~~level of~~ regulatory ~~scrutiny on larger companies, technology companies~~landscape regarding contractor classification is rapidly changing and changes in ~~general,~~these laws could adversely affect demand for our services and ~~companies engaged in dealings with independent contractors, payments, or personal information in particular, has increased significantly recently~~work marketplace and ~~may continue to increase. Legislators have enacted, and may continue to enact, new laws or regulatory agencies may promulgate new rules or regulations that are adverse to~~adversely affect our business or the interests of our users, or they may view matters or interpret or enforce laws and regulations differently than they have in the past or in a manner adverse to our business or the interests of our users. Such legislative or regulatory scrutiny or action may create or enhance different or conflicting obligations on us from one jurisdiction to another.

~~New approaches to policy-making and legislation may also produce unintended harms to our business, which may impact our ability to operate our business in the manner in which we are accustomed.~~business. In ~~particular,~~addition, there has been increased focus on technology, artificial intelligence, and worker classification and independent contractor regulations. For example, the focus on worker classification led in part to the adoption of legislation in California, and it is possible that other jurisdictions will implement similar laws and regulations, as discussed in the risk factor titled “There may be adverse tax, legal, and other consequences if the contractor classification or employment status of talent that use our work marketplace is challenged.~~” These types of laws and regulations may have a far-reaching impact, including on~~

Clients are generally responsible for properly classifying the ~~independent professionals that use~~talent they engage through our work marketplace ~~and their clients. Any~~under our terms of ~~these regulations could negatively impact our~~service. Some clients opt to classify talent as employees for certain work, while talent in many other cases are classified as independent contractors.

We offer an optional service to users ~~including perceptions regarding their use~~ of our ~~work marketplace, or have a material adverse effect on the demand for talent on our work marketplace or on the manner in~~Upwork Enterprise offering and other premium offerings, through which we ~~are able to operate our work marketplace.~~

~~As we look to expand our international footprint over time, we may become obligated to comply with additional laws and regulations~~help classify talent as employees of ~~the countries~~third-party staffing providers or markets in which we operate or have users or employees. We may be harmed if we are found to be subject to new or existing laws and regulations or if those laws are interpreted and applied to us in a manner that harms our business or is inconsistent with the application of U.S. laws, including those concerning worker classification, independent ~~contractors, employment, payments, whistleblowing and worker confidentiality obligations, intellectual property,~~

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~~consumer protection, taxation, privacy, data security, benefits, unionizing~~contractors. For clients of these services, subject to applicable law and ~~collective action, arbitration agreements and class action waiver provisions, unfair competition,~~the terms of ~~service, website accessibility, background checks,~~our agreement with the client, we indemnify clients from misclassification risk and ~~escheatment.~~make warranties to the client, such as to compliance with applicable laws. In addition, ~~contractual provisions~~we offer a number of other premium offerings where we provide increased assistance to users to find and contract with one another, which could increase employment-related risks. Third-party staffing providers employ talent classified as employees for clients, and failure of these staffing providers to comply with all legal and tax requirements could adversely affect our business. We also use our work marketplace to find, classify, and engage talent to provide services for us and for our managed services offering.

There is significant uncertainty in the worker classification regulatory landscape and the application of worker classification laws, which are regularly subject to further regulation, amendment, or re-interpretation, and consequently there is risk to us and to users, both talent and clients, that are designed to protect and mitigate against risks, including terms of service, services agreements, arbitration and class action waiver provisions, disclaimers of warranties, limitations of liabilities, releases of claims, and indemnification provisions,independent contractors could be deemed ~~unenforceable~~to be misclassified under applicable law, including as a result of changes in our offerings or brand positioning that we may introduce. Compliance with any new legislation or regulations may be costly and difficult, or compliance in a commercially reasonable manner may not be possible. Additionally, the tests governing whether a service provider is an independent contractor or an employee are typically highly fact sensitive and vary by governing law. Laws and regulations that govern the status and misclassification of independent contractors are also subject to change as well as to divergent interpretations by various authorities, which can create uncertainty and unpredictability. For example, in California, Assembly Bill 5, which we refer to as AB 5, went into effect on January 1, 2020 and has the ~~application~~stated purpose of ~~these~~codifying the 2018 state supreme court decision in Dynamex Operations West, Inc. v. Superior Court of Los Angeles. Together, they retroactively change the standard in California for determining worker classification and are widely viewed as expanding the scope of the definition of “employee” for most purposes under California law. Since the enactment of AB 5, and subsequent amendments and challenges (including California’s Proposition 22) to the law, there is little guidance from the courts or the regulatory authorities charged with its enforcement and there remains a degree of uncertainty regarding its application. Further, in October 2022, the U.S. Department of Labor published a Notice of Proposed Rulemaking regarding the classification of workers as independent contractors or employees, which if passed could expand the scope of the definition of “employee” under federal law. Likewise, jurisdictions outside the United States, such as the United Kingdom and the European Union, which we refer to as the EU, through its work on the Platform Workers Directive and other legislative and regulatory instruments, may change their definition of “employment” to include arrangements currently viewed as independent. Even if any new rules, laws or regulations do not directly impact our business, public perception may result in confusion about the standards to be applied when making an employment determination and cause customers to explore alternative arrangements to meet their talent needs.

We have in the past been, and may in the future be, subject to administrative inquiries and audits concerning the taxation and classification of our workers and the users of our work marketplace. Certain claims may not be covered by our insurance, and we cannot be certain that any insurance coverage that we have or may obtain will extend to or be adequate for liabilities actually incurred or that insurance will continue to be available to us on economically reasonable terms, or at all. A misclassification determination, allegation, claim, or audit creates potential exposure for users and for us, including: reputational harm and monetary exposure arising from or relating to failure to withhold and remit taxes, unpaid wages, and wage and hour laws and requirements (such as those pertaining to minimum wage and overtime); claims for employee benefits, social security contributions, and workers’ compensation and unemployment insurance; claims of discrimination, harassment, and retaliation under civil rights laws; claims under laws pertaining to unionizing, collective bargaining, and other concerted activity; and other claims, charges, or other proceedings under laws and regulations applicable to employers and employees, including risks relating to allegations of joint employer liability. Such claims could result in monetary damages (including wage-based damages or restitution, compensatory damages, liquidated damages, and punitive damages), interest, fines, penalties, costs, fees (including attorneys’ fees), criminal and other liability, assessment, injunctive relief, or settlement. These claims may also become more frequent as our brand awareness increases and as we launch new products or features. Such a claim, allegation, or adverse determination, including with respect to the talent that provide services to us, or the requirement for us to indemnify a client, could also harm our brand and reputation, which could adversely

impact our business. While these risks are mitigated, in part, by ~~a court, arbitrator,~~our contractual rights of indemnification against third-party claims, any limitations or ~~other decision-making body. If~~obligations that we ~~are unable~~include in our contracts with clients to ~~comply with these laws~~limit our exposure to claims could be determined to be unenforceable, could be costly to enforce or ineffective, or may otherwise prove inadequate.

In addition, any developments or changes in the regulatory environment impacting worker classification and ~~regulations or manage~~independent contractors may reduce the complexity of global operations and supporting an international user base successfully or in a cost-effective manner, or if these laws and regulations are found to apply to our users or cause a decline in demand for ~~talent services,~~independent contractors more generally in one or more jurisdictions and have an adverse effect on our business, operating results, and financial ~~condition could be adversely affected.~~condition.

Having an international community of users and engaging talent internationally exposes us to risks that could have an adverse effect on our business, operating results, and financial condition, and these risks could increase as we seek to expand our international footprint.

Even though we currently have a limited physical presence outside of the United States, ~~our users have a global footprint that subjects us to the risks of being found to do business internationally. We~~we have users of our work marketplace located in over 180 countries, including some markets where we have limited experience, where challenges can be significantly different from those we have faced in more developed markets, and where business practices may create greater internal control risks. Further, certain skills and services are offered by talent concentrated in countries with higher risks of instability and geopolitical uncertainty. For example, approximately 25% of client spend from our web, mobile, and software development category in 2021 was derived from work where either the talent or the client was located in Ukraine, Russia, or Belarus. ~~Russia’s invasion of~~The war in Ukraine has interfered and may continue to interfere with talent’s ability to access our work marketplace and for us to support users in such countries and the surrounding region. In particular, in response to the ongoing war in Ukraine, we ~~suspended~~decided in March 2022 to suspend business operations in Russia and Belarus, which means that users in each of those countries are prohibited from using our work marketplace for the duration of the suspension. In addition, we engage talent located in many countries to provide services for our managed services offering and to us for internal projects. As a result of our decision to suspend business operations in Russia and Belarus, we also suspended our engagements with talent in those countries that we engage on our work marketplace to perform services for us.

Because our website is generally accessible by users worldwide, we have received in the past, and may continue to receive, notices from jurisdictions claiming that we or our users are required to comply with their laws. Laws outside of the United States regulating the internet, payments, escrow, data protection, data residency, privacy, taxation, terms of service, website accessibility, consumer protection, intellectual property ownership, services intermediaries, payment intermediaries, money laundering, labor and employment, wage and hour, worker classification, worker health, background checks, and recruiting and staffing companies, among others, which could be interpreted to apply to us, are often less favorable to us than those in the United States, giving greater rights to competitors, users, and other third parties. Compliance with international laws and regulations may be more costly than expected, may require us to change our business practices or restrict or modify our offerings or obtain certain licenses, and such changes or licensure may not be possible on a reasonable timeline or at all, and the imposition of any such laws or regulations on us, our users, or third parties that we or our users utilize to provide or use our services, may adversely impact our revenue and business. In addition, we may be subject to multiple overlapping legal or regulatory regimes that impose conflicting requirements, including relating to data protection and privacy, which could lead to additional compliance costs and enhanced legal risks. Moreover, all of these risks will be exacerbated as we expand our operations internationally, including extending our physical presence and registering to do business outside the United States or investing in localization efforts.

~~Risks~~Additional risks inherent in conducting business with an international user base, engaging talent globally, localizing our work marketplace, and expanding our operations internationally include, but are not limited to:

•being deemed to conduct business or have operations in the jurisdictions where users, including talent that provide services to us, or employees are resident and being subject to their laws and regulatory requirements;

•~~new, changed, or conflicting regulatory requirements;~~

•varying worker classification standards, regulations, and approaches to enforcement and requirements and expectations of employment;

•difficulties in, and costs of, establishing local brand recognition and staffing, managing, and operating international operations or support functions;

•compliance with U.S. and foreign laws designed to combat money laundering and the financing of terrorist activities;

•the imposition of taxes on transactions between us and our users or among our users, or the imposition of liability on us for the failure to collect and remit taxes owed by our users;

•compliance with U.S. and foreign laws and regulations regarding privacy, data protection, information security, and the collection, storing, retention, sharing, use, processing, transfer, disclosure, and protection of personal information and other content;

•the cost and burden of complying with a wide variety of laws that may be deemed to apply to us, including those relating to labor and employment matters (including but not limited to requirements with respect to works councils or similar labor organizations, worker classification, and taxation on income or earnings, including the obligation to withhold and remit taxes), payments and the handling, storing, or moving of money, consumer and data protection, privacy, network security, encryption, data residency, and taxes, as well as securing expertise in local law and related practices;

•tariffs, export and import restrictions, restrictions on foreign investments, sanctions, changes to existing trade arrangements between various countries, and other trade barriers or protection measures, including those affecting certain countries with higher risks of instability and geopolitical uncertainty, such as Russia and Ukraine;

•geopolitical instability and security risks, such as armed conflict and civil or military unrest, political instability, human rights concerns, and terrorist activity in countries where we have users, such as the ongoing ~~Russian~~ war ~~against Ukraine;~~in Ukraine, and retaliatory actions that governments may take in response;

•costs of localizing services and business practices, including adding the ability for clients to pay in local currencies or modifying our platform to offer our website in local ~~languages;~~languages and the related lack of acceptance of localized services or of services generally because they are not localized;

•changes to laws, regulations, or central bank rules impacting us or our partners that may make payments for services exports more costly, difficult, or impossible to process, or that may reduce the availability of tools like digital wallets and related payment services in important global markets;

•~~retaliatory actions by~~compliance with U.S. and foreign ~~governments intended~~data protection and privacy laws that impose complex data handling obligations, including honoring users’ jurisdiction-specific rights related to ~~disrupt business like ours in the United States as a result of new or increased sanctions or export controls;~~their personal data;

•~~macroeconomic~~contractual provisions that are designed to protect and ~~political conditions,~~mitigate against risks, including ~~in certain~~terms of service, services agreements, arbitration and class action waiver provisions, disclaimers of warranties, limitations of liabilities, releases of claims, and indemnification provisions, could be deemed unenforceable by a foreign ~~jurisdictions such as the evolving relations between the United States and China;~~court, arbitrator, or other decision-making body;

•economic weakness or currency-related challenges or crises;

•fluctuations in foreign currency exchange rates, including losses borne by our customers that cause them to find our work marketplace to be less desirable or to hold us responsible for such losses;

•regional or global public health crises, such as the COVID-19 pandemic;

•~~difficulties in, and costs of, establishing local brand recognition and staffing, managing, and operating international operations or support functions;~~

•~~lack of acceptance of localized services or of services generally because they are not localized;~~

•private, corporate or state-sponsored espionage, ransomware, or cyberterrorism;

•~~weaker intellectual property protection;~~ and

•organizing or similar activity by workers, local unions, works councils, or other labor organizations in the U.S. or ~~elsewhere; and~~

•~~our ability to adapt to business practices and client requirements in different cultures.~~elsewhere.

The risks described above may also make it costly or difficult for us to expand our operations internationally. Analysis of, and compliance with, foreign laws and regulations may substantially increase our cost of doing business. We may be unable to keep current with changes in laws and regulations as they develop. Although we have implemented policies and procedures designed to analyze whether these laws apply and, if applicable, support compliance with these laws and regulations, there can be no assurance that we will always maintain compliance, that our interpretations are or will remain correct, or that all of our employees, contractors, partners, users, and agents will comply. Any violations could result in enforcement actions or other proceedings, fines, civil and criminal penalties, damages, interest, costs and fees (including ~~but not limited to~~ legal fees), injunctions, loss of intellectual property rights, or reputational harm. If we are unable to comply with these laws and regulations or manage the complexity of global operations and

support an international user base successfully and in a cost-effective manner, our business, operating results, and financial condition could be adversely affected.

~~There may be adverse tax, legal, and other consequences if the contractor classification or employment status of talent that use our work marketplace is challenged.~~

Clients are generally responsible for properly classifying the talent they engage through our work marketplace under our terms of service. Some clients opt to classify talent as employees for certain work, while talent in many other cases are classified as independent contractors.

We offer an optional service to users of our Upwork Enterprise offering and other premium offerings, through which we help classify talent as employees of third-party staffing providers or independent contractors. For clients of these services, subject to applicable law and the terms of our agreement with the client, we indemnify clients from misclassification risk and make warranties to the client, such as to compliance with applicable laws. In addition, we offer a number of other premium offerings where we provide increased assistance to users to find and contract with one another, which could increase employment-related risks. Third-party staffing providers employ talent classified as employees for clients, and failure of these staffing providers to comply with all legal and tax requirements could adversely affect our business. Moreover, material business changes by one or more of our third-party staffing providers could negatively impact our business and financial results, including increased costs for clients or us, a reduced profit margin, a diminished user experience, or the inability to offer the staffing provider services in one or more jurisdictions. We also use our work marketplace to find, classify, and engage talent to provide services for us and for our managed services offering. In general, any time a court or administrative agency determines that we or our clients that use our work marketplace have misclassified talent as an independent contractor, we or our users could incur tax and other liabilities for failing to properly withhold or pay taxes on the talent’s compensation, for failing to properly compensate the talent, including benefits and stock compensation, as well as potential wage and hour penalties and other liabilities depending on the circumstances and jurisdiction. We have in the past been, and may in the future be, subject to administrative inquiries and audits concerning the taxation and classification of our workers and the users of our work marketplace. Certain claims may not be covered by our insurance, and we cannot be certain that any insurance coverage that we have or may obtain will extend to or be adequate for liabilities actually incurred or that insurance will continue to be available to us on economically reasonable terms, or at all.

There is often uncertainty in the application of worker classification laws, which are regularly subject to regulation, amendment, or re-interpretation, and consequently there is risk to us and to users, both talent and clients, that independent contractors could be deemed to be misclassified under applicable law. The tests governing whether a service provider is an independent contractor or an employee are typically highly fact sensitive and vary by governing law. Laws and regulations that govern the status and misclassification of independent contractors are also subject to change as well as to divergent interpretations by various authorities, which can create uncertainty and unpredictability. For example, in California, Assembly Bill 5, which we refer to as AB 5, went into effect on January 1, 2020 and has the stated purpose of codifying the 2018 state supreme court decision in ~~Dynamex Operations West, Inc. v. Superior Court of Los Angeles~~. Together, they retroactively change the standard in California for determining worker classification and are widely viewed as expanding the scope of the definition of “employee” for most purposes under California law. Since the enactment of AB 5, and subsequent amendments and challenges (including California’s Proposition 22) to the law, there is little guidance from the courts or the regulatory authorities charged with its enforcement and there remains a degree of uncertainty regarding its application.

A misclassification determination, allegation, claim, or audit creates potential exposure for users and for us, including but not limited to: reputational harm and monetary exposure arising from or relating to failure to withhold and remit taxes, unpaid wages, and wage and hour laws and requirements (such as those pertaining to minimum wage and overtime); claims for employee benefits, social security contributions, and workers’ compensation and unemployment insurance; claims of discrimination, harassment, and retaliation under civil rights laws; claims under laws pertaining to unionizing, collective bargaining, and other concerted activity; and other claims, charges, or other proceedings under laws and regulations applicable to employers and employees, including risks relating to allegations of joint employer liability. Such claims could result in monetary damages (including but not limited to wage-based damages or restitution, compensatory damages, liquidated damages, and punitive damages), interest, fines, penalties, costs, fees (including but not limited to attorneys’ fees), criminal and other liability, assessment, injunctive relief, or settlement. For example, particularly around the onset of the COVID-19 pandemic, these types of claims were more frequent in light of then-deteriorating macroeconomic conditions, more prone to agency error in light of overwhelmed agencies, more commonly submitted on a fraudulent basis, and more difficult to successfully oppose or appeal due to COVID-19 related delays, and such events may increase in frequency again if similar circumstances recur. These claims may also become more frequent as our brand awareness increases. Such a claim, allegation, or adverse determination, including but not limited to with respect to the talent that provide services to us, or the requirement for us to indemnify a client, could also harm our brand and reputation, which could adversely impact our business. While these risks are mitigated, in part, by our contractual rights of indemnification against third-party claims, any limitations or obligations that we include in our contracts with clients to limit our exposure to claims could be determined to be unenforceable, could be costly to enforce or ineffective, or may otherwise prove inadequate.

The regulatory landscape regarding contractor classification is rapidly changing, and changes in these laws could adversely affect demand for our services and work marketplace and adversely affect our business.

Worker classification and independent contractor issues, including AB 5, have been the subject of widespread debate both in the United States and abroad. It is possible that other jurisdictions, including the U.S. federal government, U.S. states, such as New York, Washington, and Illinois, and jurisdictions outside the United States, such as the United Kingdom and the EU through its work on the Platform Workers Directive and other legislative and regulatory instruments, may change their definition of “employment” to include arrangements currently viewed as independent. The U.S. Department of Labor recently published a Notice of Proposed Rulemaking regarding the classification of workers as independent contractors or employees. The proposal is widely viewed as expanding the scope of the definition of employee under federal law. It is uncertain how this rule, if enacted as proposed, would impact our business, if at all. However, public perception may result in confusion about the standards to be applied when making an employment determination and cause customers to explore alternative

arrangements to meet their talent needs. Additionally, changes to laws and regulation may be subject to challenge in court (e.g. AB 5, which had a retroactive effect, and California’s Proposition 22, which was ruled unconstitutional). Likewise, the EU, the United Kingdom, and other jurisdictions are exploring changes to worker classification through a variety of legal instruments, such as the Digital Services Act and Digital Markets Act in the EU. These new and changing laws could alter the legislative and regulatory landscape regarding how governments may choose to regulate independent contractors broadly and in specific sectors, and may have unintended consequences. These changes may affect how our users run their businesses. As a result, there is significant uncertainty regarding the worker classification regulatory landscape and what it will look like in future years, and compliance with any new legislation or regulations may be costly and difficult or they may be impossible to comply with in a commercially reasonable manner. In addition, any developments or changes in the regulatory environment impacting worker classification and independent contractors may reduce the demand for independent contractors more generally in one or more jurisdictions and have an adverse effect on our business, operating results, and financial condition.

Changes in laws or regulations relating to privacy or the protection, collection, storage, processing, transfer, or use of personal information, or any actual or perceived failure by us to comply with such laws and regulations or our privacy policies, could adversely affect our business.

We receive, collect, store, process, transfer, and use personal information and other user data. There are numerous federal, state, local, and international laws and regulations regarding privacy, data protection, information security, and the collection, storing, sharing, use, processing, transfer, disclosure, and protection of personal information and other data. The scope of these laws and regulations is changing, subject to differing interpretations, and may be inconsistent among states and countries, or conflict with other laws and regulations. We are also subject to the terms of our privacy policies and legal and contractual obligations to third parties related to privacy, data protection, and information security. The regulatory framework for privacy and data protection worldwide is, and is likely to remain for the foreseeable future, uncertain and complex, and it is possible that these or other actual or alleged obligations may be interpreted and applied in a manner that we do not anticipate or that is inconsistent from one jurisdiction to another and may conflict with other rules or our practices. ~~Further, any~~In addition, public and regulatory scrutiny of and complaints about technology companies in general regarding their data handling or data protection practices has increased. Any significant change to applicable laws, regulations, or industry practices regarding the collection, use, retention, security, sharing, or disclosure of the data of our users, employees, contractors, or others, or their interpretation or enforcement, or any changes regarding the manner in which the express or implied consent of users for the collection, use, retention, sharing, or disclosure of such data must be obtained, could increase our costs and require us to modify our services and features, possibly in a material manner, which we may be unable to complete in a cost-effective manner, or at all, and may limit our ability to store and process user data or develop new services and features.

We also expect that there will continue to be new laws, regulations, and industry standards concerning privacy, data protection, automated processing, and information security that are proposed and enacted in various jurisdictions. For example, Europe’s General Data Protection Regulation, which we refer to as the GDPR, ~~and~~ the UK General Data Protection Regulation (which implements the GDPR into UK law), and Europe’s Digital Services Act impose stringent data protection and data handling compliance requirements and provide for significant penalties for noncompliance. Additionally, there is an increased focus on automated processing and processing via artificial intelligence that may lead to increased regulatory restrictions that could have an impact on portions of our platform’s functionality. The CCPA, in conjunction with its California Privacy Rights Act amendment, requires, among other things, covered companies to provide certain disclosures to California consumers and affords such consumers certain rights, including the right to opt-out of certain sales of personal data. The CCPA also provides for civil penalties for violations as well as a private right of action for data breaches that may increase data breach litigation. Further, the California Privacy Rights Act, which was passed in November 2020 and will be fully effective in January 2023, significantly modifies the CCPA. These modifications will require us to incur additional costs and expenses in our effort to comply. Virginia, Colorado, Utah, Connecticut, Iowa, and ~~Connecticut recently~~Washington have enacted similar or other data ~~privacy~~protection legislation that have or will ~~take~~go into staggered effect in ~~2023,~~the near future, and several other states and countries are considering expanding or passing privacy laws in the near term. The enactment of more restrictive laws, rules, regulations, or future enforcement

actions or investigations could impact us through increased costs or restrictions on our business, and noncompliance could result in regulatory penalties and significant legal liability. Furthermore, the costs of compliance with, and other burdens imposed by, the laws, regulations, and policies that are applicable to the businesses of our users may limit the adoption and use of, and reduce the overall demand for, our work marketplace.

Additionally, if third parties we work with violate applicable laws, regulations, or agreements, such violations may put the data of our users, employees, contractors, and others at risk, could result in governmental investigations or enforcement actions, fines, litigation, claims, or public statements against us by consumer advocacy groups or others, and could result in significant liability, cause our users to lose trust in us, and otherwise have an adverse effect on our reputation and business. Further, public scrutiny of or complaints about technology companies or their data handling or data protection practices, even if unrelated to our business, industry, or operations, may lead to increased scrutiny of technology companies, including us, and may cause government agencies to enact additional regulatory requirements, or to modify their enforcement or investigation activities, which may disrupt the conduct of our business, increase our liability, increase our costs and risks, and adversely affect our business.

We may be subject to escrow, payment or money services, and money transmitter regulations that may adversely affect our business.

Our subsidiary, Upwork Escrow, is licensed as an internet escrow agent under California’s Escrow Law and is subject to regulations applicable to internet escrow agents promulgated by the DFPI. While we have received two inquiries, each prior to 2014 and under outdated legal frameworks, from regulatory authorities inquiring whether we are engaging in payment activities, these inquiries were resolved in our favor and did not require us to obtain a license in the applicable jurisdiction.

Although we are a licensed internet escrow agent and we believe that our operations comply with existing U.S. federal, state, and international laws and regulatory requirements related to escrow, money transmission, and the handling or moving of money, the laws or regulations may change, interpretations of existing laws and regulations may also change, and our operations and offerings may change resulting in new or different regulatory requirements being applicable to or preferable for our business. As a result, we could be required, or choose, to become licensed as an escrow agent or a money transmitter (or other similar licensee) in other U.S. states or other jurisdictions or as a money services business under federal laws and regulations or similar licenses under the laws and regulations of other jurisdictions. It is also possible that we could become subject to regulatory enforcement or other proceedings in ~~those~~ states or other jurisdictions with escrow, money transmission, electronic money, or other similar statutes or regulatory requirements related to the handling, storing, or moving of money, and such risk may increase if we are required or choose to pursue additional or different licenses, which could in turn have a significant impact on our business, even if we voluntarily sought the licenses or were to ultimately prevail in such proceedings. For example, we received two inquiries, each prior to 2014 and under outdated legal frameworks, from regulatory authorities inquiring whether we are engaging in payment activities; these inquiries were resolved in our favor and did not require us to obtain a license in the applicable jurisdiction. We may also be required, or choose, to become licensed as a payment institution (or obtain a similar license) under the European Payment Services Directive or other international laws and regulations or may choose to obtain such a license even if not required or in order to support new products or services. Any developments or inconsistencies in the requirements, interpretations, or applicability of the laws or regulations related to escrow, money transmission, or the handling, storing, or moving of money; material changes to the mandate, purview or regulatory approach at the DFPI; or increased scrutiny of our business may lead to additional compliance costs and administrative overhead. Moreover, to the extent that holding or pursuing escrow, money transmitter, or similar licenses involves complying with other regulatory frameworks, such as GDPR or CCPA, we may experience increased likelihood and impact with respect to ordinary enforcement or other proceedings related to such other laws or regulations.

The application of laws and regulations related to escrow, money transmission, and the handling or moving of money is subject to significant complexity and uncertainty, particularly as those laws relate to new and evolving business models. If we fail to comply with one or more escrow or money transmitter or other similar statutes or regulatory requirements related to the handling or moving of money in any U.S. state or other jurisdiction, we may be subject to the imposition of fines or restrictions on our business, our ability to offer some or all of our services in the relevant jurisdiction may be limited or suspended, and we may be subject to civil or criminal liability and our business, operating results, financial condition, reputation, and brand could be adversely affected.

Failure to comply with anti-corruption, anti-money laundering, and sanctions laws, and similar laws, could subject us to penalties and other adverse consequences.

We have voluntarily implemented an anti-money laundering compliance program designed to address the risk of our work marketplace being used to facilitate money laundering, terrorist financing, or other illegal activity. ~~Our~~However, our program may not be sufficient to prevent our work marketplace from being used to improperly move money or may be found not to satisfy the expectations of our partners or regulators. In addition, if we or a regulator determines that we are required to comply with the Bank Secrecy Act, ~~(BSA),~~ 31 U.S.C. § 5311, or similar laws outside of the United States, we may be required to enhance or alter our anti-money laundering compliance program. We also have policies, procedures, and technology designed to allow us to comply with U.S. economic sanctions laws and prevent our work marketplace from being used to facilitate business in countries, regions, or with persons or entities included on designated lists promulgated by the U.S. Department of the Treasury’s Office of Foreign Assets Control, which we refer to as OFAC, and equivalent foreign authorities. Our efforts to comply with OFAC regulations may not be effective, including in preventing users from using our services within the OFAC-sanctioned countries and

regions, our partners or regulators may determine they are insufficient, or we may be required to comply with new sanctions laws and regulations, which may require us to further revise or expand our compliance program. For example, as a result of ~~Russia’s invasion of~~the war in Ukraine, the United States, the United Kingdom, the EU, and other jurisdictions have issued and are continuing to issue broad-ranging economic sanctions. The result of such sanctions has negatively affected and may continue to affect our users and business. Additionally, any additional sanctions by the United States and the EU could include blocking sanctions targeting Russia and the enforcement of secondary sanctions against banks in China, India, or other markets that have continued to transact with Russian entities, which may disrupt our ability to transact with entities located in those countries. Given the technical limitations in developing controls to prevent, among other things, the ability of users to publish on our work marketplace false or deliberately misleading information or to develop sanctions-evasion methods, it is possible that we may inadvertently and without our knowledge provide services to individuals or entities that have been designated by OFAC or are located in a country subject to an embargo by the United States that may not be in compliance with the economic sanctions regulations administered by OFAC.

Consequences for failing to comply with applicable anti-money laundering and sanctions laws and regulations, even unintentional violations, could include fines, criminal and civil lawsuits, forfeiture of significant assets, or other enforcement actions. We could also be required to make costly and burdensome changes to our business practices or compliance programs as a result of regulatory scrutiny, voluntary changes we may make to our business strategy, or the expansion of our operations internationally, including expanding our presence outside the United States. In addition, any perceived or actual breach of compliance by us, our users, or payment partners with respect to applicable laws, rules, and regulations could have a significant impact on our reputation and could cause us to lose existing users, prevent us from obtaining new users, cause other payment partners to terminate or not renew their agreements with us, negatively impact investor sentiment about our company, require us to expend significant funds to remedy problems caused by violations and to avert further violations, and expose us to legal risk and potential liability, all of which may adversely affect our business, operating results, and financial condition and may cause the price of our common stock to decline.

~~For example, our~~Our and other freelancing platforms and websites have been the subject of additional scrutiny and press attention relating to North Korea. A U.S. Department of State advisory issued in July 2018 stated that “there are cases where North Korean companies exploit the anonymity provided by freelancing websites to sell their IT services to unwitting buyers.” More recently, in May 2022, the U.S. Department of State, U.S. Department of Treasury, and the Federal Bureau of Investigation issued guidance on efforts by North Korean nationals to secure freelance engagements as remote IT workers by posing as non-North Korean nationals. Additionally, press reports have stated that North Korean operatives have used various social media applications and freelancing websites, including ours. ~~Accordingly, although~~Although we have controls in place to detect and prevent such OFAC violations and our systems show no transactions with persons in North Korea, nor in any other OFAC-sanctioned jurisdictions, we may face higher levels of scrutiny by users, partners, and regulators due to the publishing of this advisory and those or similar press reports.

We are also subject to the U.S. Foreign Corrupt Practices Act, which we refer to as the FCPA, the U.S. domestic bribery statute contained in 18 U.S.C. § 201, the U.S. Travel Act, and the UK Bribery Act 2010, and may be subject to other anti-bribery laws in countries in which we conduct activities or have users.

We face significant risks if we fail to comply with the FCPA and other anti-corruption laws. In many foreign countries, particularly in countries with developing economies, it may be a local custom that businesses engage in practices that are prohibited by the FCPA or other applicable laws and regulations. We may have direct or indirect interactions with officials and employees of government agencies or state-owned or affiliated entities, and we may be held liable for the corrupt or other illegal activities of these third-party intermediaries, our employees, representatives, contractors, partners, and agents, even if we prohibit or do not explicitly authorize such activities. We have implemented an anti-corruption compliance policy, but we cannot ensure that all of our employees, users, and agents, as well as those contractors to which we outsource certain of our business operations, will not take actions in violation of our policies or agreements and applicable law, for which we may be ultimately held responsible.

Any violation by us, our users or payment partners of OFAC regulations, the FCPA, other applicable anti-corruption laws, or other anti-bribery, anti-money laundering, or sanctions laws, could result in investigations and actions by federal or state attorneys general or foreign regulators, loss of export privileges, severe criminal or civil fines and penalties or other sanctions, forfeiture of significant assets, whistleblower complaints, termination of agreements by payment partners, reputational harm, and adverse media coverage, which could have an adverse effect on our reputation, business, operating results, and prospects. In addition, responding to any enforcement action may result in a significant diversion of management’s attention and resources and significant defense costs and other professional fees. We could also be required to make costly and burdensome changes to our business practices or compliance programs as a result of regulatory scrutiny, voluntary changes we may make to our business strategy, or the expansion of our operations internationally, including expanding our presence outside the United States. Further, even if we maintain proper controls and remain in compliance with applicable anti-corruption, anti-money laundering, and sanctions laws or regulations, should any of our competitors not implement sufficient controls and be found to have violated such laws or regulations, user perception of

online freelance marketplaces in general may decrease and our business, brand, and reputation may be adversely affected.

We may be required to comply with governmental export control laws and regulations. Our failure to comply with these laws and regulations could have an adverse effect on our business and operating results.

We may be subject to export controls and other similar regulations that prohibit the shipment or provision of certain products and services to certain countries, governments, and persons, and new export controls and similar regulations are promulgated from time to time, including the recent application of new and broad-ranging export controls enacted as a result of ~~Russia’s invasion of~~the war in Ukraine. While we take precautions to prevent aspects of our work marketplace from being exported in violation of export controls, including implementing internet protocol address blocking and obtaining and relying on licenses and exemptions, when applicable, we cannot guarantee that the precautions we take will prevent violations of export control and similar laws. If we are found to be in violation of U.S. or international export control laws, it could result in substantial fines and penalties for us and for the persons working for us. In addition, our users may be subject to export control laws that do not apply to us and we may not be able to determine the applicability of such export control laws, and any violations by them could harm our reputation and they could seek to hold us responsible for any monetary losses.

In addition, various countries regulate the import and export of certain encryption and other technology, which have been expanded in response to the ~~Russian~~ war ~~against~~in Ukraine, including imposing import and export permitting and licensing requirements, and have enacted laws that could limit our ability to distribute aspects of our work marketplace or could limit our users’ ability to access our work marketplace in those countries. Changes in our work marketplace, or future changes in export and import regulations or revocation or inapplicability of our licenses may prevent our international users from utilizing our work marketplace or, in some cases, prevent the export or import of our work marketplace to certain countries, governments, or persons altogether. Any change in export or import regulations, economic sanctions or related legislation, or change in the countries, governments, persons, or technologies targeted by such regulations, could result in decreased use of our work marketplace by existing or potential users with international operations. Any decreased use of our work marketplace or limitation on our ability to export or sell our products would likely adversely affect our business, operating results, and financial results.

We are vulnerable to intellectual property infringement claims and challenges to our intellectual property rights brought against us by third parties.

We operate in a highly competitive industry, and there has been considerable activity in our industry to develop and enforce intellectual property rights. Intellectual property infringement claims against us or our users or third-party partners could result in monetary liability or a material disruption in the conduct of our business. We cannot be certain that aspects of our work marketplace, content, and brand names do not or will not infringe valid patents, trademarks, copyrights, or other intellectual property rights held by third parties, including our competitors. Also, we are now, have in the past been, and may in the future be, subject to legal proceedings and claims relating to the intellectual property of others, including our competitors, in the ordinary course of our business. The likelihood of intellectual property-related litigation and disputes may increase ~~due~~as platforms like ours gain more prominence. In addition, the improper use of generative artificial intelligence by users of our work marketplace may lead to ~~the increased attention on our market segment due to the ongoing shift to remote work.~~additional claims of intellectual property infringement. Companies, including non-practicing entities and our competitors, have also sent us demand letters and instituted proceedings alleging that we infringe their intellectual property, seeking licensing fees, royalties and damages, and demanding that we cease certain commercial activity. We may receive such demand letters and be subject to similar proceedings in the future. Our competitors and other third parties have in the past challenged, and may in the future challenge, our registration or use of our trademarks, including “Upwork,” and other intellectual property rights, and such a challenge, even if not successful, could adversely affect our brand and business. Our competitors and others may now and in the future have significantly larger and more mature patent portfolios than we have or trademarks or other rights that pre-date and take precedence over our own. We may also be obligated to indemnify certain clients on our work marketplace or strategic partners or others in connection with such

infringement claims, or to obtain licenses from third parties or modify our work marketplace or marketing strategy, and each such obligation would require us to expend additional resources and could divert the attention of management. Some of our infringement indemnification obligations related to intellectual property are contractually capped at a very high amount or not capped at all.

Any litigation or other disputes relating to allegations of intellectual property infringement could divert management attention and resources, subject us to significant legal costs and liability for damages, invalidate our proprietary rights, or force us to do one or more of the following:

•suspend or cease conducting certain operations in some or all jurisdictions, or stop using technology that contains the allegedly infringing intellectual property;

•stop using the name “Upwork” or other trademarks in some or all jurisdictions;

•incur significant legal expenses;

•pay substantial damages or ongoing royalty payments to the party whose intellectual property rights we may be found to be infringing;

•pay substantial amounts in settlement to a party that asserts allegations of intellectual property infringement;

•prevent us from offering aspects of our work marketplace or make expensive and disruptive changes to our work marketplace or our methods of doing business; or

•attempt to obtain a license to the relevant intellectual property from third parties, which may not be available on reasonable terms or at all.

Even if intellectual property claims do not result in litigation or are resolved in our favor, these claims, and the time and resources necessary to resolve them, could divert resources and the attention of management and adversely affect our business and operating results. We expect that the occurrence of infringement claims is likely to grow as the market segment for independent talent and the clients that engage them grows. Accordingly, our exposure to damages resulting from infringement claims could increase and this could require us to expend additional financial and management resources.

Failure to protect our intellectual property could adversely affect our business.

Our success depends in large part on our proprietary technology and data. We rely on various intellectual property rights, including patents, copyrights, trademarks, and trade secrets, as well as confidentiality provisions and contractual arrangements, to protect our proprietary rights. In addition, to protect our brand, we also expend substantial resources to register and defend our trademarks and to prevent others from using the same or substantially similar marks. As the adoption of remote work becomes more prevalent and competitors enter our market segment, our exposure to unauthorized copying and use of our work marketplace, technology, intellectual property, and other proprietary information may increase. If we do not protect and enforce our intellectual property rights successfully or cost-effectively, including if we are unable to protect our trademarks and brand, our competitive position, business and brand may suffer, which would adversely impact our operating results.

Our pending and future patent or trademark applications may not be approved, or competitors or others may challenge the validity, enforceability, or scope of our patents, the registrability or validity of our trademarks, or the trade secret status of our proprietary information. If we are unsuccessful in a dispute or litigation, we may be unable to stop competitors or others from using our marks or confusingly similar marks, and we may suffer dilution, loss of reputation, genericization, or other harm to our brand. Efforts to protect and enforce our intellectual property rights, even if successful, may be costly, negatively impact our brand, negatively affect worker productivity, and be time consuming and distracting to our management. There can be no assurance that additional patents or trademarks will be issued or that any patents or trademarks that are issued will provide significant protection for our intellectual property. In addition, our patents, copyrights, trademarks, trade secrets, and other intellectual property rights may not provide us a significant competitive advantage. There is no assurance that the particular forms of intellectual property protection that we seek, including business decisions about when and where to file patents or register or renew trademarks and when and how to maintain and protect trade secrets, will be adequate to protect our business, or that common law protection will be sufficient for marks or in jurisdictions where we do not register the marks.

We may not pursue or file patent applications or apply for registration of copyrights or trademarks in the United States and foreign jurisdictions in which we have a presence with respect to our potentially patentable inventions, works of authorship, and marks and logos for a variety of reasons, including the cost of procuring or ability to procure such rights and the uncertainty involved in obtaining adequate protection from such applications and registrations. Moreover, recent amendments to, developing jurisprudence regarding, and possible changes to intellectual property laws and regulations, including U.S. and foreign patent law, may affect our ability to protect and enforce our intellectual property rights or defend against claims alleging we are infringing others’ rights. If the intellectual property rights that we develop are not sufficient to protect our proprietary technology and data, our brand, our business, financial condition and operating results could be adversely affected.

In addition, the laws of some countries do not provide the same level of protection for our intellectual property as do the laws of the United States. As our global reputation grows and we expand our international activities, our exposure to unauthorized copying and use of our work marketplace and proprietary information will likely increase. Despite our precautions, our intellectual property is vulnerable to unauthorized access through employee or third-party error or actions, theft, cybersecurity incidents, private or public economic espionage, and other security breaches and incidents. It is possible for third parties to infringe upon or misappropriate our intellectual property, to copy our work marketplace, and to

use information that we regard as proprietary to create products and services that compete with ours. Effective intellectual property protection may not be available to us in every country in which our work marketplace is available. In addition, many countries limit the enforceability of patents or other intellectual property rights against certain third parties, including government agencies or government contractors. In these countries, patents or other intellectual property rights may provide limited or no benefit. Further, certain countries impose additional conditions on the transfer of intellectual property rights from individuals to companies, which may make it more difficult for us to secure and maintain intellectual property protection in those countries. We may need to expend additional resources to defend our intellectual property rights domestically or internationally, which could be costly, time consuming, and distracting to management and could impair our business or adversely affect our domestic or international

expansion. If we cannot adequately protect and defend our intellectual property, we may not remain competitive, and our business, operating results, and financial condition may be adversely affected.

We rely on trade secrets as an important aspect of our intellectual property program and to cover much of our technology and know-how. We seek to protect our trade secrets and obtain rights in intellectual property developed by service providers through confidentiality and invention assignment or intellectual property ownership agreements with our employees, contractors, and other parties. In addition, for employees of third-party staffing providers or other contractors, the employer agrees to enter into these agreements with individual workers. We also take other measures to protect our information and data, includingparties, as well as through implementing acceptable use policies, limiting access to our information and data through technological means, and monitoring and limiting the dissemination of our information and data outside of company-owned information systems. We cannot ensure that these agreements, or all the terms thereof, will be enforceable or compliant with applicable law, or these agreements and other measures will be effective in ~~controlling access to, use of,~~protecting our trade secrets and ~~distribution of our proprietary information or in effectively securing and maintaining exclusive ownership of~~ intellectual property ~~developed by our current or former employees and contractors.~~rights. Most of our employees and all of the contractors with which we work are remote, which may make it more difficult to control use of confidential materials, increasing the risk that our source code or other confidential or trade secret information may be exposed. Further, these agreements with our employees, contractors, and other parties may not prevent other parties from independently developing technologies that are substantially equivalent or superior to our work marketplace. Any failure to protect intellectual property that we develop or our proprietary technology and data would adversely affect our business, operating results, and financial condition.

We spend significant time and resources securing and monitoring our intellectual property rights, and we may or may not be able to detect infringement by third parties. Our competitive position may be adversely impacted if our efforts to secure and protect our intellectual property are not successful, or we cannot detect infringement or enforce our intellectual property rights quickly or at all. In some circumstances, we may choose not to pursue enforcement because an infringer may have a dominant intellectual property position or for other business reasons. In addition, competitors might avoid infringement by designing around our intellectual property rights or by developing non-infringing competing technologies. We have in the past been, and may in the future be, forced to rely on litigation, opposition, and cancellation actions, and other claims and enforcement actions to protect our intellectual property, including to dispute registration, use of marks that may be confusingly similar to our own marks, or use of technologies that infringe on our intellectual property. Similar claims and other litigation may be necessary in the future to enforce and protect our intellectual property rights. Litigation brought to protect and enforce our intellectual property rights could be costly, time-consuming, and distracting to management, and could result in the impairment or loss of portions of our intellectual property. Further, our efforts to enforce our intellectual property rights may be met with: defenses; counterclaims attacking the scope, validity, and enforceability of our intellectual property rights; or counterclaims and countersuits asserting infringement by us of third-party intellectual property rights. Our failure to secure, protect, and enforce our intellectual property rights could adversely affect our brand and our business, and we could lose the right to use certain intellectual property or lose the opportunity to license our technology to others or to collect royalty payments based upon successful protection and assertion of our intellectual property against others.

Our work marketplace contains open source software components, and failure to comply with the terms of the underlying licenses could restrict our ability to market or operate our work marketplace.

Our work marketplace incorporates certain open source software. An open source license typically permits the use, modification, and distribution of software in source-code form subject to certain conditions. Some open source licenses contain conditions that any person who distributes a modification or derivative work of software that was subject to an open source license make the modified version subject to the same open source license. Distributing software that is subject to this kind of open source license can lead to a requirement that certain aspects of our work marketplace be distributed or made available in source code form. Although we do not believe that we have used open source software in a manner that might condition its use on our distribution of any portion of our work marketplace in source

code form, the interpretation of open source licenses is complex and, despite our efforts, it is possible that we may be liable for copyright infringement, breach of contract, or other claims if our use of open source software is adjudged not to comply with the applicable open source licenses.

Moreover, we cannot ensure that our processes for controlling our use of open source software in our work marketplace will be effective. If we have not complied with the terms of an applicable open source software license, we may need to seek licenses from third parties to continue offering our work marketplace and the terms on which such licenses are available may not be economically feasible, to re-engineer our work marketplace to remove or replace the open source software, to discontinue offering our

work marketplace if re-engineering could not be accomplished on a timely basis, to pay monetary damages, or to make available the source code for aspects of our proprietary technology, any of which could adversely affect our business, operating results, and financial condition.

In addition to risks related to license requirements, use of open source software can involve greater risks than those associated with use of third-party commercial software, as open source licensors generally do not provide warranties or assurances of title, performance, or non-infringement, nor do they control the origin of the software. There is typically no support available for open source software, and we cannot ensure that the authors of such open source software will implement or push updates to address security risks or will not abandon further development and maintenance. Many of the risks associated with the use of open source software, such as the lack of warranties or assurances of title or performance, cannot be eliminated, and could, if not properly addressed, negatively affect our business.

Litigation could have a material adverse impact on our operating results and financial condition.

From time to time, we are involved in litigation and make and receive demands and claims threatening possible litigation. The outcome of any litigation (including class actions and individual lawsuits or arbitration), regardless of its merits, is inherently uncertain. Regardless of the merits or ultimate outcome of any claims that have been or may be brought against us or that we may bring against others, pending or future litigation could result in a diversion of management’s attention and resources and reputational harm, and we may be required to incur significant expenses defending against these claims or pursuing claims against third parties. If we are unable to prevail in litigation, we could incur substantial liabilities. We may also determine that the most cost-effective and efficient way to resolve a dispute is to enter into a settlement agreement, and terms of any such settlement agreements are increasingly limited by legislation. Where we can make a reasonable estimate of the liability relating to pending litigation and determine that it is probable, we record a related liability. As additional information becomes available, we assess the potential liability and revise estimates as appropriate. However, because of uncertainties relating to litigation, the amount of our estimates could be wrong as determining reserves for pending litigation is a complex, fact-intensive process that is subject to judgment calls. Any adverse determination related to litigation or adverse terms contained in a settlement agreement could require us to change our technology or our business practices in costly ways, prevent us from offering certain offerings or services, require us to pay monetary damages, fines, or penalties, or require us to enter into royalty or licensing arrangements, and could adversely affect our operating results and cash flows, harm our reputation, or otherwise negatively impact our business.

If we are deemed to be an investment company under the Investment Company Act of 1940, our results of operations could be harmed.

Under Sections 3(a)(1)(A) and (C) of the Investment Company Act of 1940, as amended, which we refer to as the Investment Company Act, absent an applicable exemption, a company generally will be deemed to be an “investment company” for purposes of the Investment Company Act if (i) it is, or holds itself out as being, engaged primarily, or proposes to engage primarily, in the business of investing, reinvesting, or trading in securities or (ii) it is engaged, or proposes to engage, in the business of investing, reinvesting, owning, holding, or trading in securities and it owns or proposes to acquire investment securities having a value exceeding 40% of the value of its total assets (exclusive of U.S. government securities and cash items) on an unconsolidated basis. We do not believe that we are an “investment company,” as such term is defined in either of these sections of the Investment Company Act, including as a result of both the exemption set forth in Section 3(b)(1) of the Investment Company Act and the safe harbor set forth in Rule 3a-8 of the Investment Company Act. Section 3(b)(1) of the Investment Company Act provides that a company that would otherwise fit within the definition of an “investment company” under Section 3(a)(1)(C) of the Investment Company Act will not be required to register as an “investment company” if “it is primarily engaged, directly or through a wholly owned subsidiary or subsidiaries, in a business or businesses other than that of investing, reinvesting, owning, holding, or trading in securities.” We believe that we are and hold ourselves out as being engaged primarily in the operation of an online work marketplace, and our historical development, public representations of policy, the activity of our officers and directors, the nature of our present assets, the sources of our present income, and the public

perception of the nature of our business all support the conclusion that we are an operating company and not an investment company. Rule 3a-8 under the Investment Company Act provides a nonexclusive safe harbor from the definition of "investment company" for certain research and development companies. We are currently a research and development company and comply with the safe harbor requirements of Rule 3a-8 under the Investment Company Act. As set forth above, we currently conduct, and intend to continue to conduct, our operations so that neither we, nor any of our subsidiaries, is required to register as an “investment company” under the Investment Company Act. If we were obligated to register as an “investment company,” we would have to comply with a variety of substantive requirements under the Investment Company Act that impose, among other things, limitations on capital structure, restrictions on specified investments, prohibitions on transactions with affiliates, and compliance with reporting, record keeping, voting, proxy disclosure and other rules and regulations that would increase our operating and compliance costs, could make it impractical for us to continue our business as contemplated, and could have a material adverse effect on our business.

Risks Related to Finance, Accounting, and Tax Matters

We have a history of net losses, ~~anticipate increasing~~may increase our operating expenses in the future, and may not achieve or sustain profitability.

We have a history of incurring net ~~losses, and we expect to incur net losses for the foreseeable future.~~losses. For the ~~nine months ended September 30, 2022 and~~ years ended December 31, ~~2021~~2022 and ~~2020,~~2021, we incurred net losses of ~~$73.4 million, $56.2~~$89.9 million and ~~$22.9~~$56.2 million, respectively. As of ~~September 30, 2022,~~March 31, 2023, we had an accumulated deficit of ~~$324.4~~$323.8 million. We have made, and expect to continue to make in the future, significant expenditures related to the development and expansion of our business, including: investing in marketing programs and activities, such as brand promotion efforts, including those designed to reach new and existing clients seeking to engage remote talent in light of the ongoing shift toward remote work; expanding our sales force; enhancing our Upwork Enterprise and other premium offerings; expanding our

services and features; expanding our international user base; localizing our offerings in select locations; broadening and deepening the categories on our work marketplace; promoting client engagement of the talent that typically optimize to deliver larger projects, including through our Upwork Payroll offering; investing in marketing programs and activities, such as brand promotion efforts, including those designed to reach new and existing clients; enhancing our mobile product ~~offering and~~offering; expanding our ~~U.S.-to-U.S. domestic marketplace offering;~~sales force; and in connection with legal, accounting, and other administrative expenses related to operating as a public company. For example, beginning in the fourth quarter of 2021, we increased our investment in brand marketing and to a lesser extent, our investment in sales by expanding our sales team, and we expect to continue these increased investments in the fourth quarter of 2022. These and other efforts may prove more expensive than we currently anticipate, and we may not succeed in increasing our revenue sufficiently, or at all, to offset these higher expenses. While our GSV and revenue ~~has~~have grown in recent years, we may not be able to sustain the same level of growth in future periods, or at all. For example, inGSV remained flat at $1.0 billion during the ~~third quarter of 2022, we experienced a deceleration in year-over-year growth of revenue,~~three months ended March 31, 2023, as compared to the ~~second quarter of~~same period in 2022. We may continue to experience a similar deceleration or decline in GSV or revenue growth if the current challenging macroeconomic conditions worsen or as the impact of the COVID-19 pandemic subsides and ~~users return more frequently~~companies bring workers back to physical ~~offices or as the current macroeconomic conditions worsen.~~offices. If our revenue declines or fails to grow at a rate faster than increases in our operating expenses, we will not be able to achieve and maintain profitability in future periods and the trading price of our common stock could decline. As a result, we may continue to generate losses. We cannot ensure that we will achieve profitability in the future or that, if we do become profitable, we will be able to sustain profitability.

Our operating results and performance metrics may fluctuate from period to period, which makes our future results difficult to predict.

Our operating results and performance metrics have fluctuated recently, as they have in the past, and will likely continue to fluctuate in the future, particularly during the current macroeconomic uncertainty and rising interest rates and inflation. As a result, you should not rely upon our past operating results and performance metrics as indicators of future performance. You should take into account the risks, difficulties, and uncertainties frequently encountered by companies in highly competitive and rapidly evolving markets. Our operating results and performance metrics in any given period can be influenced by numerous factors, many of which are unpredictable or are outside of our control, including:

•uncertainty regarding macroeconomic conditions and demand for our work marketplace as the COVID-19 pandemic subsides;

•our ability to achieve and sustain profitability;

•our ability to generate significant revenue from our marketplace offerings;

•our ability to maintain and grow our community of users;

•the productivity and effectiveness of our sales force;

•the impact of reductions in our workforce or involuntary or voluntary separations, including claims against us from departing employees or others;

•our ability to attract and retain talent that provide the types and quality of services sought by clients on our work marketplace;

•changes in the spending patterns of clients;

•the length and complexity of our sales cycles;

•changes to our pricing model and fee structure, including any resulting changes to our revenue recognition practices;

•fluctuations in gross margin and revenue, including as a result of fluctuations in the use of our managed services offering due to our recognition of the entire GSV from our managed services offering as revenue, including the amounts paid to talent;

•the success of our marketing and brand positioning efforts;

•the impact of changing, consolidating, or terminating offerings and services;

•our ability to respond to competitive developments;

•ongoing uncertainty regarding U.S. and global political conditions;

•our ability to introduce new offerings and services or enhance existing offerings;

•the number of users circumventing our work marketplace and our fees;

•fluctuations in transaction losses;

•the disbursement methods chosen by talent and changes in the mix of disbursement methods offered;

•fluctuations in the prices that talent charge clients on our work marketplace;

•ransomware, data security, or privacy breaches or incidents and associated remediation costs and reputational harm;

•increases in, and timing of, operating expenses that we may incur to grow and expand our operations and to remain competitive;

•seasonality in the labor market and spending patterns by clients and the number of business days and the number of Sundays (i.e., the day we have the contractual right to bill and recognize revenue for the majority of our talent service fees each week) in any given period, as well as local, national, or international holidays;

•litigation, regulatory investigations or enforcement actions, and adverse judgments, settlements, or other litigation-related costs;

•operating lease expenses, other real estate expenses, and any impairment charges on our operating lease asset and related leasehold improvements being recognized as a general and administrative expense due to a reduction to our office space and our potential sublease of such office space at a rental rate that is less than our rent expense for such office space, or any termination fees we may incur as a result of our termination of the operating lease for such office space;

•the impact of sales, use, and other tax laws and regulations in jurisdictions in which we have users;

•changes in the mix of products and services that our enterprise clients or other users demand;

•fluctuations in the mix of payment provider costs and the revenue generated from payment providers;

•potential costs to attract, onboard, retain, and motivate qualified personnel to perform services for us;

•revenue recognition fluctuations for arrangements subject to our tiered pricing model for talent service fees;

•changes in the law, application of the law (including as a result of changes in our services or offerings), or interpretation of law, or in the statutory, legislative, or regulatory environment;

•costs related to the acquisition of businesses, personnel, technologies, or intellectual property;

•the impact of outages of, and other errors, defects or disruptions on, our work marketplace and associated reputational harm;

•the impact of public health pandemics, such as the COVID-19 pandemic, or other global or regional public health events or conditions;

•fluctuations in trade and client receivables due to the timing of cash receipts from clients and the number of transactions on our work marketplace;

•fluctuations in currency exchange rates;

•changes to financial accounting standards and the interpretation of those standards that may affect the way we recognize and report our financial results;

•general economic and political conditions and government regulations in the countries where we currently have significant numbers of users or where we currently operate or may expand in the future;

•losses and expenses from indemnification, dispute assistance, and other contractual obligations we owe to clients; and

•non-cash accounting charges such as stock-based compensation expense, including those related to executive compensation arrangements, and depreciation and amortization.

The impact of one or more of the foregoing and other factors may cause our operating results and performance metrics to vary significantly. As such, we believe that period-to-period comparisons of our operating results and performance metrics may not be meaningful and should not be relied upon as an indication of future performance. For example, future period-over-period growth rates of revenue and key performance metrics such as GSV and active clients, when compared against the quarterly and full year results of 2022, may fail to meet the expectations of investors or securities analysts given the accelerated growth experienced during such periods due to the COVID-19 pandemic and the resulting increased adoption of remote work and reduced seasonality experienced during such periods. If we fail to meet or exceed the expectations of investors or securities analysts, the trading price of our common stock could fall substantially, and we could face costly lawsuits, including securities class action suits.

We track certain performance metrics with internal tools and do not independently verify such metrics. Certain of our performance metrics may not accurately reflect certain details of our business, are subject to inherent challenges in measurement, and real or perceived inaccuracies in such metrics may harm our reputation and negatively affect our business.

We track certain performance metrics, including active clients and GSV per active client, ~~both of which we began reporting in the third quarter of 2021, as well as~~ GSV, and marketplace take rate with internal tools ~~which~~that are not independently verified by any third-party. Our internal tools have a number of limitations and our methodologies for tracking these metrics may change over time, which could result in inaccurate or unexpected changes to our metrics, including the metrics we report. If the internal tools we use to track these metrics undercount or overcount performance or contain algorithmic or other technical errors, the data we report may not be accurate. Our performance metrics

are also impacted by illegal or improper activity on our work marketplace, including fraud, spam, fake accounts, and other activity that violates our terms of service and service agreements. For example, for the three ~~and nine~~ months ended ~~September 30, 2022, we experienced~~March 31, 2023, provision for transaction losses increased, ~~instances of fraud and higher chargeback losses,~~ as compared to the same ~~periods~~period in ~~2021.~~2022, due to fraud protection fees paid to a third-party vendor and increased bad debt losses, instances of fraud, and chargeback losses. These levels of fraud could continue or increase, and there is no assurance that any measures we put in place that are designed to reduce fraud on our work marketplace will be effective. In addition, notwithstanding efforts to identify fake accounts and fraudulent activity on our work marketplace and exclude these users and activity from the calculation of our performance metrics, we are unable to identify and remove all such accounts and activity from being reflected in the performance metrics that we report. Accordingly, our performance metrics may not accurately reflect activity on and the performance of our work marketplace. In addition, limitations or errors with respect to how we measure data, or the accuracy of the data that we measure, may affect our understanding of certain details of our business, which could affect our longer-term strategies and our ability to respond to business trends that may negatively impact our performance. If our performance metrics are not accurate representations of our business, user base, or ~~traffic levels;~~activity on our work marketplace; if we discover material inaccuracies in our metrics; or if the metrics we rely on to track our performance do not provide an accurate measurement of our business, our reputation may be harmed, we may be subject to legal or regulatory actions, and our operating and financial results could be adversely affected. In addition, from time to time we may change the performance metrics that we track, including metrics that we report, and any new performance metrics will also be subject to the foregoing limitations and risks. For example, beginning in the third quarter of 2021, we ceased reporting the performance metrics tracking the number of core clients and client spend retention, and instead began reporting in the third quarter of 2021, the performance metrics tracking the number of active clients and GSV per active client.

~~Our operating results may fluctuate from quarter to quarter, which makes our future results difficult to predict.~~

Our quarterly operating results have fluctuated recently, as they have in the past, and will likely continue to fluctuate in the future, particularly during the current macroeconomic uncertainty and rising interest rates and inflation. Additionally, we have a limited operating history under our current business strategy and pricing model, and we make pricing, product, and other changes from time to time, all of which make it difficult to forecast our future results. As a result, you should not rely upon our past quarterly operating results as indicators of future performance. You should take into account the risks, difficulties, and uncertainties frequently encountered by companies in highly competitive and rapidly evolving markets. Our operating results in any given quarter can be influenced by numerous factors, many of which are unpredictable or are outside of our control, including:

•~~uncertainty regarding demand for our work marketplace as the COVID-19 pandemic subsides and as the current macroeconomic uncertainty continues;~~

•ongoing uncertainty and impact on the global economy and spending by large, medium, and small companies, the shift to remote work, availability of qualified and in-demand talent, and uncertainty regarding the timing and nature of any future macroeconomic downturn, as discussed further below;

•our ability to generate significant revenue from our marketplace offerings, such as our Upwork Enterprise and other premium offerings, including from small- and medium-sized business clients which are most likely to be impacted by the current macroeconomic uncertainty;

•our ability to maintain and grow our community of users, including our ability to acquire large enterprise and other clients with larger, longer-term independent talent needs and qualified and in-demand talent;

•due to our tiered pricing model for talent service fees, the mix in any period between talent that have billed larger amounts to clients on our work marketplace, where we charge a lower rate on billings, and talent that have billed clients less on our work marketplace, where we charge a higher rate on billings;

•~~the success of our marketing and brand positioning efforts;~~

•~~the productivity and effectiveness of our sales force, including our ability to hire and adequately train qualified sales personnel;~~

•our ability to attract and retain talent that provide the types and quality of services sought by clients on our work marketplace, particularly talent that provide services for which client demand exceeds supply on our work marketplace, or, in geographic regions in which clients are seeking to engage remote talent;

•~~the demand for and types and quality of skills and services that are offered on our work marketplace by talent;~~

•spending patterns of clients, including whether those clients that use our work marketplace frequently or for larger projects, reduce their spend, stop using our work marketplace, or change their method of payment to us, including in each case as a result of macroeconomic or other external factors such as increased competition, pricing changes, or the introduction of new or modified offerings or services on our work marketplace, such as changes made in the pricing and packaging of Connects;

•Russia’s invasion of Ukraine, our decision to suspend our business operations in Russia and Belarus, the broad-ranging economic sanctions issued as a result of the invasion, and the current macroeconomic uncertainty;

•~~the length and complexity of our sales cycles;~~

•fluctuations in gross margin and revenue as a result of increased use of our managed services offering due to our recognition of the entire GSV from our managed services offering as revenue, including the amounts paid to talent;

•the impact of consolidating or terminating existing offerings and services, including any associated pricing changes, such as our recent combination of our Upwork Basic and Plus offerings into a single service plan;

•~~our ability to attract, retain, and grow small- and medium-sized business clients;~~

•~~our ability to respond to competitive developments, including new and emerging competitors, pricing changes, and the introduction of new products and services by our competitors;~~

•ongoing uncertainty regarding U.S. and global political conditions, including military conflicts in geographic locations where a portion of our remote workforce and a large number of our users reside, such as in Ukraine;

•~~our ability to generate a profit and significant revenue from new offerings and services;~~

•~~our ability to introduce new offerings and services or enhance existing offerings, including modernizing our technology, and services without adversely affecting our existing revenue;~~

•changes to our offerings and pricing model, including associated fees, and any resulting change in our ability to generate revenue, such as the pricing and packaging of Connects purchases and our consolidation of our Upwork Basic and Plus offerings, how we recognize revenue, or changes in user behavior in response to such changes;

•~~the number of users circumventing our work marketplace and our fees, which could increase during macroeconomic downturns or as a result of changes to our pricing model;~~

•~~fluctuations in transaction losses;~~

•~~the disbursement methods chosen by talent and changes in the mix of disbursement methods offered;~~

•fluctuations in the prices that talent charge clients on our work marketplace, including as a result of a rise in inflation, which may impact the amount of revenue we recognize as a percentage of GSV due to our tiered pricing model for talent service fees;

•~~ransomware, data security, or privacy breaches or incidents and associated remediation costs and reputational harm;~~

•increases in, and timing of, operating expenses that we may incur to grow and expand our operations and to remain competitive, such as advertising and other marketing expenses, including those associated with evolving our brand positioning and as we seek to grow our international user base;

•seasonal spending patterns by clients or work patterns by talent, seasonality in the labor market, exaggerated impact of typical seasonality in the labor market (for example, extended vacations during the summer and holiday seasons), as the COVID-19 pandemic subsides and the resulting relaxation or lifting of restrictions intended to prevent the spread of COVID-19, as well as the number of business days, the number of Mondays (i.e., the day we have the contractual right to bill and recognize revenue for a substantial portion of our client fees each week) or the number of Sundays (i.e., the day we have the contractual right to bill and recognize revenue for the majority of our talent service fees each week) in any given quarter, as well as local, national, or international holidays;

•~~spending patterns and project bidding behavior of talent with respect to the offerings and services available to them on our work marketplace, such as membership fees and Connects purchases;~~

•~~revenue recognition fluctuations for arrangements subject to our tiered pricing model for talent service fees;~~

•~~litigation, regulatory investigations or enforcement actions, and adverse judgments, settlements, or other litigation-related costs;~~

•any impairment charges on our operating lease asset and related leasehold improvements being recognized as a general and administrative expense due to a reduction to our office space and our potential sublease of such office space at a rental rate that is less than our rent expense for such office space, or any termination fees we may incur as a result of our termination of the operating lease for such office space. For example, as a result of our shift to a flexible work model for our workforce, in 2021 we subleased the entirety our former headquarters in Santa Clara, California and a portion of our current headquarters in San Francisco, California, and, as a result, we incurred impairment charges of $8.7 million;

•the impact of sales, use, and other tax laws and regulations in jurisdictions in which we have users, including the requirement in certain jurisdictions to collect indirect taxes on user fees, to withhold and remit taxes related to income or earnings, or to pay any such taxes or resulting penalties as a result of our failure to comply with such requirements;

•~~changes in the mix of products and services that our enterprise clients or other users demand;~~

•~~fluctuations in the mix of payment provider costs and the revenue generated from payment providers;~~

•~~potential costs to attract, onboard, retain, and motivate qualified personnel to perform services for us;~~

•changes in the law, application of the law (including as a result of changes in our services or offerings), or interpretation of law, or in the statutory, legislative, or regulatory environment, such as with respect to privacy, data security, wage and hour regulations, worker classification (including classification of independent contractors or similar workers and classification of employees as exempt or non-exempt), internet regulation, payments, payment processing, global trade, or tax obligations;

•~~the episodic nature of freelance work generally or changes to demand for freelance work or interest in freelancing due to political or regulatory changes or uncertainty;~~

•~~costs related to the acquisition of businesses, personnel, technologies, or intellectual property, including potentially significant amortization costs and possible write-downs;~~

•~~the cost and time needed to develop and upgrade our work marketplace to incorporate new technologies or develop new or improved offerings;~~

•~~the impact of outages of, and other errors, defects or disruptions on, our work marketplace and associated reputational harm;~~

•~~the impact of public health pandemics, especially the COVID-19 pandemic, or other global or regional events or conditions;~~

•~~fluctuations in trade and client receivables due to the timing of cash receipts from clients and the number of transactions on our work marketplace;~~

•~~changes in the mix of countries in which our users are located, which impacts the amount of revenue we derive from currency exchange;~~

•~~the impact of reductions in our workforce or involuntary or voluntary separations, including claims against us from departing employees or others;~~

•~~fluctuations in currency exchange rates;~~

•changes to financial accounting standards and the interpretation of those standards that may affect the way we recognize and report our financial results, including changes in accounting rules governing recognition of revenue;

•~~general economic and political conditions and government regulations in the countries where we currently have significant numbers of users or where we currently operate or may expand in the future;~~

•~~operating lease expenses and other real estate expenses;~~

•~~lease termination fees or rent expense that is in excess of sublease income for a particular office space;~~

•~~losses and expenses from indemnification, dispute assistance, and other contractual obligations we owe to clients; and~~

•~~non-cash accounting charges such as stock-based compensation expense, including those related to executive compensation arrangements, and depreciation and amortization.~~

The impact of one or more of the foregoing and other factors may cause our operating results and performance metrics to vary significantly. As such, we believe that quarter-to-quarter comparisons of our operating results and performance metrics may not be meaningful and should not be relied upon as an indication of future performance. For example, future period-over-period growth rates of revenue and key performance metrics such as GSV and active clients, when compared against the quarterly and full year results of 2021, may fail to meet the expectations of investors or securities analysts given the accelerated growth experienced during such periods due to the COVID-19 pandemic and the resulting increased adoption of remote work and reduced seasonality experienced during such periods. If we fail to meet or exceed the expectations of investors or securities analysts, the trading price of our common stock could fall substantially, and we could face costly lawsuits, including securities class action suits.

If we fail to maintain an effective system of disclosure controls and internal control over financial reporting, our ability to produce timely and accurate financial statements or comply with applicable laws and regulations could be impaired.

A material weakness is a deficiency or combination of deficiencies in our internal control over financial reporting such that there is a reasonable possibility that a material misstatement of our consolidated financial statements would not be prevented or detected on a timely basis. As previously disclosed, we identified a number of adjustments relating to previously issued consolidated financial statements that resulted in a revision to our consolidated financial statements as of and for the year ended December 31, 2016 and determined that this control deficiency constituted a material weakness in our internal control over financial reporting. We successfully remediated the material weakness during the year ended December 31, 2020.

If we experience additional material weaknesses or otherwise fail to maintain an effective system of internal controls in the future, we may not be able to accurately or timely report our financial condition or results of operations or prevent fraud, which may adversely affect investor confidence in us and, as a result, the value of our common stock. We cannot assure you that all of our existing material weaknesses have been identified, or that we will not in the future identify additional material weaknesses. Any failure to maintain effective disclosure controls and internal control over financial reporting could have an adverse effect on our business and results of operations and could adversely impact our business, operating results, and financial condition.

If we are unable to assert that our internal control over financial reporting is effective, or if our independent registered public accounting firm is unable to express an opinion on the effectiveness of our internal control, we could lose investor confidence in the accuracy and completeness of our financial reports, which would cause the price of our common stock to decline, and we may be subject to investigation or sanctions by the SEC. Furthermore, investor perceptions of our company may suffer if, in the future, material weaknesses are found, and this could cause the price of our common stock to decline. In addition, if we are unable to continue to meet these requirements, we may not be able to remain listed on The Nasdaq Global Select Market.

If currency exchange rates fluctuate substantially in the future, the results of our operations, which are reported in U.S. dollars, could be adversely affected.

As we expand our international footprint and make more services available to our users internationally, we will become more exposed to the effects of fluctuations in currency exchange rates. Although we expect

an increasing number of sales contracts to be denominated in currencies other than the U.S. dollar in the future, all of our sales contracts are and have historically been denominated in U.S. dollars. However, we offer clients the option to settle invoices denominated in U.S. dollars in the local currencies of several non-U.S. countries, and therefore, a portion of our revenue is subject to foreign currency risk. While we currently use derivative instruments to hedge certain exposures to fluctuations in foreign currency exchange rates, the use of such hedging activities may not offset any, or more than a portion, of the adverse financial effects of unfavorable movements in foreign exchange rates over the limited time the hedges are in place. Moreover, geopolitical or macroeconomic events may also cause volatility in currency exchange rates between the U.S. dollar and other currencies, such as the Euro. For example, the risk of a U.S. political crisis leading to a default on U.S. sovereign debt may cause large-scale fluctuations in the value of the U.S. dollar that could make hedging instruments more expensive or less available and could make U.S. dollar-denominated contracts less desirable for clients or freelancers located outside the United States. Additionally, a strengthening of the U.S. dollar, as we ~~are currently experiencing,~~experienced in 2022, could increase the real cost of transacting on our work marketplace to clients located outside of the United States and could result in a loss of such clients or a portion of their spend, which could adversely affect our business, operating results, financial condition, and cash flows.

The applicability of sales, use, and other tax laws or regulations on our business ~~is uncertain. Adverse tax laws or regulations could be enacted or existing laws could be interpreted as applying or otherwise applied to us or users of our work marketplace, which~~ could subject us or our users to additional tax liability and related interest and penalties, and adversely impact our business.

The application of federal, state, local, and international tax laws to services provided over the internet is evolving. In addition to income taxes, in the United States and various foreign jurisdictions, we may also be subject to non-income basedindirect taxes, such as ~~payroll,~~ sales and use tax, value-added ~~and~~tax, goods and services ~~taxes (including~~tax, business tax, gross receipt tax, and digital services tax, and the ~~“digital service tax”),~~tax information reporting obligations to our businesses are complex and ~~we may also be~~evolving. Significant judgment is required to evaluate applicable tax obligations, and, as a result, amounts recorded are estimates and are subject to ~~increased obligations as a withholding agent. Many of~~adjustments. In many cases, the ~~fundamental~~ultimate tax determination is uncertain because it is not clear how new and existing statutes ~~and regulations that impose these taxes were established before the adoption and growth of the internet and ecommerce. In addition, governments are increasingly looking for ways~~might apply to increase revenue, which has resulted in aggressive enforcement and new interpretations of existing tax laws, enacting new laws and promulgating new regulations (particularly those establishing an economic nexus as a basis to collect taxes from companies with no local presence), discussions about tax reform, and other legislative action to increase tax revenue, including through indirect taxes. New income, payroll, sales, use, value-added, goods and services, platform, intermediary, digital services, or other tax laws, statutes, rules, regulations, or ordinances are regularly enacted and could be enacted at any time (possibly with retroactive effect), could be applied solely or disproportionately to services provided over the internet, could target certain offerings and services offered on our ~~work marketplace, or could otherwise affect our or our users’ tax obligations or financial position and operating results.~~business. For example, a number of U.S. states and other jurisdictions have ~~within the past few years,~~ enacted taxes and tax collection obligations on marketplace facilitators, requiring online marketplaces to collect and remit taxes for first- and third-party sales on their websites. A successful assertion that we should be collecting taxes or remitting taxes directly to states or other jurisdictions beyond those that we already collect or remit could result in substantial tax liabilities for past transactions and additional administrative expenses, and could cause us to accrue additional estimates of taxes due, including interest and penalties. Moreover, many countries in the EU, as well as the United Kingdom, India, and a number of other countries and organizations, such as the Organisation for Economic Co-operation and Development, have recently proposed or recommended changes to existing tax laws or have enacted new laws that could impact our tax obligations. The impact and burden of these regulations and proposed regulations on our business and the businesses of our users is uncertain ~~but~~and may have a negative impact on our business.

~~We currently report, collect,~~Starting on January 1, 2023, all businesses that process payments became required to issue a Form 1099-K for all talent who receive $600 or more in payments, a significant decrease from the previous reporting threshold of $20,000 and ~~remit~~200 transactions. The Form 1099-Ks for the new thresholds will be issued in January 2024. There is a risk of similar laws being enacted by other jurisdictions in the future. Tax collection responsibility and the additional costs associated with complex indirect ~~taxes~~tax collection, remittance and audit requirements, in addition to reporting requirements, could create additional tax exposure for us and additional burdens for users on our ~~fees~~websites and mobile platforms.

We may also be subject to additional tax liabilities and related interest and penalties due to: changes in ~~a number of~~federal, state, and international tax laws, statutes, rules, regulations, or ordinances; changes in taxing jurisdictions and administrative interpretations, decisions, policies, and applications; results of tax examinations, settlements, or judicial decisions; changes in accounting principles; changes to our business operations; and changes in tax positions taken in prior periods. Such changes could adversely impact us or our users (possibly with retroactive effect), which could require us or our users to pay additional tax amounts on prior sales and going forward, as well as require us or our users to pay fines, penalties, and interest for past amounts. For example, if we are treated as an agent for users on our work marketplace under U.S. state tax law, we may ~~begin reporting,~~be primarily responsible for collecting and remitting ~~indirect taxes in additional jurisdictions. Our reporting and collection of indirect taxes on our fees in these jurisdictions may increase our costs or costs of our users,~~sales

7666

~~which may cause our users~~taxes directly to ~~circumvent our work marketplace~~certain states. It is possible that one or more states could seek to impose sales, use, ~~other platforms~~ or other ~~alternatives~~tax collection obligations on us with regard to transactions on our platform. These taxes may be applicable to past sales. A successful assertion by a taxing authority that ~~do not collect indirect~~we should be collecting additional sales, use, or other taxes ~~on their fees. In addition,~~or remitting such taxes directly to states could result in substantial tax liabilities for past sales and additional administrative expenses, which could negatively impact our business.

Any changes to our business operations, including international expansions, internal reorganizations, and transfer pricing could impact our tax liabilities. The taxing authorities of the jurisdictions in which we operate may ~~raise questions about,~~ challenge our methodologies for pricing intercompany transactions pursuant to the intercompany arrangements or disagree with our ~~determination~~determinations as to ~~whether~~the income and expenses attributable to specific jurisdictions or specific affiliates. If such a challenge or disagreement were to occur, and our position was not sustained, we ~~are obligated~~could be required to ~~collect indirect taxes or our calculation, reporting, or collection of taxes and may require us to remit~~pay additional taxes, ~~and~~ interest, and could impose associated penalties and fees. Should any new taxes become applicable or the application of existing taxes be deemed to apply to us or our users, or if the taxes we pay are found to be deficient, our business could be adversely impacted. penalties.

We have in the past been, and may in the future be, audited by tax authorities with respect to non-income taxes, and we may have exposure to additional non-income tax liabilities, which could have an adverse effect on our operating results and financial condition. In addition, our future effective tax rates could be favorably or unfavorably affected by changes in tax rates, changes in the valuation of our deferred tax assets or liabilities, the effectiveness of our tax planning strategies, or changes in tax laws or their interpretation. Such changes could have an adverse impact on our operating results and financial condition.

Moreover, state, local, and foreign tax jurisdictions have differing rules and regulations governing reporting, sales, income, use, value-added, payroll, services, and other taxes, and these rules and regulations can be complex and are subject to varying interpretations and enforcement positions that may change over time. Existing tax laws, statutes, rules, regulations, or ordinances could be interpreted, changed, modified, or applied adversely to us or our users (possibly with retroactive effect), which could require us or our users to pay additional tax amounts on prior sales and going forward, as well as require us or our users to pay fines, penalties, and interest for past amounts. Although our terms of service require our users to pay all applicable sales and other taxes and to indemnify us for any requirement that we pay any withholding amount to the appropriate authorities, our work marketplace does not include functionality to easily enable users to charge any applicable taxes to one another, users may be unwilling or unable to pay back taxes and associated interest or penalties and may fail to indemnify us, we may determine that it would not be commercially feasible or cost-effective to seek reimbursement, the indemnification obligation may be deemed unenforceable, or the functionality and indemnification provisions may cause users to seek out other platforms. If we are required to collect and pay back taxes and associated interest and penalties, or we are unsuccessful in collecting such amounts from our users, we could incur potentially substantial unplanned expenses, thereby adversely impacting our operating results and cash flows. In addition, tax laws and regulations may subject us to audit by tax regulators and require us to provide certain data and information, including user information, from our work marketplace to tax regulators in certain jurisdictions. If we are obligated to provide such information to tax regulators in any jurisdiction, users may choose to use other platforms or other alternatives, which may in turn adversely affect our operating results and financial condition.

Also, federal and state tax rules require collection of certain data and reporting transactions or payments above certain thresholds. Under certain circumstances, a failure to comply with such reporting obligations may cause us to become liable to withhold a percentage of the amounts paid to talent and remit such amounts to the taxing authorities. Due to the large number of users and transaction volume on our platform, process failures with respect to these data collection or reporting obligations could result in financial liability and other consequences to us if we were unable to remedy such failures in a timely manner.

Additionally, our corporate structure and intercompany arrangements are subject to the tax laws of various jurisdictions, and we could be obligated to pay additional taxes, which could adversely impact our operating results. The taxing authorities of the jurisdictions in which we operate may challenge our methodologies for pricing intercompany transactions pursuant to the intercompany arrangements or disagree with our determinations as to the income and expenses attributable to specific jurisdictions or specific affiliates. If such a challenge or disagreement were to occur, and our position was not sustained, we could be required to pay additional taxes, interest, and penalties.

We accrue liabilities related to tax obligations on our consolidated financial statements based on our best estimate of these liabilities, however, the ultimate amount of tax obligations we owe may differ from the amounts recorded in our financial statements and any such difference may adversely impact our

~~operating results in future periods in which we change our estimates of our tax obligations or in which the ultimate tax outcome is determined.~~

Our ability to use our net operating loss carryforwards and certain other tax attributes is limited.

As of December 31, ~~2021,~~2022, we had net operating loss, which we refer to as NOL, carryforwards for U.S. federal income tax purposes and California state income tax purposes of ~~$444.6~~$341.4 million and ~~$90.4~~$95.0 million, respectively, available to offset future taxable income. ~~Our~~The federal ~~net operating loss carryforward amounts began~~NOLs generated in the years ended December 31, 2004 through 2017 will begin to expire in ~~2019, including $14.5 million that expired in 2019, $15.1 million that expired in 2020, and $21.6 million that expired in 2021, and will continue to expire in 2022 and future years.~~2024. The California state ~~net operating loss~~NOL carryforward amounts will begin to expire in 2028. Realization of these ~~net operating loss~~NOL carryforwards depends on future income, and there is a risk that our existing carryforwards could expire unused and be unavailable to offset future income tax liabilities, which could materially and adversely affect our operating results.

In ~~addition,~~general, under ~~Sections~~Section 382 ~~and 383~~ of the Internal Revenue Code of 1986, as amended, if a corporation that undergoes an “ownership change,” generally defined as a greater than 50% change (by value) in its equity ownership over a three-year period, ~~the corporation’s~~is subject to limitations on its ability to ~~use~~utilize its pre-change ~~net operating loss~~NOL carryforwards ~~and other pre-change tax attributes, such as research tax credits,~~ to offset ~~its post-change income~~future taxable income. We may ~~be limited. In addition, we may experience~~have undergone ownership changes in the past, which could result in limitations on our ability to utilize our NOLs, or future ~~as a result of subsequent shifts~~changes in our stock ~~ownership. As~~ownership, some of which are outside of our control, could result in an ownership change under Section 382. There is also a ~~result,~~risk that due to regulatory changes, such as suspensions on the use of NOLs or other unforeseen reasons, our existing NOLs could expire or otherwise be unavailable to offset future U.S. federal and state taxable income. For these reasons, we may not be able to utilize some portion of our NOLs even if we ~~earn net taxable income, our ability to use our pre-change net operating loss carry-forwards and other tax attributes to offset U.S. federal taxable income may be subject to limitations,~~attain profitability, which could potentially result in increased future tax liability to us.

In addition, the Tax Cuts and Jobs Act, as modified by the Coronavirus Aid, Relief, and Economic Security Act, limits the utilization of NOLs arising in taxable years beginning after December 31, 2017 to 80% of taxable income in any taxable year beginning after December 31, 2020. NOLs arising in taxable years beginning after December 31, 2017 can be carried forward indefinitely with no carryback allowed. As we maintain a full valuation allowance against our U.S. federal and state NOLs, these charges did not impact our consolidated balance sheet as of December 31, 2022. However, in future years, at the time a deferred tax asset is recognized related to our NOLs, the charges in the carryforward/carryback periods as well as new limitations on use of NOLs may significantly impact our valuation allowance assessments.

We may require additional capital to fund our business and support our growth, including in connection with any future acquisitions or strategic investments, and any inability to generate or obtain such capital may adversely affect our operating results and financial condition.

In order to support our growth and respond to business challenges, such as developing new features or enhancements to our work marketplace, acquiring new technologies, and improving our infrastructure, we

have made significant financial investments in our business, and we intend to continue to make such ~~investments.~~investments in the future. In addition, we may, from time to time, seek to acquire or strategically invest in other complementary products, technologies, or ~~businesses. As a result,~~businesses or repurchase outstanding shares of our common stock or the Notes. For example, we paid $170.8 million to consummate the Repurchases in March 2023. We may need to engage in equity or debt financings to obtain the funds required for these investments, acquisitions, and other business endeavors. If we raise additional funds through equity or convertible debt issuances, our existing stockholders may suffer significant dilution and these securities could have rights, preferences, and privileges that are superior to those of holders of our common stock. If we obtain additional funds through debt financing, we may not be able to obtain such financing on terms favorable to us. Such terms may involve additional restrictive covenants making it difficult to engage in capital raising activities and pursue business opportunities, including potential acquisitions and strategic investments. If we are unable to obtain adequate financing or financing on terms satisfactory to us when we require it, our ability to continue to support our business growth and to respond to business challenges could be significantly impaired and our business may be adversely affected, requiring us to delay, reduce, or eliminate some or all of our operations.

Risks Related to Ownership of Our Common Stock

The stock price of our common stock has been and may continue to be volatile, and you could lose all or part of your investment.

The market price of our common stock has been and may continue to be volatile, particularly as a result of broader stock market fluctuations and in light of the current macroeconomic uncertainty. The market price of our common stock may fluctuate significantly in response to numerous factors, ~~many of which are beyond our control and some of which will be impacted by Russia’s invasion of Ukraine, the COVID-19 pandemic, and the current macroeconomic uncertainty,~~ including:

•actual or anticipated fluctuations in our revenue, measures of profitability, and other financial and operating results or our failure to meet the estimates of securities analysts or the expectations of investors;

•the financial projections we provide to the public or our failure to meet these projections;

•overall performance of the equity markets, including as a result of unfavorable investor sentiment toward unprofitable companies;

•the economy as a whole and market conditions in our industry;

•negative publicity related to the real or perceived trustworthiness, quality, or security of our work ~~marketplace, as well as~~ marketplace;

•the failure to timely launch new offerings and services that gain market acceptance;

•recruitment or departure of key personnel;

•rising interest rates and inflation;

•financial turmoil or instability affecting the banking system or financial markets;

•failure of securities analysts to initiate or maintain coverage of us, inaccurate or unfavorable research by analysts, or changes in financial estimates by any securities analysts who follow our company;

•repurchases by us of any of our outstanding shares of common stock or the Notes, on unfavorable terms or at all;

•speculative trading practices by stockholders and other market participants;

•rumors and market speculation involving us or other companies in our industry and/or other industries;

•lawsuits threatened or filed against or by us or against our key personnel, litigation involving our industry, or lawsuits threatened or filed against our users relating to their use of our work marketplace;

•increased interest and trading in our stock from retail investors;

•developments or disputes concerning our or other parties’ products, services, or intellectual property rights;

•acquisitions, strategic partnerships, joint ventures, or capital commitments;

•sales of shares of our common stock by us or our stockholders, including sales of large blocks of our stock relative to the size of our public float;

•new laws or regulations or new interpretations of existing laws or regulations applicable to our business, including those governing worker classification, taxation of workers, or withholding and remitting taxes on income or earnings;

•announcements by us or our competitors of new or terminated products or services, commercial relationships, or significant technical innovations;

•changes in accounting standards, policies, guidelines, interpretations, or principles;

•political changes or events, such as the ongoing U.S. and global political and international relations environment; and

•other events or factors, including those resulting from war, incidents of terrorism, or responses to these events, including our decision to suspend business operations in Russia and ~~Belarus.~~Belarus and the ongoing war in Ukraine.

In addition, the stock markets have experienced extreme price and volume fluctuations that have affected and continue to affect the market prices of equity securities of many ~~companies. Stock prices of many companies,~~ technology companies and unprofitable companies in particular, have fluctuated in a manner unrelated or disproportionate to the operating performance of those companies and are attributable, in part, to outside factors such as Russia’s invasion of Ukraine and the COVID-19 pandemic and their impact on the global economy, including rising interest rates.companies. In the past, stockholders have instituted securities class action litigation following periods of market volatility. If we were to become involved in

securities litigation, it could subject us to substantial costs, divert resources and the attention of management from our business, and adversely affect our business.

Sales of substantial amounts of our common stock in the public markets, particularly sales by our directors, executive officers, and significant stockholders, or the perception that these sales could occur, could cause the market price of our common stock to decline and may make it more difficult for you to sell your common stock at a time and price that you deem appropriate.

The market price of our common stock could decline as a result of sales of a large number of shares of our common stock in the market, particularly sales by our directors, executive officers, and significant stockholders. The perception that these sales might occur may also cause the market price of our common stock to decline. All shares of our common stock are freely tradable, generally without restrictions or further registration under the Securities Act of 1933, as amended, which we refer to as the Securities Act, subject to certain exceptions for shares held by our “affiliates” as defined in Rule 144 under the Securities Act. In addition, the shares issued upon exercise of outstanding stock options or settlement orof outstanding restricted stock units will be available for immediate resale in the United States on the open market.

Moreover, certain holders of our common stock have rights, subject to certain conditions, to require us to file registration statements for the public resale of such shares or to include such shares in registration statements that we may file for us or other stockholders.

We may also issue our shares of common stock or securities convertible into shares of our common stock from time to time in connection with a financing, an acquisition, investments, or otherwise. We will also grant additional equity awards to employees, directors, and consultants under our 2018 Equity Incentive Plan and rights to purchase our common stock under our 2018 Employee Stock Purchase Plan. Any such issuances could result in substantial dilution to our existing stockholders and cause the market price of our common stock to decline.

We do not intend to pay dividends for the foreseeable future.

We have never declared or paid any cash dividends on our common stock and do not intend to pay any cash dividends in the foreseeable future. We anticipate that for the foreseeable future we will retain all of our future earnings for use in the development of our business and for general corporate purposes. ~~Any determination to pay dividends in the future will be at the discretion of our board of directors.~~ Accordingly, investors must rely on sales of their common stock after price appreciation, which may never occur, as the only way to realize any future gains on their investments.

Provisions in our charter documents and under Delaware law could make an acquisition of our company more difficult, limit attempts by our stockholders to replace or remove our current management, limit our stockholders’ ability to obtain a favorable judicial forum for disputes with us or our directors, officers, or employees, and limit the market price of our common stock.

Provisions in our restated certificate of incorporation and amended and restated bylaws may have the effect of delaying or preventing a change of control or changes in our management. Our restated certificate of incorporation and amended and restated bylaws include provisions that:

•provide that our board of directors is classified into three classes of directors with staggered three-year terms;

•permit the board of directors to establish the number of directors and fill any vacancies and newly created directorships;

•require super-majority voting to amend some provisions in our restated certificate of incorporation and amended and restated bylaws;

•authorize the issuance of “blank check” preferred stock that our board of directors could use to implement a stockholder rights plan (also known as a “poison pill”);

•provide that only the chairperson of our board of directors, our chief executive officer, president, lead independent director, or a majority of our board of directors will be authorized to call a special meeting of stockholders;

•prohibit stockholder action by written consent, which requires all stockholder actions to be taken at a meeting of our stockholders;

•provide that the board of directors is expressly authorized to make, alter, or repeal our amended and restated bylaws; and

•establish advance notice requirements for nominations for election to our board of directors or for proposing matters that can be acted upon by stockholders at annual stockholder meetings.

In addition, our restated certificate of incorporation provides that the Court of Chancery of the State of Delaware is the exclusive forum for any derivative action or proceeding brought on our behalf, any action asserting a breach of fiduciary duty, any action asserting a claim against us arising pursuant to the Delaware General Corporation Law, which we refer to as the DGCL, our restated certificate of incorporation, or our amended and restated bylaws, or any action asserting a claim against us that is governed by the internal affairs doctrine. Our amended and restated bylaws also provide that the federal district courts of the United States would be the exclusive forum for resolving any complaint asserting a cause of action arising under the Securities Act. Any person or entity purchasing or otherwise acquiring any interest in any of our securities shall be deemed to have notice of and consented to this provision.

These choice of forum provisions may limit a stockholder’s ability to bring a claim in a judicial forum that it finds favorable for disputes with us or any of our directors, officers, or other employees, which may discourage lawsuits against us and our directors, officers, and other employees.

Moreover, Section 203 of the DGCL may discourage, delay, or prevent a change of control of our company. Section 203 imposes certain restrictions on mergers, business combinations, and other transactions between us and holders of 15% or more of our common stock.

Risks Related to Our Convertible Senior Notes

Our indebtedness could limit the cash flow available for our operations and expose us to risks that could adversely affect our business, financial condition, and results of operations.

In August 2021, we issued ~~the Notes, which have an~~$575.0 million aggregate principal amount of ~~$575.0 million.~~the Notes. The Notes are senior, unsecured obligations and bear interest at a rate of 0.25% per year. The Notes will mature on August 15, 2026, unless earlier redeemed, repurchased, or converted in accordance with the terms of the Notes. In March 2023, we consummated the Repurchases, repurchasing $214.0 million aggregate principal amount of the Notes. As of ~~September 30, 2022,~~March 31, 2023, we had ~~$575.0~~$361.0 million aggregate principal amount of ~~indebtedness.~~the Notes outstanding. We may also incur additional indebtedness to meet future financing needs. Our indebtedness could have significant negative consequences for our stockholders and our business, results of operations and financial condition by, among other things:

•increasing our vulnerability to adverse economic and industry conditions;

•limiting our ability to obtain additional financing;

•requiring the dedication of a substantial portion of our cash flow from operations to service our indebtedness, which will reduce the amount of cash available for other purposes;

•limiting our flexibility to plan for, or react to, changes in our business;

•diluting the interests of our existing stockholders as a result of issuing shares of our common stock upon conversion of the Notes; and

•placing us at a possible competitive disadvantage with competitors that are less leveraged than us or have better access to capital.

Our business may not generate sufficient funds, and we may otherwise be unable to maintain sufficient cash reserves, to pay amounts due under our indebtedness and our cash needs may increase in the future.

The capped call transactions may affect the value of our common stock.

In connection with the Notes, we entered into the privately negotiated Capped Calls with various financial institutions, which we refer to as the option counterparties. The Capped Calls remain in effect notwithstanding the Repurchases. The Capped Calls are expected generally to reduce the potential dilution to our common stock upon any conversion of the Notes and/or offset any potential cash payments we are required to make in excess of the principal amount upon conversion of any Notes, with such reduction and/or offset subject to a cap.

In addition, the option counterparties and/or their respective affiliates may modify their hedge positions by entering into or unwinding various derivatives with respect to our common stock and/or purchasing or selling our common stock in secondary market transactions (and are likely to do so following any conversion of Notes, any repurchase of the Notes by us on any fundamental change repurchase date, any redemption date, or any other date on which the Notes are retired by us). This activity could also cause or avoid an increase or a decrease in the market price of our common stock.

The potential effect, if any, of these transactions and activities on the market price of our common stock will depend in part on market conditions and cannot be ascertained at this time. Any of these activities could adversely affect the value of our common stock.

General Risks

Adverse or changing economic conditions may negatively impact our business.

Our business depends on the overall demand for labor and on the economic health of current and prospective clients that use our work marketplace. Any significant weakening of the economy in the United States or Europe or of the global economy, as is currently anticipated or otherwise, including the ~~worsening of the ongoing labor shortage or the~~ continued rise in inflation, hiring freezes, layoffs, more limited availability of credit, a reduction in business confidence and activity, decreased government or business spending, economic and political uncertainty,

financial turmoil or instability affecting the banking system or financial markets, trade wars, sanctions, ~~and~~ higher tariffs, global or regional public health events or conditions, a more limited market for independent professional service providers or information technology services, shifts away from remote work, including as companies bring workers back to physical offices following the COVID-19 pandemic, and other adverse economic or market conditions may adversely impact our business and operating results. Further, global economic and political events or uncertainty, such as Russia’s invasion of Ukraine, has caused, and may continue to cause, some of our current or potential users to curtail their use of our work marketplace, and may ultimately result in new regulatory and cost challenges to our operations, including sanctions imposed in response to such events. See the risk factor titled “Russia’s invasion of Ukraine and our decision to suspend our business operations in Russia and Belarus have affected and may continue to affect our business and results of operations” above for additional information. In addition, small- and medium-sized businesses were disproportionately impacted by the macroeconomic downturn caused by the COVID-19 pandemic, some of which reduced their spend on our work marketplace. These adverse conditions have resulted in the past, and may again result, in reductions in revenue, increased operating expenses, longer sales cycles, and increased competition. There is also a risk that when overall global economic conditions are positive, our business could be negatively impacted by a decreased demand for talent as businesses utilize more full-time employees relative to their use of independent contractors. We cannot predict the timing, strength, or duration of any economic slowdown, or any subsequent recovery generally. If the conditions in the general economy continue to deteriorate, ~~as a result of Russia’s invasion of Ukraine, the COVID-19 pandemic, or otherwise,~~ our business, financial condition, and operating results could be adversely affected.

We may be adversely affected by natural disasters and other catastrophic events ~~including the ongoing COVID-19 pandemic,~~or by man-made problems such as warfare or terrorism, or failures of technology that could disrupt our business operations, and our business continuity and disaster recovery plans may not adequately protect us from a serious disaster.

A significant natural disaster, such as an earthquake, blizzard, hurricane, fire, flood, or other catastrophic event, such as a power loss or telecommunications failure, or other technological failure resulting in the permanent destruction of data, could have a material adverse impact on our business, financial condition, and operating results. In the event of natural disaster or other catastrophic event, we may be unable to

continue our operations and may endure system interruptions, reputational harm, delays in development of our work marketplace, lengthy interruptions in service, security breaches, and loss of critical data, all of which could have an adverse effect on our operating results. Certain of our departments are situated primarily in one geographical area and any natural disaster or catastrophic event to such area or the surrounding communities where our employees live may impact productivity or revenue generating activities by employees based in that office. Our corporate headquarters and many key personnel are located in the San Francisco Bay Area, a region known for seismic activity and catastrophic fires. In addition, natural disasters and other catastrophic events could affect our partners’ ability to perform services for users on a timely basis. In the event any such partners’ information technology systems or service abilities are hindered by any of the events discussed above, our ability to provide our work marketplace and other services may be impaired, resulting in missing financial targets for a particular quarter or year, or longer period. Further, if a natural disaster or other catastrophic event occurs in a region from which we derive a significant portion of our revenue, users in that region may delay or ~~forego~~forgo use of our work marketplace or other services, which may adversely impact our operating results. In addition, acts of terrorism, civil disorder, public health pandemics ~~(including~~(such as the COVID-19 pandemic), or military conflict (including ~~Russia’s invasion of~~the war in Ukraine) have caused and could again cause disruptions in our business or the business and activity of our partners, users, or the economy as a whole. These disruptions may be more severe than in the case of natural disasters. All of the aforementioned risks may be exacerbated if our or our partners’ business continuity and disaster recovery plans prove to be inadequate. To the extent that any of the above results in delays or reductions in platform availability, activities or other services, our business, financial condition, and operating results would be adversely affected.

Item 2. Unregistered Sales of Equity Securities and Use of Proceeds.

None.

Item 3. Defaults Upon Senior Securities.

None.

Item 4. Mine Safety Disclosures.

Not applicable.

Item 5 . Other Information.

None.

Item 6. Exhibits.


Exhibit Number	Description	Incorporated by Reference	Filed Herewith
10.1#	~~Transition and Separation Agreement,~~Offer Letter, dated ~~September 21, 2022,~~March 22, 2023, by and between Upwork Inc. and ~~Jeff McCombs~~Erica Gessert.		~~(material terms of which were previously described~~X
10.2#	Change in ~~the Form 8-K filed~~Control and Severance Agreement, dated April 25, 2023, by and between Upwork Inc. ~~on September 22, 2022).~~and Erica Gessert.		X
31.1	Certification of Principal Executive Officer Pursuant to Rules 13a-14(a) and 15d-14(a) under the Securities Exchange Act of 1934, as Adopted Pursuant to Section 302 of the Sarbanes-Oxley Act of ~~2002.~~2002.		X
31.2	Certification of Principal Financial Officer Pursuant to Rules 13a-14(a) and 15d-14(a) under the Securities Exchange Act of 1934, as Adopted Pursuant to Section 302 of the Sarbanes-Oxley Act of ~~2002.~~2002.		X
32.1*	Certification of Principal Executive Officer Pursuant to 18 U.S.C. Section 1350, as Adopted Pursuant to Section 906 of the Sarbanes-Oxley Act of ~~2002.~~2002.		X
32.2*	Certification of Principal Financial Officer Pursuant to 18 U.S.C. Section 1350, as Adopted Pursuant to Section 906 of the Sarbanes-Oxley Act of 2002.		X
101.INS	Inline XBRL Instance Document (the instance document does not appear in the Interactive Data File because its XBRL tags are embedded within the Inline XBRL document).		X
101.SCH	Inline XBRL Taxonomy Extension Schema Document.		X
101.CAL	Inline XBRL Taxonomy Extension Calculation Linkbase Document.		X
101.DEF	Inline XBRL Taxonomy Extension Definition Linkbase Document.		X
101.LAB	Inline XBRL Taxonomy Extension Label Linkbase Document.		X
101.PRE	Inline XBRL Taxonomy Extension Presentation Linkbase Document.		X
104	Cover Page Interactive Data File (formatted as inline XBRL and contained in Exhibit 101).		X

_________________________

# Indicates a management contract or compensatory plan.

* The certifications furnished in Exhibits 32.1 and 32.2 hereto are deemed to accompany this Form 10-Q and are not deemed “filed” for purposes of Section 18 of the Exchange Act, or otherwise subject to the liability of that section, nor shall they be deemed incorporated by reference into any filing under the Securities Act or the Exchange Act.

SIGNATURES

Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this Quarterly Report to be signed on its behalf by the undersigned thereunto duly authorized.

UPWORK INC.

Date: ~~October 26, 2022~~May 3, 2023

By:

/s/ Hayden Brown

Hayden Brown

President and Chief Executive Officer

~~(Principal Executive Officer)~~

~~Date: October 26, 2022~~

~~By:~~

~~/s/ Jeff McCombs~~

(Principal Executive Officer)

~~Jeff McCombs~~Date: May 3, 2023

By:

/s/ Erica Gessert

Erica Gessert

Chief Financial Officer

(Principal Financial Officer)

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