DEF 14A of CIMPRESS plc, Oct 28, 2025

DEF 14A of CIMPRESS plc

Filed Oct 28, 2025 · FY20250001262976-25-000107

Open on EDGAR

  1. INFORMATION ABOUT OUR DIRECTORS AND EXECUTIVE OFFICERS

    INFORMATION ABOUT OUR DIRECTORS AND EXECUTIVE OFFICERS Our Board of Directors: The Board of Directors of Cimpress plc (which is also referred to in this proxy statement as our Board of Directors or our Board) consists of four independent, non-employee directors and Robert S. Keane, our Chief Executive Officer and Chairman, who serve for rotating terms of three years. Additional information about our directors is as follows:

  2. INFORMATION ABOUT OUR DIRECTORS AND EXECUTIVE OFFICERS

    | Name | Age | Board Position | Cimpress Director Since: | Current Term Expires at our Annual General Meeting in: | Independent Director | | Robert S. Keane | 62 | Chairman | January 1995 | 2025 | No | | Sophie A. Gasperment | 61 | Non-Employee Director | November 2016 | 2026 | Yes | | Dessislava Temperley | 52 | Non-Employee Director | September 2021 | 2027 | Yes | | Wayne Ting* | 41 | Non-Employee Director | May 2025 | 2027 | Yes | | Scott J. Vassalluzzo | 53 | Non-Employee Director | January 2015 | 2025 | Yes |

  3. INFORMATION ABOUT OUR DIRECTORS AND EXECUTIVE OFFICERS

    _____________ * Mr. Ting was appointed to our Board on May 27, 2025. ROBERT S. KEANE has served as our Chief Executive Officer and Chairman since he founded Cimpress in January 1995. From 1988 to 1994, Mr. Keane was an executive at Flex-Key Corporation, an original equipment manufacturer of keyboards, displays and retail kiosks used for desktop publishing. Since December 2019, Mr. Keane has also served on the Board of Directors of Astronics Corporation, a supplier to the aerospace industry. Mr. Keane brings to Cimpress' Board his experience growing Cimpress from inception in 1995 to $3.4 billion of revenue in our 2025 fiscal year and his knowledge of Cimpress' customer needs, business model and markets. SOPHIE A. GASPERMENT has served as Senior Advisor to Boston Consulting Group since November 2019, where she supports their Consumer and Digital Acceleration practices, and has also provided strategy consulting services to several clients. Ms. Gasperment held multiple senior management positions during her tenure at L’Oréal from September 1986 to November 2018, including Managing Director, L’Oréal UK and Ireland as well as Chair and Global Chief Executive Officer of The Body Shop, the values-led retail brand that spanned 60 countries and was c.20,000 people strong during her tenure. Ms. Gasperment has served on the board of directors of Kingfisher plc, a FTSE 100 Home Improvement international company, since December 2018, and on the board of directors of Givaudan SA, a world leading flavour and fragrances company, since September 2020. Previously, Ms. Gasperment served for 12 years on the board of Accor from 2010 to 2022, the hospitality global player, where she chaired the Nomination/Remuneration/CSR committee, and of D’Ieteren Group, from 2018 to 2023. From September 2019 to July 2022, Ms. Gasperment also served as an "expert in residence" at Station F for the start-up incubator of HEC Paris. Ms. Gasperment brings to Cimpress' Board her leadership and strategy acumen, her consumer brand-building and go-to-market expertise, her insights in digital business transformation and her experience on the boards of other international public companies. DESSISLAVA TEMPERLEY has served on the boards of directors of Coca-Cola Europacific Partners PLC, a British multinational bottling company, since May 2020 and Philip Morris International Inc., a leading international tobacco company, since December 2021 and served on the board of directors of Corbion N.V., a Dutch food and biochemicals company, from May 2021 to May 2025. Ms. Temperley previously served as Group Chief Financial Officer of Beiersdorf AG, a German multinational company that manufactures personal-care products and pressure-sensitive adhesives, from July 2018 through June 2021. Ms. Temperley spent 14 years at Nestlé, from April 2004 through June 2018, serving in various roles including Head of Investor Relations, CFO of Nestle Purina Petcare (EMENA), Head of Global Planning and Performance Monitoring, Controller, and Finance Director. Ms. Temperley brings to Cimpress' Board a wealth of financial and operating expertise from her over 20 years of experience in various finance leadership roles and service on boards of directors and audit committees at multinational companies. WAYNE TING has served as Chief Executive Officer of Neutron Holdings, Inc. d/b/a Lime, which describes itself as the world’s largest shared electric vehicle company, since May 2020, and was Lime’s Global Head of Operations & Strategy from October 2018 to May 2020. Prior to that, Mr. Ting held multiple senior management positions at Uber Technologies, Inc., a technology platform company, from May 2014 to October 2018, including Chief of Staff to the CEO from July 2017 to October 2018. Mr. Ting also served as a Senior Policy Advisor for the National Economic Council to The White House from May 2012 to May 2014, a Private Equity Associate for Bain Capital, a global private equity firm, from July 2008 to June 2010, and a Business Analyst for McKinsey & Company, a leading management consulting firm, from June 2006 to June 2008. In addition, Mr. Ting co-founded CampusNetwork.com, the first college-based social networking site, in 2003. Mr. Ting brings to Cimpress' Board his extensive leadership experience in high-growth technology companies, deep expertise in operations and strategy, and a strong background in public policy and entrepreneurship. SCOTT J. VASSALLUZZO is a Managing Member of Prescott General Partners LLC (PGP), an investment advisory firm that holds 14.6% of Cimpress' outstanding shares. PGP serves as the general partner of three private investment limited partnerships, including Prescott Associates L.P. (together, the Prescott Partnerships). Mr. Vassalluzzo joined the Prescott organization in 1998 and has served as a Managing Member of PGP since January 2012. Prior to 1998, Mr. Vassalluzzo worked in public accounting at Coopers & Lybrand (now PricewaterhouseCoopers LLP) and was a certified public accountant. Mr. Vassalluzzo has served on the boards of directors of Credit Acceptance Corporation, an auto finance company providing automobile loans and other related financial products, since March 2007 and World Acceptance Corporation, a personal installment loan company, since August 2011. Mr. Vassalluzzo brings to Cimpress' Board his advocacy for the priorities of long-termism and intrinsic value per share, his appreciation and understanding of the perspectives of our other long-term shareholders, and his experience on the boards and board committees of other publicly traded companies. Our Executive Officers:

  4. INFORMATION ABOUT OUR DIRECTORS AND EXECUTIVE OFFICERS

    | Name | Title | Age | Joined Cimpress | | Robert S. Keane | Founder, Chief Executive Officer of Cimpress, and Chairman | 62 | January 1995 | | Sean E. Quinn | Executive Vice President and Chief Financial Officer | 46 | October 2009 | | Florian Baumgartner | Executive Vice President and Chief Executive Officer of Vista | 47 | October 2019 | | Maarten Wensveen | Executive Vice President and Chief Technology and MCP Operations Officer | 45 | October 2011 |

  5. INFORMATION ABOUT OUR DIRECTORS AND EXECUTIVE OFFICERS

    ROBERT S. KEANE has served as our Chief Executive Officer and Chairman since he founded Cimpress in January 1995, and his biography is in the "Our Board of Directors" section above. SEAN E. QUINN has served as our Chief Financial Officer since October 2015 and as Executive Vice President since July 2016. Mr. Quinn previously served as Senior Vice President from October 2015 to July 2016, as Chief Accounting Officer from November 2014 to October 2015, and in various other financial roles of increasing responsibility from October 2009 to November 2014. Before joining Cimpress, Mr. Quinn was a certified public accountant with KPMG LLP from September 2001 to October 2009 in the firm’s Philadelphia, London, and Boston offices. Mr. Quinn also serves on the board of directors of Credit Acceptance Corporation, an auto finance company providing automobile loans and other related financial products. FLORIAN BAUMGARTNER has served as the Chief Executive Officer of Vista since February 2023 and as Executive Vice President since October 2019. Mr. Baumgartner previously served as Vista's Executive Vice President, Design & Service, from March 2022 to January 2023 and as President, International of Vista from October 2019 to February 2022. Before joining Cimpress, Mr. Baumgartner held various leadership roles at Amazon from October 2010 to September 2019 and was a strategy consultant at McKinsey & Company from January 2002 to September 2010. MAARTEN WENSVEEN has served as our Executive Vice President and Chief Technology Officer since February 2019 and as our Chief MCP Operations Officer since October 2025. Mr. Wensveen previously served as Senior Vice President from January 2017 to February 2019, as Vice President of Technology from February 2015 to January 2017, and in various other technology leadership roles at Cimpress from December 2011 to January 2015. Mr. Wensveen joined Cimpress in November 2011 when we acquired Albumprinter, where he had been the Head of Information Technology for approximately six years. Prior to Albumprinter, Mr. Wensveen was the founder of Quantes IT, an infrastructure and software services company that delivered automation solutions in a range of industries. There are no family relationships among any of Cimpress' directors and executive officers. No arrangements or understandings exist between any director and any other person pursuant to which such person is to be selected for appointment to our Board of Directors.

  6. Executive Overview

    Executive Overview 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. Competitiveness for talent remains intense, and we often vie 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. Our Board and executive team value and actively seek the views and insights of our shareholders. In determining our executive compensation policies and decisions for fiscal year 2025, our Compensation Committee considered the results of the most recent shareholder advisory vote on our executive compensation, or the “say-on-pay” vote, at our 2023 annual meeting held in December 2023. For fiscal year 2025, we granted to our executive officers the same type of long-term incentive (LTI) awards as for fiscal year 2024. The LTI awards for each of these fiscal years consisted solely of performance share units (PSUs) with performance targets based on the financial metrics of revenue, adjusted EBITDA, and unlevered adjusted free cash flow for the applicable fiscal year of Cimpress (for Cimpress executive officers) or Vista (for Florian Baumgartner). The design of these PSUs, which we refer to as FY25 PSUs or FY24 PSUs, as applicable, maintains focus on both in-year financial performance and, because the awards vest over four-year periods, multi-year share price appreciation. Our FY25 PSUs and FY24 PSUs reflect our transition away from prior PSUs 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. As discussed in our 2023 and 2024 proxy statements, although the pay-for-performance structure of our 3YMA-based PSUs worked to align executive and employee incentives with shareholder interests, it also meaningfully impaired the retention and motivation value of 3YMA-based PSUs for Cimpress' executives and employees. Throughout this proxy statement we refer to our FY25 PSUs, FY24 PSUs and 3YMA-based PSUs collectively as PSUs. As part of the design of our FY25 PSUs and FY24 PSUs, our Compensation Committee assigned relative weightings to the financial metrics. For the FY25 PSUs, our Compensation Committee approved the following weightings: •Revenue: 20% (increased from 10% for FY24 PSUs) •Adjusted EBITDA: 40% (decreased from 45% for FY24 PSUs) •Unlevered adjusted free cash flow: 40% (decreased from 45% for FY24 PSUs) After the end of the applicable fiscal year, we generally determine the number of shares issuable pursuant to each FY25 PSU or FY24 PSU based on (i) the relative weighting for each financial metric and (ii) the degree of achievement against the performance target for each financial metric. In May 2025, our Compensation Committee approved an amendment to the FY25 PSUs to implement a 60% minimum payout multiplier for the number of shares issuable pursuant to each FY25 PSU to balance the importance of performance-based equity while enhancing retention and motivation, subject to the Committee’s discretion to account for non-recurring items in determining the final number of shares issuable, and the determination for FY25 PSUs was made in accordance with that amendment, as described further below.

  7. Competitive Compensation Program

    Competitive Compensation Program In determining the compensation of our executive officers, our Compensation Committee takes into account the competitiveness of our executive compensation program, the internal equity of compensation among our executives, and each executive’s impact, criticality, and scope of role. The Committee does not assign specific weights to particular factors but considers them together in determining compensation. To assess the competitiveness of our executive compensation program for fiscal year 2025, our Compensation Committee used 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 an outside compensation consultant. In advance of fiscal year 2025, we conducted a thorough peer group review to identify companies within various guidepost ranges for revenue, market capitalization, and enterprise value that, like Cimpress: •Are strong brands operating in the small and medium-sized businesses (SMBs) enablement and/or consumer spaces •Leverage technology to disrupt traditional industries or business models •Serve millions of customers around the globe, often through marketplace or platform models •Are entrepreneurial, innovative, and customer-focused Based on that review, we substantially refreshed our peer group from fiscal year 2024 and selected the following 14 companies as our peer group for fiscal year 2025:

  8. Competitive Compensation Program

    | 4imprint Group plc | GoDaddy Inc. | Upwork, Inc. | | Angi Inc. | LegalZoom.com, Inc. | Wayfair Inc. | | Deluxe Corporation | Shutterstock, Inc. | Yelp, Inc. | | DropBox, Inc. | Squarespace, Inc. | Yeti Holdings, Inc. | | Etsy, Inc. | TripAdvisor, Inc. | |

  9. Competitive Compensation Program

    For fiscal year 2025, the principal elements of our compensation program for our named executive officers did not change from fiscal year 2024 and included base salary, LTI awards in the form of FY25 PSUs, and standard health and welfare benefits that are applicable to employees in each executive's geographic location. Our Compensation Committee maintained the same base salary for each of our named executive officers from fiscal year 2024 to fiscal year 2025 and increased the grant values of LTI awards for our named executive officers in a range from 9% to 12% from fiscal year 2024 to fiscal year 2025, which resulted in increases to their total target compensation. As noted above, LTI awards for fiscal year 2025 consisted solely of FY25 PSUs based on the financial performance of Cimpress on a consolidated basis (in the case of Messrs. Keane, Quinn, and Wensveen) and of the Vista business (in the case of Mr. Baumgartner). Mr. Baumgartner received approximately half of his base salary for fiscal year 2025 in cash because he had elected in December 2020 to reduce his base salary by 88% for a four-year period from January 1, 2021 to December 31, 2024 in exchange for an RSU award granted on January 1, 2021 with a value (based on Cimpress' then-current share price) equal to the cumulative salary reduction, which RSUs vested in 16 equal quarterly installments over a four-year period.

  10. Long-Term Incentive Program

    Long-Term Incentive Program In fiscal year 2025, 100% of the LTI compensation we granted to our executive officers was in the form of FY25 PSUs, consistent with our approach for grants of FY24 PSUs in fiscal year 2024. Our executive officers also hold legacy 3YMA-based PSUs granted to them in prior fiscal years, none of which have paid out because none of the performance conditions has been satisfied, and our executive officers other than Mr. Keane hold share options and RSU awards that were granted to them in prior years and continued to vest in fiscal year 2025. FY25 PSUs. The performance target, weighting, and multipliers for the degree of achievement against the performance target for each financial metric for the FY25 PSUs at the time of approval were as follows:

  11. Long-Term Incentive Program

    | Revenue* - Fiscal Year 2025 Performance Target: $3,540,262,654 for Cimpress; $1,848,749,994 for Vista Weighting: 20% | | | | | | Percentage Achievement | <95% (Below Threshold) | 95% (Threshold) | 100% (Target) | 105% or higher (Maximum) | | Multiplier | 0% | 60% | 100% | 160% | | Adjusted EBITDA* - Fiscal Year 2025 Performance Target: $506,994,004 for Cimpress; $417,072,101 for Vista Weighting: 40% | | | | | | Percentage Achievement | <90% (Below Threshold) | 90% (Threshold) | 100-103% (Target) | 110% or higher (Maximum) | | Multiplier | 0% | 60% | 100% | 160% | | Unlevered Adjusted Free Cash Flow* - Fiscal Year 2025 Performance Target: $332,190,015 for Cimpress; $345,341,510 for Vista Weighting: 40% | | | | | | Percentage Achievement | <90% (Below Threshold) | 90% (Threshold) | 100-103% (Target) | 110% or higher (Maximum) | | Multiplier | 0% | 60% | 100% | 160% |

  12. Long-Term Incentive Program

    * See Appendix A to this proxy statement for information regarding how the amounts for these non-GAAP financial measures were calculated from financial measures reported in our audited financial statements. This includes, for example, the removal of share-based compensation expense from the Vista reported segment EBITDA; therefore, these targets are not directly comparable to reported results. After the end of the fiscal year, our Compensation Committee generally determines the multiplier for each financial metric based on the degree of achievement against the applicable performance target, and using the relative weightings for the financial metrics, determines the number of shares issuable pursuant to the awards, which vest over a four-year period following the grant date subject to continued employment through the applicable vesting date. As noted above, in May 2025, our Compensation Committee approved an amendment to the FY25 PSUs to implement a 60% minimum payout multiplier for the number of shares issuable pursuant to each FY25 PSU to balance the importance of performance-based equity while enhancing retention and motivation, subject to the Committee’s discretion to account for non-recurring items in determining the final number of shares issuable. Share Options and Restricted Share Units. In fiscal years prior to fiscal year 2024, we granted share options and RSU awards to executives other than Mr. Keane that vest over four-year periods. The share options have a ten-year term and an exercise price equal to the closing price of Cimpress' shares on the Nasdaq Global Select Market on the grant date. Upon vesting each RSU is settled in ordinary shares of Cimpress plc on a one-to-one basis so long as Cimpress continues to employ the recipient on the vesting date. 3YMA-Based PSUs. The 3YMA-based PSU awards granted to our executive officers prior to fiscal year 2024 pay out only if the 3YMA reaches or exceeds specified CAGR thresholds which require our 3YMA to steadily increase over a period of several years. The 3YMA-based PSU awards have performance periods ranging from four to ten years, and each anniversary of the grant date within the performance period is a performance measurement date. On the first such measurement date that the 3YMA equals or exceeds the threshold CAGR set forth in the award agreement as compared to the 3YMA at the date of grant, the performance condition would be satisfied, and we would issue to the employee the number of Cimpress ordinary shares determined by multiplying the number of PSUs subject to the award by the applicable performance-based multiplier. The performance-based multipliers range from 75% for a 7% 3YMA CAGR to 250% for a 3YMA CAGR of 20% or above. If the 3YMA CAGR does not reach at least the lowest performance threshold set forth in the PSU award agreement on any of the measurement dates during the performance period, then the PSU award terminates and no Cimpress ordinary shares would be issued with respect to the award. The 3YMA-based PSUs generally service vest 25% per year over four years so long as the employee remains employed by Cimpress on each vesting date. To date, no shares have been issued on any of the performance measurement dates for our outstanding 3YMA-based PSUs because our 3YMA has been below the applicable CAGR thresholds. The 3YMA CAGR thresholds are higher for future measurement dates, making future share issuances unlikely unless there is a dramatic and sustained increase in our share price.

  13. Realized Compensation

    Realized Compensation To supplement the Summary Compensation Table and other SEC-required tables and disclosure, the table immediately below presents, for each named executive officer, Realized Compensation as compared to the total from the Summary Compensation Table, where "Realized Compensation" means the total of (1) salary received (same as shown in Summary Compensation Table), (2) bonus received (same as shown in Summary Compensation Table), (3) the value of Cimpress shares issued pursuant to vesting of share awards, including shares withheld for taxes, and (4) the value (net of the exercise price) of Cimpress shares that became issuable upon exercise pursuant to vesting of option shares, in each case, during a given fiscal year. Because the Summary Compensation Table includes the value of equity awards only in the fiscal year during which they are granted and does not account for vesting of outstanding awards, the impacts of performance-based multipliers on vesting quantities, or changes to the price of Cimpress shares at the time of vesting events, an executive's Realized Compensation often varies significantly from the amounts shown in the Summary Compensation Table.

  14. Summary Compensation Table

    Summary Compensation Table The following table summarizes the compensation as required to be disclosed by SEC rules in each of the last three fiscal years for each of the following individuals, and we refer to them throughout this proxy statement as our named executive officers: (i) our principal executive officer, (ii) our principal financial officer, and (iii) our two other executive officers as of June 30, 2025.

  15. Summary Compensation Table

    | Name and Principal Position | Fiscal Year | Salary ($) | Bonus ($)(1) | Share Awards ($)(2)(3) | Option Awards ($)(2) | All Other Compensation ($) | Total ($) | | Robert S. Keane | 2025 | 1,000,000 | — | 9,838,993 | — | 10,454(4) | 10,849,447 | | Chairman and Chief | 2024 | 1,000,000 | — | 7,249,901 | — | 34,838 | 8,284,739 | | Executive Officer, Cimpress | 2023 | 1,756,346 | — | 1,320,915 | — | — | 3,077,261 | | Sean E. Quinn | 2025 | 800,000 | — | 4,673,524 | — | 10,500(5) | 5,484,024 | | Executive Vice President | 2024 | 800,000 | — | 3,399,997 | — | 10,096 | 4,210,093 | | and Chief Financial Officer | 2023 | 800,000 | — | 1,699,975 | 1,699,987 | 9,765 | 4,209,727 | | Florian Baumgartner(6) | 2025 | 404,306 | — | 2,999,970 | — | — | 3,404,276 | | Executive Vice President and | 2024 | 93,662 | 200,000 | 2,749,945 | — | — | 3,043,607 | | Chief Executive Officer, Vista | 2023 | 94,292 | 200,000 | 1,749,969 | 1,249,983 | — | 3,294,244 | | Maarten Wensveen | 2025 | 750,000 | — | 3,689,628 | — | 10,500(5) | 4,450,128 | | Executive Vice President and | 2024 | 750,000 | — | 2,749,945 | — | 10,350 | 3,510,295 | | Chief Technology Officer | 2023 | 750,000 | — | 1,374,958 | 1,374,988 | 10,350 | 3,510,296 |

  16. Summary Compensation Table

    | (1) Amounts reported are cash retention bonuses granted in prior fiscal years that vested and were paid in the fiscal years shown. | | (2) Amounts reported are grant date fair values of share awards and option awards as computed in accordance with FASB ASC Topic 718, using assumptions included in Note 10 to our audited financial statements in our Annual Report on Form 10-K for the fiscal year ended June 30, 2025, except to the extent described in footnote 3 to this table with respect to FY25 PSUs granted in fiscal year 2025. See footnote 5 to the Grants of Plan-Based Awards in the Fiscal Year Ended June 30, 2025 table for the value of the FY25 PSUs granted in fiscal year 2025 assuming the maximum achievement of the performance conditions. | | (3) Amounts reported for fiscal year 2025 also include the incremental fair value associated with implementing a 60% minimum payout multiplier for the number of shares issuable pursuant to the FY25 PSUs, subject to the Compensation Committee’s discretion to account for non-recurring items in determining the final number of shares issuable. The incremental fair value of these modifications for the named executive officers is $1,839,074 for Mr. Keane; $0 for Mr. Baumgartner; $873,528 for Mr. Quinn; and $689,658 for Mr. Wensveen. | | (4) Consists of (a) a $8,654 payout to prevent the loss of certain accrued time under the company's paid time off health and welfare benefit plans in connection with the transition to a new subsidiary serving as Mr. Keane's primary employer as a result of his relocation of his primary residence and principal work location and (b) the $1,800 cost the company incurred for Irish tax return preparation fees in respect of Mr. Keane's compensation as a director of Cimpress plc, which the company bears on behalf of each of the directors. | | (5) Amounts reported are matching contributions under our 401(k) deferred savings retirement plans. | | (6) Amounts reported, other than for share awards and option awards, were paid in Euros but are presented in U.S. Dollars, using for fiscal year 2025 amounts a conversion rate of €1.00 to $1.15187 based on the average currency exchange rate for the month of June 2025. |

  17. Grants of Plan-Based Awards in the Fiscal Year Ended June 30, 2025

    Grants of Plan-Based Awards in the Fiscal Year Ended June 30, 2025 The following table contains information about plan-based awards granted to each of our named executive officers during the fiscal year ended June 30, 2025.

  18. Grants of Plan-Based Awards in the Fiscal Year Ended June 30, 2025

    | | | Estimated Possible Payouts Under Equity Incentive Plan Awards(1) | | | Grant Date Fair Value of Share Awards | | | | Threshold | Target | Maximum | | | Name | Grant Date | (#)(2) | (#)(3) | (#)(4) | ($)(5)(6) | | Robert S. Keane | 8/15/2024 | 54,204 | 90,340 | 144,544 | 7,799,956 | | | 8/15/2024 | 1,390 | 2,316 | 3,706 | 199,963 | | | 5/23/2025 | — | — | — | 1,793,086 | | | 5/23/2025 | — | — | — | 45,988 | | Sean E. Quinn | 8/15/2024 | 26,407 | 44,012 | 70,419 | 3,799,996 | | | 5/23/2025 | — | — | — | 873,528 | | Florian Baumgartner | 8/15/2024 | 20,848 | 34,746 | 55,594 | 2,999,970 | | | 5/23/2025 | — | — | — | — | | Maarten Wensveen | 8/15/2024 | 20,848 | 34,746 | 55,594 | 2,999,970 | | | 5/23/2025 | — | — | — | 689,658 |

  19. Grants of Plan-Based Awards in the Fiscal Year Ended June 30, 2025

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  20. Grants of Plan-Based Awards in the Fiscal Year Ended June 30, 2025

    | (1) Share amounts reported are for FY25 PSU awards under which each PSU represents a right to receive between 0.6 and 1.6 Cimpress ordinary shares upon the satisfaction of (a) performance conditions relating to fiscal year 2025 revenue, adjusted EBITDA, and unlevered adjusted free cash flow of Cimpress (for Cimpress executive officers) or Vista (for Florian Baumgartner) and (b) service-based vesting, with vesting as to 25% of the earned PSUs on August 15, 2025 and as to 6.25% of the earned PSUs every three months thereafter until August 15, 2028. As noted in the Compensation Discussion and Analysis section, the FY25 PSUs were amended in May 2025 to implement a 60% minimum payout muliplier for the number of shares issuable pursuant to each FY25 PSU, subject to the Compensation Committee’s discretion to account for non-recurring items in determining the final number of shares issuable. | | (2) Reflects the number of shares subject to the award at 95% achievement against the revenue target and 90% achievement against the adjusted EBITDA and unlevered adjusted free cash flow targets (weighted multiplier of 60%). | | (3) Reflects the number of shares subject to the award at 100% achievement against the revenue, adjusted EBITDA, and unlevered adjusted free cash flow targets (weighted multiplier of 100%). | | (4) Reflects the number of shares subject to the award at 105% or above achievement against the revenue target and 110% or above achievement against the adjusted EBITDA and unlevered adjusted free cash flow targets (weighted multiplier of 160%). | | (5) Amounts reported for the 8/15/2024 grant date are grant date fair values of the awards as computed in accordance with FASB ASC Topic 718, using assumptions included in Note 10 to our audited financial statements in our Annual Report on Form 10-K for the fiscal year ended June 30, 2025. The maximum value of the awards assuming maximum achievement of the performance conditions is $12,799,819 for Mr. Keane, $4,799,900 for Messrs. Baumgartner and Wensveen, and $6,079,976 for Mr. Quinn, calculated by multiplying the maximum number of shares issuable pursuant to the applicable award by the closing price of Cimpress ordinary shares on Nasdaq on the grant date. | | (6) Amounts reported for the 5/23/2025 grant date are incremental fair values associated with modification of FY25 PSU awards to implement a 60% minimum payout multiplier, subject to the Compensation Committee’s discretion to account for non-recurring items in determining the final number of shares issuable. |

  21. Outstanding Equity Awards at June 30, 2025

    Outstanding Equity Awards at June 30, 2025 The following table contains information about outstanding equity awards as of June 30, 2025 for each of our named executive officers.

  22. Outstanding Equity Awards at June 30, 2025

    | | Option Awards | | | | Share Awards | | | | | | Number of Securities Underlying Unexercised Options (1) | | Option Exercise Price | Option Expiration Date | Number of Share Units That Have Not Vested | Market Value of Share Units That Have Not Vested | Equity Incentive Plan Awards: Number of Unearned Shares | Equity Incentive Plan Awards: Market Value of Unearned Shares | | Name | (#) Exercisable | (#) Unexercisable | ($) | | (#)(2) | ($)(3) | (#)(4) | ($)(5) | | Robert S. Keane | | | | | 87,515(6) | 4,113,205 | 93,750(8) | 4,406,250 | | | | | | | 55,594(7) | 2,612,918 | 78,970(9) | 3,711,590 | | | | | | | | | 73,498(10) | 3,454,406 | | | | | | | | | 10,759(11) | 505,673 | | | | | | | | | 91,536(12) | 4,302,192 | | | | | | | | | 1,398(13) | 65,706 | | | | | | | | | 19,010(14) | 893,470 | | | | | | | | | 1,403(15) | 65,941 | | | | | | | | | 73,335(16) | 3,446,745 | | | | | | | | | 79,322(17) | 3,728,134 | | | | | | | | | 10,886(17) | 511,642 | | | | | | | | | 1,611(18) | 75,717 | | | | | | | | | 1,288(19) | 60,536 | | | | | | | | | 91,768(20) | 4,313,096 | | | | | | | | | 1,981(21) | 93,107 | | Sean E. Quinn | 55,649 | 18,549 | 46.20 | 8/15/2032 | 41,136(6) | 1,933,392 | 24,301(8) | 1,142,147 | | | | | | | 26,407(7) | 1,241,129 | 20,306(9) | 954,382 | | | | | | | 2,804(22) | 131,788 | 18,898(10) | 888,206 | | | | | | | 11,498(23) | 540,406 | 22,952(24) | 1,078,744 | | | | | | | | | 19,641(25) | 923,127 | | | | | | | | | 19,410(26) | 912,270 | | Florian Baumgartner | 17,049 | 13,639 | 46.20 | 8/15/2032 | 31,950(6) | 1,501,650 | 10,743(29) | 504,921 | | | | | | | 20,848(7) | 979,856 | 10,999(25) | 516,953 | | | | | | | 934(22) | 43,898 | 10,451(26) | 491,197 | | | | | | | 8,263(27) | 388,361 | | | | | | | | | 8,455(23) | 397,385 | | | | | | | | | 7,179(28) | 337,413 | | | | Maarten Wensveen | 45,010 | 15,003 | 46.20 | 8/15/2032 | 33,272(6) | 1,563,784 | 14,400(8) | 676,800 | | | | | | | 20,848(7) | 979,856 | 6,016(9) | 282,752 | | | | | | | 2,337(22) | 109,839 | 3,651(10) | 171,597 | | | | | | | 9,300(23) | 437,100 | 18,362(24) | 863,014 | | | | | | | | | 20,951(25) | 984,697 | | | | | | | | | 16,175(26) | 760,225 |

  23. Outstanding Equity Awards at June 30, 2025

    ___________________

  24. Outstanding Equity Awards at June 30, 2025

    | (1) Each option award vests as to 25% of the original number of Cimpress ordinary shares subject to the award on June 30, 2023 and 6.25% of such number every three months thereafter until June 30, 2026, so long as the executive continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan through the applicable vesting date. |

  25. Outstanding Equity Awards at June 30, 2025

    | (2) Amounts reported are the number of Cimpress ordinary shares issuable upon vesting of RSU, FY24 PSU, or FY25 PSU awards. | | (3) Determined by multiplying the number of shares issuable upon vesting of each award by $47.00 per share (the closing price of Cimpress ordinary shares on Nasdaq on June 30, 2025). | | (4) Amounts reported are the number of Cimpress ordinary shares issuable pursuant to 3YMA-based PSU awards if the 3YMA CAGR condition described in the applicable footnote below for such award is satisfied (namely, achievement on any specified date within a specified timeframe of a specified 3YMA CAGR range relative to a specified share price, which in each case is the 3YMA of Cimpress ordinary shares on the award grant date, except for one award as noted below). No shares will be earned or issuable pursuant to a 3YMA-based PSU award unless and until the 3YMA on a measurement date meets or exceeds the CAGR performance threshold applicable for such award and service-based vesting occurs. Except as described in the applicable footnote below for a 3YMA-based PSU award, service-based vesting has been fully satisfied for such award. | | (5) Determined by multiplying the number of shares issuable pursuant to each 3YMA-based PSU award if the conditions described in the applicable footnote below for such award were achieved by $47.00 per share (the closing price of Cimpress ordinary shares on Nasdaq on June 30, 2025). | | (6) Reflects the number of shares earned pursuant to an FY24 PSU award (based on achievement against fiscal year 2024 revenue, adjusted EBITDA, and unlevered adjusted free cash flow performance targets) and issuable upon satisfaction of service-based vesting, with vesting as to 25% of the number of PSUs earned on August 15, 2024 and as to 6.25% of such number every three months thereafter until August 15, 2027. | | (7) Reflects the number of shares earned pursuant to an FY25 PSU award (based on achievement against fiscal year 2025 revenue, adjusted EBITDA, and unlevered adjusted free cash flow performance targets) and issuable upon satisfaction of service-based vesting, with vesting as to 25% of the number of PSUs earned on August 15, 2025 and as to 6.25% of such number every three months thereafter until August 15, 2028. | | (8) Reflects the number of shares issuable if the 3YMA CAGR is 11% to 11.99% on any August 15 of 2022 through 2026, compared to $69.44. | | (9) Reflects the number of shares issuable if the 3YMA CAGR is 11% to 11.99% on any August 15 of 2023 through 2027, compared to $83.10. | | (10) Reflects the number of shares issuable if the 3YMA CAGR is 11% to 11.99% on any August 15 of 2024 through 2028, compared to $102.68. | | (11) Reflects the number of shares issuable if the 3YMA CAGR is 11% to 11.99% on any February 15 of 2025 through 2029, compared to $109.35. | | (12) Reflects the number of shares issuable if the 3YMA CAGR is 11% to 11.99% on any August 15 of 2025 through 2029, compared to $108.92. | | (13) Reflects the number of shares issuable if the 3YMA CAGR is 11% to 11.99% on any November 15 of 2025 through 2029, compared to $111.70. | | (14) Reflects the number of shares issuable if the 3YMA CAGR is 11% to 11.99% on any August 15 of 2026 through 2030, compared to $112.72. | | (15) Reflects the number of shares issuable if the 3YMA CAGR is 11% to 11.99% on any November 15 of 2026 through 2030, compared to $111.23. | | (16) Reflects the number of shares issuable if the 3YMA CAGR is 11% to 11.99% on any February 15 of 2027 through 2031, compared to $108.31. | | (17) Reflects the number of shares issuable if the 3YMA CAGR is 11% to 11.99% on any August 15 of 2027 through 2031, compared to $100.46. | | (18) Reflects the number of shares issuable if the 3YMA CAGR is 11% to 11.99% on any November 15 of 2027 through 2031, compared to $96.94, with service-based vesting as to 25% of the PSUs on November 29 of each of 2022 through 2025 so long as Mr. Keane continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan through such vesting date. | | (19) Reflects the number of shares issuable if the 3YMA CAGR is 11% to 11.99% on any November 15 of 2027 through 2031, compared to $96.94. | | (20) Reflects the number of shares issuable if the 3YMA CAGR is 11% to 11.99% on any November 16 of 2028 through 2032, compared to $78.82, with service-based vesting as to 25% of the PSUs on June 30 of each of 2023 through 2026 so long as Mr. Keane continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan through such vesting date. | | (21) Reflects the number of shares issuable if the 3YMA CAGR is 11% to 11.99% on any November 16 of 2028 through 2032, compared to $78.82, with service-based vesting as to 25% of the PSUs on November 15 of each of 2023 through 2026 so long as Mr. Keane continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan through such vesting date. | | (22) This RSU award vests as to 25% of the original number of units on August 15 of each of 2022 through 2025, on each of which dates we will automatically issue one ordinary share for each vested unit so long as the executive continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan through that date. | | (23) This RSU award vests as to 25% of the original number of units on August 15, 2023 and as to an additional 6.25% on the 15th day of every third month thereafter until August 15, 2026, on each of which dates we will automatically issue one ordinary share for each vested unit so long as the executive continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan through that date. |

  26. Outstanding Equity Awards at June 30, 2025

    | (24) Reflects the number of shares issuable if the 3YMA CAGR is 9% to 9.99% on any August 15 of 2023 through 2027, compared to $108.92. | | (25) Reflects the number of shares issuable if the 3YMA CAGR is 9% to 9.99% on any February 15 of 2025 through 2029, compared to $95.46, which was the two-year moving average daily closing price of Cimpress ordinary shares on the grant date. | | (26) Reflects the number of shares issuable if the 3YMA CAGR is 9% to 9.99% on any August 15 of 2025 through 2029, compared to $100.46. | | (27) This RSU award vests as to 25% of the original number of units on April 15 of each of 2023 through 2026, on each of which dates we will automatically issue one ordinary share for each vested unit so long as Mr. Baumgartner continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan through that date. | | (28) This RSU award vests as to 25% of the original number of units on January 15, 2024 and as to an additional 6.25% on the 15th day of every third month thereafter until January 15, 2027, on each of which dates we will automatically issue one ordinary share for each vested unit so long as Mr. Baumgartner continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan through that date. | | (29) Reflects the number of shares issuable if the 3YMA CAGR is 9% to 9.99% on any November 15 of 2023 through 2027, compared to $111.70. |

  27. CEO Pay Ratio

    CEO Pay Ratio Mr. Keane's fiscal year 2025 annual total compensation was $10,849,447, as reported in the Summary Compensation Table above, and the fiscal year 2025 annual total compensation of our median compensated employee other than Mr. Keane was $30,145. The ratio of the median employee's total compensation to Mr. Keane's total compensation is 1-to-360. As supplemental information, Mr. Keane's Realized Compensation for fiscal year 2025, as described above in the Compensation Discussion and Analysis section, was $6,071,552, which yields a ratio of 1-to-201. For the median employee for fiscal year 2025, because the employment of the median employee for fiscal year 2023 ended during fiscal year 2025, we used a replacement employee from the median grouping we had established for fiscal year 2023 whose compensation was substantially similar to the original median employee for fiscal year 2023. In addition, there were no changes to our employee population or employee compensation from fiscal year 2023 to fiscal year 2025 that significantly impacted our pay ratio disclosure. For purposes of identifying the median compensated employee for fiscal year 2023, we used 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 in all countries as of May 1, 2023. We annualized this compensation for employees who did not work the entire fiscal year, except for employees designated as seasonal or temporary.

  28. PAY VERSUS PERFORMANCE

    PAY VERSUS PERFORMANCE The following table sets forth the total compensation of Robert Keane, our Chief Executive Officer (who is our principal executive officer as defined by SEC rules) and the average total compensation of our other named executive officers (Other NEOs) for fiscal years 2025, 2024, 2023, 2022, and 2021, both as reported in the Summary Compensation Table and with certain adjustments to reflect the “compensation actually paid” to such individuals, calculated in accordance with applicable SEC rules. Our Compensation Committee did not consider “compensation actually paid,” as defined by SEC rules, when making its executive compensation decisions for the covered fiscal years, and “compensation actually paid” does not reflect amounts actually realized or realizable by our CEO and Other NEOs and may be higher or lower than the amounts our executives actually realize. Please see the Compensation Discussion and Analysis section in this proxy statement for a discussion of our Compensation Committee’s philosophy, objectives, and practices when making executive compensation decisions, as well as a discussion of "Realized Compensation," including a calculation of compensation realized or realizable by our executives in each fiscal year.

  29. Pay Versus Performance Table

    Pay Versus Performance Table

  30. Pay Versus Performance Table

    | Year | Summary Compensation Table Total for CEO ($) | Compensation Actually Paid to CEO ($)(1) | Average Summary Compensation Table Total for Other NEOs ($) | Average Compensation Actually Paid to Other NEOs ($)(2) | Value of Initial Fixed $100 Investment Based On: | | Cimpress' Net Income (Loss) (in thousands) ($)(4) | Cimpress' Adjusted EBITDA (in thousands) ($)(5) | | | | | | | Cimpress Total Shareholder Return ($)(3) | Peer Group Total Shareholder Return ($)(3) | | | | 2025 | 10,849,447 | (20,054,856) | 4,446,143 | (2,877,241) | 61.57 | 142.42 | 14,952 | 433,167 | | 2024 | 8,284,739 | 21,341,751 | 3,587,998 | 8,308,863 | 114.76 | 123.66 | 173,682 | 468,682 | | 2023 | 3,077,261 | 15,721,823 | 3,671,422 | 7,673,690 | 77.91 | 91.24 | (185,978) | 339,832 | | 2022 | 8,133,820 | (30,575,430) | 6,310,409 | (5,800,169) | 50.96 | 82.38 | (54,331) | 281,063 | | 2021 | 8,340,034 | 18,254,681 | 5,320,963 | 7,884,721 | 142.01 | 130.30 | (85,229) | 349,118 |

  31. Pay Versus Performance Table

    _____________ (1) Mr. Keane served as our principal executive officer for each of fiscal years 2021 through 2025. The following table shows for each covered fiscal year the adjustments made to the total compensation shown for Mr. Keane in the Summary Compensation Table to arrive at "compensation actually paid" as reflected in the table above.

  32. Pay Versus Performance Table

    | Adjustments to Determine CEO Compensation Actually Paid | 2025 | 2024 | 2023 | 2022 | 2021 | | Summary Compensation Table Total | 10,849,447 | 8,284,739 | 3,077,261 | 8,133,820 | 8,340,034 | | Subtract: Grant date fair values of equity awards reported in "Stock Awards" column of the Summary Compensation Table | (9,838,993) | (7,249,901) | (1,320,915) | (7,342,285) | (8,283,797) | | Add: Fair value as of the end of the covered fiscal year (FY) of all equity awards granted during the covered FY that remain outstanding and unvested as of the end of the FY | 4,354,832 | 9,027,159 | 4,870,500 | 1,508,362 | 8,752,710 | | Add: The change in fair value (whether positive or negative) as of the end of the covered FY from the end of the prior FY of any equity awards granted in any prior FY that remain outstanding and unvested as of the end of the covered FY | (26,542,323) | 11,279,754 | 9,094,977 | (32,875,327) | 9,445,734 | | Add: The fair value as of the vesting date of any equity awards that are granted and vest in the same FY | — | — | — | — | — | | Add: The change in fair value (whether positive or negative) as of the vesting date from the end of the prior FY of any equity awards granted in any prior FY for which all applicable vesting conditions were satisfied at the end of or during the covered FY | 1,122,181 | — | — | — | — | | Subtract: Fair value at the end of the prior FY of any equity awards that fail to meet the applicable vesting conditions during the covered FY | — | — | — | — | — | | Compensation Actually Paid to CEO | (20,054,856) | 21,341,751 | 15,721,823 | (30,575,430) | 18,254,681 |

  33. Pay Versus Performance Table

    (2) The Other NEOs whose compensation amounts are averaged and included in this table are Sean Quinn and Maarten Wensveen for all five fiscal years and Florian Baumgartner for fiscal years 2023 through 2025. The following table shows for each covered fiscal year the adjustments made to the average of the total compensation shown for the Other NEOs in the Summary Compensation Table to arrive at "compensation actually paid" as reflected in the table above.

  34. Pay Versus Performance Table

    | Adjustments to Determine Average Other NEO Compensation Actually Paid | 2025 | 2024 | 2023 | 2022 | 2021 | | Summary Compensation Table Total (Average) | 4,446,143 | 3,587,998 | 3,671,422 | 6,310,409 | 5,320,963 | | Subtract: Grant date fair values of equity awards reported in "Option Awards" column of the Summary Compensation Table | — | — | (1,441,653) | — | — | | Subtract: Grant date fair values of equity awards reported in "Stock Awards" column of the Summary Compensation Table | (3,787,707) | (2,966,629) | (1,608,301) | (5,461,685) | (4,349,908) | | Add: Fair value as of the end of the covered fiscal year (FY) of all equity awards granted during the covered FY that remain outstanding and unvested as of the end of the FY | 1,778,229 | 3,702,369 | 3,860,753 | 1,965,020 | 5,010,937 | | Add: The change in fair value (whether positive or negative) as of the end of the covered FY from the end of the prior FY of any equity awards granted in any prior FY that remain outstanding and unvested as of the end of the covered FY | (4,840,150) | 2,938,491 | 2,603,464 | (8,604,847) | 1,867,160 | | Add: The fair value as of the vesting date of any equity awards that are granted and vest in the same FY | — | — | 559,795 | — | — | | Add: The change in fair value (whether positive or negative) as of the vesting date from the end of the prior FY of any equity awards granted in any prior FY for which all applicable vesting conditions were satisfied at the end of or during the covered FY | (473,756) | 1,046,634 | 28,210 | (9,066) | 35,569 | | Subtract: Fair value at the end of the prior FY of any equity awards that fail to meet the applicable vesting conditions during the covered FY | — | — | — | — | — | | Average Compensation Actually Paid to Other NEOs | (2,877,241) | 8,308,863 | 7,673,690 | (5,800,169) | 7,884,721 |

  35. Pay Versus Performance Table

    (3) Our peer group for purposes of this table is the Research Data Group (RDG) Internet Composite Index, which is the published industry index included in the performance graph in our Annual Report on Form 10-K for all five of the covered fiscal years. The cumulative total shareholder returns for Cimpress ordinary shares and the RDG Internet Composite index are calculated by assuming an investment on June 30, 2020 of $100 (with reinvestment of all dividends) in our ordinary shares and in the index. (4) Reflects Cimpress' net income (loss) in the audited financial statements published in our Annual Report on Form 10-K for the applicable year. (5) One of three financial metrics included in FY24 PSU and FY25 PSU awards granted to our executive officers was the actual adjusted EBITDA of Cimpress on a consolidated basis (for Messrs. Keane, Quinn, and Wensveen) and of the Vista business (for Mr. Baumgartner) compared to performance targets set by our Compensation Committee, as described in more detail in the Compensation Discussion and Analysis section of this proxy statement.

  36. Relationship between Compensation Actually Paid and Performance Metrics

    Relationship between Compensation Actually Paid and Performance Metrics The following graphs show the relationship between the amount of compensation actually paid to Mr. Keane and the average amount of compensation actually paid to the Other NEOs for each fiscal year and (i) the total shareholder return of Cimpress and its peer group calculated through the end of such fiscal year, (ii) Cimpress' net income (loss) for such fiscal year, and (iii) Cimpress' adjusted EBITDA for such fiscal year, in each case as set forth in the Pay Versus Performance Table above.

  37. Compensation Actually Paid vs. Cimpress TSR and Peer Group TSR

    Compensation Actually Paid vs. Cimpress TSR and Peer Group TSR

  38. Compensation Actually Paid vs. Cimpress Net Income (Loss)

    Compensation Actually Paid vs. Cimpress Net Income (Loss)

  39. Compensation Actually Paid vs. Cimpress Adjusted EBITDA

    Compensation Actually Paid vs. Cimpress Adjusted EBITDA

  40. Non-Employee Director Compensation Table

    Non-Employee Director Compensation Table The following table contains information about the compensation earned by our non-employee directors in the fiscal year ended June 30, 2025:

  41. Non-Employee Director Compensation Table

    | Name | Fees Earned or Paid in Cash ($) | Share Awards ($)(1) | Total ($) | | Sophie A. Gasperment | 100,000 | 199,947 | 299,947 | | Dessislava Temperley | 125,000 | 199,947 | 324,947 | | Wayne Ting(2) | 9,445 | 99,975 | 109,420 | | Scott J. Vassalluzzo | 100,000 | 199,947 | 299,947 | | Zachary S. Sternberg(3) | 50,000 | — | 50,000 |

  42. Non-Employee Director Compensation Table

    | (1) Amounts reported are grant date fair values of RSUs as computed in accordance with FASB ASC Topic 718, using assumptions included in Note 10 to our audited financial statements in our Annual Report on Form 10-K for the fiscal year ended June 30, 2025. | | (2) Mr. Ting was appointed as a director on May 27, 2025. | | (3) Mr. Sternberg's term as a director expired in November 2024. |

  43. Non-Employee Director Compensation Table

    In addition, at June 30, 2025, our non-employee directors held the following outstanding equity compensation awards:

  44. Non-Employee Director Compensation Table

    | • | Ms. Gasperment held 6,753 3YMA-based PSUs and 6,638 RSUs. | | • | Ms. Temperley held 7,073 RSUs. | | • | Mr. Ting held 2,325 RSUs. | | • | Mr. Vassalluzzo held 6,239 3YMA-based PSUs, 6,638 RSUs, and unexercised share options to purchase an aggregate of 1,309 shares. |