Our success depends on our ability to attract and retain top talent in a competitive marketplace, and to motivate that talent to achieve outstanding performance. Attracting, retaining, and motivating talented team members in key roles is especially critical at a time when we are seeking to transform our business, in particularWe have seen the Vista business where we have been investing heavily, including in hiring. Although we were already operating in a competitive marketcompetitiveness for talent we saw that competitiveness intensify during theover recent fiscal year,years and are often vying for qualified candidates against both larger, established companies with significant cash and equity resources and earlier-stage companies that can offer significant potential equity upside.

Since 2016, we have used performance share unit (PSU) awards asFiscal year 2023 was a key component oftransition year for our long-term incentive (LTI) compensation program for executives, employees, and directors. These PSU awards only pay out ifprogram. We continued the process that we began in fiscal year 2022 of moving away from performance share units with performance conditions based on the compound annual growth rate (CAGR) of the three-year moving average of the daily closing share price of Cimpress’ ordinary shares (3YMA), which we refer to as "3YMA-based PSUs." The 3YMA-based PSU awards pay out only if the 3YMA reaches or exceeds specified compound annual growth rate (CAGR) thresholds. In orderCAGR thresholds that require our 3YMA to reach those thresholds, the 3YMA must steadily increase over a period of several years. However, during both the initial phase of the pandemic and then again on a

As we entered fiscal year 2023, given the volatility of our share price and the expected impacts on our financial results of cost inflation and discretionary investments, the Compensation Committee decided to wait one year to put in place an entirely new performance-based LTI design. In fiscal year 2022,2023 our executives, other than Robert Keane, received a combination of (1) PSU awards that will pay out in four to eight years if the 3YMA CAGR thresholds are metshare options and (2) restricted share unit (RSU) awards that pay out, subject to continued employment through the applicable vesting date, in Cimpress ordinary shares over two to four years after grant. In light of the downward pressure on our 3YMA noted above and its impact on the retention and motivation value of PSU awards, and recognizing the elements of our PSU program design that were not effective in achieving their objective, we decided to stop granting PSU awards in their current form from and after fiscal year 2023, other than to Robert Keane. Instead, in fiscal year 2023, our executives, other than Mr. Keane, received a combination of (1) RSU awards that pay out, subject to continued employment through the applicable vesting date, in Cimpress ordinary shares over four years after grant and (2) share options that vest, subject to continued employment through the applicable vesting date, and become exercisable for Cimpress ordinary shares over four years after grant. We expect to continue to evaluate appropriate performance-based awards for future grants that are consistent with our objective of maximizing intrinsic value per share and are effective in retaining great talent.

Continuing the maximumevolution of our LTI compensation program after fiscal year 2023, the LTI awards granted to our executive officers in fiscal year 2024 consist solely of performance share units with performance targets based on the fiscal year 2024 revenue, adjusted EBITDA, and unlevered free cash flow of Cimpress (for Cimpress executive officers) or Vista (for Florian Baumgartner, our CEO of Vista). An important objective of this design is to move to a performance-based LTI mechanism that drives focus on in-year execution and achievement of our financial goals, while also incentivizing focus on long-term value creation and share price performance. After the end of fiscal year 2024, the number of PSUs we may grant him in any fiscal year is 75,000,shares issuable pursuant to each of these new performance share units will be determined and fixed based on the degree of achievement against these performance targets, and the performance thresholds in his PSU awards are thatshare units will vest over four years from the 3YMA CAGR must equal or exceed 11% over a performance perioddate of between six and ten years. In fiscal year 2022, Mr. Keane received 91% of his total compensation in the form of PSUs, including all of his Board retainer fees and LTI and most of his base salary.grant subject to continued employment on each vest date.

In determining the compensation of our executive officers, our Compensation Committee begins with an analysis of the competitiveness of our executive compensation program and, as a starting point, seeks to pay our executives base salary at the 50th percentile of the competitive market and total compensation (including base salary and target long-term incentive award values) at the 75th percentile of the competitive market. The Compensation Committee then applies its own discretion to take into account any other factors it may deem relevant in any given fiscal year, such as general economic conditions, the internal equity of compensation among our executives, each executive’s experience and role, and individual performance, and, particularly in fiscal years 2021 and 2022, the impact of the COVID-19 pandemic.performance. The Committee does not assign specific weights to particular factors but considers them together in determining compensation.

When considering the competitiveness of our executive compensation program for fiscal year 2022,2023, our Compensation Committee took into account a compensation analysis that we developed internally using data from the comparison peer group described below, published compensation survey data, and detailed historical compensation analyses for each executive officer. The Committee did not engage aan outside compensation consultant. We chose the 1816 publicly traded companies that comprise our peer group based on revenue, market capitalization, location, and industry, while taking into account the high-growth, technology-enabled businesses with which we might reasonably expect to compete for executive-level talent. The companies in our peer group for fiscal year 20222023 are:

The amount of total compensation granted to Mr. Keane's compensation remained the sameKeane did not change from fiscal year 20212022 to fiscal year 2022 because2023. In fiscal year 2023, Mr. Keane received all of his LTI compensation in the Compensation Committee wantedform of 3YMA-based PSUs, but unlike past years when he elected to see the Vista business progress further alongalso receive his base salary and director retention fee wholly or partially in its transformation before increasing3YMA-based PSUs, 100% of his base salary and director retention fee were paid in cash in fiscal year 2023. For fiscal year 2023, Mr. Keane's compensation. UponLTI compensation reached the recommendation75,000 PSUs per fiscal year limit set forth in the 2016 PSU Limitation Agreement between Cimpress and Mr. Keane, due to the decline in our 3YMA which is used to determine the number of Mr. Keane,3YMA-based PSUs underlying each award.

For fiscal year 2022,2023, our Compensation Committee maintained the base salaries of all three of our executive officers at their fiscal year 20212022 levels. Beginning in the second half of fiscal year 2019, at his option,In recent years, Mr. Keane has chosenelected to take as much of his base salary and director fees as much as possible in 3YMA-based PSUs within the 75,000 PSU per fiscal year limit set forth in his PSU Limitation Agreement. InAgreement, but in fiscal year 2022, the 75,000 PSU limit was reached because of our reduced 3YMA, so we2023, his base salary and Board retention fee were paid Mr. Keane $766,468entirely in cash representing the amount ofbecause his LTI compensation payable to Mr. Keane that exceededreached the 75,000 PSU limit.

In fiscal year 2022,2023, the components of our long-term incentive compensation program for executive officers consistedwere as follows:

We transitioned our LTI program for executives and a mix of PSUs and RSUs for our other executives. We increased the use of RSUs for our executive officersemployees other than Mr. Keane in fiscal year 2022away from 3YMA-based PSUs to enhance our ability to retain and motivate talented executivesemployees in an intensely competitive market for talent and to help mitigate the greatly reduced retention and motivation value of the 3YMA-based PSU awards we granted in past years that are increasingly unlikely to pay out given the sustained downward pressure on our share price and 3YMA. Mr. Keane received 100% of his LTI compensation3YMA in the form of PSUs,recent years.

The Compensation Committee believes that all employees based in the same geographic location should have access to similar levels of health and welfare benefits, and therefore our executive officers are eligible for the same health and welfare benefits, including medical, dental, vision, and disability plans, group life and accidental death and disability insurance and other benefit plans, as those offered to other employees in their location.

U.S.-based employees may participate in a 401(k) plan that provides a company match of up to 50% on the first 6% of the participant’s eligible compensation that is contributed, subject to certain limits under the United States Internal Revenue Code of 1986, or US Tax Code, with company matching contributions vesting over a four-year period.

We also provide customary pension plans to our European employees.

In general, executives are not entitled to benefits that are not otherwise available to all other employees who work in the same geographic location. We also fromFrom time to time, we enter into arrangements with some of our named executive officers to reimburse them for living and relocation expenses relating to their work outside of their home countries and for tax preparation fees and associated tax gross-ups. You can find more information about thesegross-ups, but none of our executive officers were subject to any such arrangements in the Summary Compensation Table of this proxy statement.fiscal year 2023.

We have entered into executive retention agreements with all of our named executive officers. Under the executive retention agreements, if we terminate an executive officer’s employment other than for cause, death, or disability or the executive terminates his or her employment for good reason before a change in control of Cimpress or within one year after a change in control (as cause, disability, good reason, and change in control are defined in the agreements), then the executive is entitled to receive:

Both the executive retention agreements and our 3YMA-based PSU awards have change in control provisions. The executive retention agreements provide that uponif there is a change in control of Cimpress plc or if the executive officer’s employment is terminated within 180 days before a change in control of Cimpress plc (other than a termination by Cimpress for cause or a resignation by the executive without good reason), then effective upon the date of the change in control:

The equity plans and agreements that govern our 3YMA-based PSUs provide that upon a change in control, all PSUs that have satisfied the applicable service-based vesting conditions will be settled for Cimpress ordinary shares in accordance with the terms of the awards if the actual price paid per share to holders of Cimpress' securities in connection with the change in control equals or exceeds the minimum 3YMA CAGR thresholds set forth in the award agreements.

The RSU agreement that governs the RSU award Mr. Baumgartner received on January 1, 2021 to replace 88% of his salary over a resultfour-year period provides that if Cimpress terminates Mr. Baumgartner's employment without cause (as defined in the agreement), then the "pro rata portion" of compensation payments made to him, or benefits he obtained (including theunvested RSUs will accelerate and become vested, but there is no acceleration of equity awards), in connection withupon a change in ownership or controlcontrol. The "pro rata portion" of Cimpress, we are required to pay him an amount, referred to as a gross-up payment,unvested RSUs is equal to (x) the amountnumber of such excise tax plus any additional taxes attributable to such gross-up payment. However, if reducing Mr. Keane's compensation payments by up to $50,000RSUs that would eliminatehave vested on the requirement to pay an excise tax under Section 4999first vesting date that follows the end of the US Tax Code, then Cimpress hasfiscal quarter in which Mr. Baumgartner's separation date occurs multiplied by (y) the rightquotient of the number of calendar days from the beginning of the fiscal quarter to reduce the paymentseparation date divided by up to $50,000 to avoid triggering the excise tax and thus avoid providing gross-up payments to Mr. Keane.number of calendar days in such fiscal quarter.

The following table sets forth information onabout the potential payments to our named executive officers upon their termination or a change in control of Cimpress, assuming that a termination or change in control took place on June 30, 2022.2023.

Although the Compensation Committee makes the final decisions about executive compensation, the Committee also takes into account the views of our Chief Executive Officer, who makes initial recommendations with respect to the compensation of executive officers other than himself. Other employees of Cimpress also participate in the preparation of materials presented to or requested by the Compensation Committee for use and consideration at Compensation Committee meetings.

We have share ownership guidelines for all of our executive officers and members of our Board of Directors. The guidelines require our executive officers and directors to hold Cimpress equity, including ordinary shares they hold directly or indirectly, unvested RSUs, vested and unvested PSUs, and vested, unexercised, in-the-money share options, with a value, based on the two-year trailing average of the closing prices of Cimpress' ordinary shares on Nasdaq, equal to or greater than a multiple of the executive officer’s annual base salary or the director's annual retainer, as follows:

We give each executive officer and Board member four years from his or her initial appointment as a Cimpress executive officer or director to comply with the share ownership guidelines. As of June 30, 2022,2023, all executive officers and directors had satisfied their ownership guideline requirement with the exception of Dessislava Temperley, who has until September 15, 2025requirement.

The Compensation Committee has reviewed and discussed with management the Compensation Discussion and Analysis contained in this proxy statement. Based on the Compensation Committee’s review and discussions

Mr. Keane's fiscal year 20222023 annual total compensation was $8,133,820,$3,077,261, as reported in the Summary Compensation Table above, and the fiscal year 20222023 annual total compensation of our median compensated employee other than Mr. Keane was $31,615.$24,600. The ratio of the median employee's total compensation to Mr. Keane's total compensation is 1-to-257. $7,342,285 (90%) of Mr. Keane's total compensation for fiscal year 2022 was in the form of PSU awards that will pay out six to ten years after grant only if the 3YMA CAGR thresholds are met.1-to-125.

Because there were no changes to our employee population or employee compensation from fiscal year 2020 to fiscal year 2022 that significantly impacted our pay ratio disclosure, we used the same median employee this year as we did for 2020. For purposes of identifying theWe identified a new median compensated employee for fiscal year 2020,2023 using the same methodology that we have used in the past: we took into account base salary (for salaried employees) and wages paid (for hourly employees) during the fiscal year for all our employees as of May 1, 2020.2023. We annualized this compensation for employees who did not work the entire fiscal year, except for employees designated as seasonal or temporary. For employees whose cash compensation was temporarily reduced for the fourth quarter of 2020 and replaced with RSUs as part of the salary restructuring program we instituted in fiscal year 2020 in response to the COVID-19 pandemic, we included the RSUs as part of each employee's base salary and assumed that the RSUs granted to each employee had the same value as the amount by which such employee’s cash compensation was reduced.