cmpr-20241009

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

WASHINGTON, DC 20549

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CIMPRESS PLC

First Floor Building 3, Finnabair Business and Technology Park

Dundalk, Co. Louth A91 XR61

Ireland

NOTICE OF ANNUAL GENERAL MEETING OF SHAREHOLDERS

Cimpress plc will hold its 2024 Annual General Meeting of Shareholders:

on Wednesday, November 20, 2024

at 6:00 p.m. Dublin Time

at the offices of Matheson LLP

70 Sir John Rogerson's Quay

Dublin 2, D02 R296

Ireland

MATTERS TO BE ACTED UPON AT THE ANNUAL GENERAL MEETING:

(1) Reappoint Dessislava Temperley to our Board of Directors to serve for a term of three years ending at the conclusion of our annual general meeting of shareholders in 2027

(2) Approve, on a non-binding, advisory basis, the compensation of our named executive officers, as described in this proxy statement

(3) Amend our 2020 Equity Incentive Plan to increase the number of ordinary shares issuable under the plan by 2,000,000 shares

(4) Renew the authority of our Board of Directors, until May 20, 2026, to issue authorized but unissued ordinary shares of Cimpress plc up to a maximum of 20% of our issued and outstanding share capital

(5) Renew the authority of our Board of Directors, until May 20, 2026, to opt out of statutory preemption rights under Irish law with respect to the issuance of ordinary shares for cash, up to a maximum of 20% of our issued and outstanding share capital

(6) Reappoint PricewaterhouseCoopers Ireland as our statutory auditor under Irish law to hold office until the conclusion of our annual general meeting of shareholders in 2025

(7) Authorize our Board of Directors or Audit Committee to determine the remuneration of PricewaterhouseCoopers Ireland in its capacity as our statutory auditor under Irish law

(8) Transact other business, if any, that may properly come before the meeting or any adjournment of the meeting

Each proposal other than Proposal 5 will be proposed as ordinary resolutions under Irish law, requiring, in each case, at least a simple majority of the votes cast to be in favor of the resolution for the resolution to pass. Proposal 5 will be proposed as a special resolution under Irish law, requiring at least 75% of the votes cast to be in favor of the resolution to pass.

During the annual general meeting, management will present, for consideration by the shareholders, our statutory financial statements under Irish law for the fiscal year ended June 30, 2024 (including the reports of the directors and the Irish statutory auditor thereon) and a review of Cimpress' affairs.

Our Board of Directors has no knowledge of any other business to be transacted at the annual general meeting.

Shareholders of record at the close of business on September 20, 2024 are entitled to attend and vote at the annual general meeting, or to appoint one or more proxies to attend, speak, and vote instead of the shareholder at the annual general meeting. A proxy need not be a shareholder. To be valid, a proxy must be received no later than

4:00 p.m. Eastern Standard Time on November 19, 2024 at one of the address(es) and otherwise in the manner described in the attached proxy statement. Your vote is important regardless of the number of shares you own. Whether or not you expect to attend the meeting, please complete and promptly return the proxy card or voter instruction form in accordance with the instructions that we or your bank or brokerage firm have provided. Your prompt response will ensure that your shares are represented at the annual general meeting. You can change your vote and revoke your proxy by following the procedures described in this proxy statement.

Please read the attached proxy statement for additional information on the matters to be considered at the annual general meeting. The proxy statement is incorporated into this notice by this reference.

All shareholders are cordially invited to attend the annual general meeting.

By order of the Board of Directors,

Robert S. Keane

Founder, Chairman and Chief Executive Officer

October 9, 2024

CIMPRESS PLC

First Floor Building 3, Finnabair Business and Technology Park

Dundalk, Co. Louth A91 XR61

Ireland

PROXY STATEMENT FOR ANNUAL GENERAL MEETING OF SHAREHOLDERS

to be held on November 20, 2024

This proxy statement contains information about the 2024 Annual General Meeting of Shareholders of Cimpress plc, which we refer to in this proxy statement as the annual meeting or the meeting. We will hold the annual meeting on Wednesday, November 20, 2024 at the offices of Matheson LLP, 70 Sir John Rogerson's Quay, Dublin 2, D02 R296, Ireland. The meeting will begin at 6:00 p.m. Dublin Time.

We are furnishing this proxy statement to you in connection with the solicitation of proxies by the Board of Directors of Cimpress plc (which is also referred to as we, us, the company, or Cimpress in this proxy statement) for use at the annual meeting and at any adjournment of the annual meeting.

We are first mailing or making available the Notice of Annual General Meeting, this proxy statement, and our Annual Report to Shareholders for the fiscal year ended June 30, 2024 on or about October 10, 2024.

Important Notice Regarding the Availability of Proxy Materials for the 2024 Annual General Meeting of Shareholders:

This Proxy Statement, the 2024 Annual Report to Shareholders, and the statutory financial statements under Irish law for the fiscal year ended June 30, 2024 (including the reports of our directors and our Irish statutory auditor thereon) are available for viewing, printing and downloading at http://www.viewproxy.com/Cimpress/2024. We will furnish without charge a copy of this proxy statement and our Annual Report on Form 10-K for the fiscal year ended June 30, 2024, as filed with the United States Securities and Exchange Commission, or SEC, as well as the statutory financial statements under Irish law for the fiscal year ended June 30, 2024 (including the reports of our directors and our Irish statutory auditor thereon), to any shareholder who requests it by emailing ir@cimpress.com or writing to Cimpress plc, c/o Cimpress USA Incorporated, Attention: Investor Relations, 275 Wyman Street, Waltham, MA 02451, USA. This proxy statement and our Annual Report on Form 10-K are also available on the SEC’s website at www.sec.gov.

For this annual meeting, we are taking advantage of the SEC rule allowing companies to furnish proxy materials to some or all of their shareholders over the Internet. We believe that this e-proxy process expedites shareholders' receipt of proxy materials, while lowering the costs and reducing the environmental impact of our annual meeting. On or about October 10, 2024 we are mailing to our beneficial shareholders a Notice of Internet Availability containing instructions on how to access our proxy statement and 2024 Annual Report to Shareholders and how to vote online. The Notice of Internet Availability contains instructions on how you can (i) receive a paper copy of the proxy statement, proxy card and Annual Report if you received only a Notice by mail or (ii) elect to receive your proxy statement and Annual Report over the Internet if you received them by mail this year. All shareholders other than beneficial holders will continue to receive a paper copy of this proxy statement, proxy card and Annual Report by mail.

TABLE OF CONTENTS


Section			Page Number
Information about our directors and executive officers			1
Proposal 1: Reappoint a member of our Board of Directors			4
Proposal 2: Advisory vote to approve executive compensation			4
Compensation Discussion and Analysis			4
Executive Compensation Tables			12
Pay Versus Performance			19
Proposal 3: Amendment of Equity Plan			24
Proposal 4: Authorize our Board of Directors to issue ordinary shares			32
Proposal 5: Authorize our Board to opt out of statutory preemptive rights			32
Proposal 6: Reappoint our statutory auditor			33
Proposal 7: Authorize our Board to determine remuneration of our statutory auditor			35
Corporate Governance			36
Compensation of our Board of Directors			42
Security ownership of certain beneficial owners and management			43
Questions and answers about the annual meeting and voting			45

Appendix A - Non-GAAP Reconciliations
Appendix B - 2020 Equity Incentive Plan as proposed to be amended
Appendix C - Form of Proxy

INFORMATION ABOUT OUR DIRECTORS AND EXECUTIVE OFFICERS

Our Board of Directors:

The Board of Directors of Cimpress plc consists of four independent, non-employee directors and Robert Keane, our Chief Executive Officer and Chairman, who serve for rotating terms of three years.

Name

Age

Board Position

Cimpress Director Since

Current Term Expires at our Annual General Meeting In:

Independent Director

Robert S. Keane

Chairman

January 1995

2025

Sophie A. Gasperment

Non-Employee Director

November 2016

2026

Yes

Zachary S. Sternberg*

Non-Employee Director

November 2017

2024

Yes

Dessislava Temperley

Non-Employee Director

September 2021

2024

Yes

Scott J. Vassalluzzo

Non-Employee Director

January 2015

2025

Yes

*Mr. Sternberg is not standing for re-election at the 2024 annual meeting.

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 nearly $3.3 billion of revenue in our 2024 fiscal year, his understanding of the drivers of our intrinsic value per share, 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. From September 2019 to July 2022, Ms. Gasperment served as an "expert in residence" at Station F for the start-up incubator of HEC Paris. 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 value-led retail brand spanning 60 countries and c.20,000 people strong. 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, the hospitality global player, where she chaired the Nomination/Remuneration/CSR committee, and of D’Ieteren Group. In addition to serving on the Board of Directors of Cimpress plc, Ms. Gasperment serves on the supervisory board of Vistaprint B.V., a wholly owned Dutch subsidiary of Cimpress. 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.

ZACHARY S. STERNBERG is the co-founder and Managing Member of the General Partner of The Spruce House Partnership, a New York-based investment partnership. Spruce House invests in public and private companies globally and seeks to partner with management teams that are focused on growing the per share value of their companies over the long-term. Spruce House holds 8.2% of Cimpress' outstanding shares and has been a shareholder of Cimpress since 2011. Mr. Sternberg brings to Cimpress' Board his perspective as a material and long-term shareholder of Cimpress with a deep understanding of the importance of long-term stewardship of capital informed by more than 15 years of successful investment experience.

DESSISLAVA TEMPERLEY serves on the boards of Coca-Cola Europacific Partners PLC, a British multinational bottling company; Corbion N.V., a Dutch food and biochemicals company; and Philip Morris International Inc., a leading international tobacco company. 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. In addition to serving on the Board of Directors of Cimpress plc, Ms. Temperley serves on the supervisory board of Vistaprint B.V., a wholly owned Dutch subsidiary of Cimpress. 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.

SCOTT J. VASSALLUZZO is a Managing Member of Prescott General Partners LLC (PGP), an investment advisory firm that holds 15.5% 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 serves on the boards of directors of Credit Acceptance Corporation, an auto finance company providing automobile loans and other related financial products, and World Acceptance Corporation, a personal installment loan company. 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.

Board Diversity Matrix as of June 30, 2024

We believe directors with diverse backgrounds, including gender diversity, provide competing perspectives that enhance the Board's effectiveness. The table below sets forth information on the voluntarily self-identified diversity characteristics of the members of our Board of Directors.


Total number of directors			5
Gender or Demographic Background			Number of Directors Who Self-Identify as Having That Gender or Demographic Background
Female			2
Male			3
White			4
Did not disclose demographic background			1

Non-U.S. directors			2

Our Executive Officers:


Name	Title	Age	Joined Cimpress
Robert S. Keane	Founder, Chief Executive Officer of Cimpress, and Chairman	61	January 1995
Florian Baumgartner	Executive Vice President and Chief Executive Officer of Vista	46	October 2019
Sean E. Quinn	Executive Vice President and Chief Financial Officer	45	October 2009
Maarten Wensveen	Executive Vice President and Chief Technology Officer	44	October 2011

ROBERT S. KEANE: Mr. Keane's biography is in the "Our Board of Directors" section above.

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.

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, as Vice President, Corporate Finance from January 2014 to October 2015, as Global Controller from April 2012 to November 2014, and in various other financial roles from October 2009 to April 2012. 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.

MAARTEN WENSVEEN has served as our Executive Vice President and Chief Technology Officer since February 2019. 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 the Board of Directors.

PROPOSAL 1 - REAPPOINT DESSISLAVA TEMPERLEY TO OUR BOARD OF DIRECTORS

The members of our Board of Directors serve for rotating terms of up to three years. In accordance with the recommendation of the Nominating Committee of the Board, our Board recommends the reappointment of Ms. Temperley for a three-year term ending at the conclusion of our annual general meeting of shareholders in 2027, because of her 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. You can find more information about Ms. Temperley in the section of this proxy statement entitled “INFORMATION ABOUT OUR DIRECTORS AND EXECUTIVE OFFICERS.”

Our Board of Directors recommends that you vote FOR the reappointment of Ms. Temperley to the Board.

PROPOSAL 2 - ADVISORY VOTE TO APPROVE EXECUTIVE COMPENSATION

At the annual meeting, in accordance with Section 14A of the U.S. Securities Exchange Act of 1934, we are asking our shareholders to approve the compensation of our named executive officers, as described in the Compensation Discussion and Analysis section, executive compensation tables, and accompanying narrative disclosures below. This is an advisory vote, meaning that this proposal is not binding on us, but our Compensation Committee takes shareholder feedback into account when designing our executive compensation program.

At our annual general meeting in 2023, a majority of our shareholders voted to hold the advisory vote to approve our executive compensation on an annual basis. Therefore, we intend to put forth at each annual general meeting of shareholders an advisory vote on the compensation of our named executive officers for the immediately preceding fiscal year.

Our Board of Directors recommends that you vote FOR the approval of the compensation of our named executive officers, as described below.

COMPENSATION DISCUSSION AND ANALYSIS

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. We have seen the competitiveness for talent intensify over recent 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.

In fiscal year 2024, we completed our transition away from granting 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. As discussed in our 2023 proxy statement, while the pay-for-performance structure of our 3YMA-based PSUs prevented dilution of shareholders during a multi-year period in which our share price underperformed our expectation, it also meaningfully impaired the retention and motivation value of 3YMA-based PSUs for Cimpress' executives and employees.

The long-term incentive (LTI) awards granted to our executive officers in fiscal year 2024 consisted solely of performance share units with performance targets based on the fiscal year 2024 revenue, adjusted EBITDA, and unlevered adjusted free cash flow of Cimpress (for Cimpress executive officers) or Vista (for Florian Baumgartner). This design maintains focus on both in-year financial performance and, since the awards vest over four years, multi-year share price appreciation. We refer to these performance share units as FY24 PSUs, and throughout this proxy statement we refer to the FY24 PSUs and the 3YMA-based PSUs collectively as PSUs.

As part of the design, the Compensation Committee assigned relative weightings to each financial metric. In fiscal year 2024, the Compensation Committee approved the following weightings:

•fiscal year 2024 revenue: 10%

•fiscal year 2024 adjusted EBITDA: 45%

•fiscal year 2024 unlevered adjusted free cash flow: 45%

After the end of fiscal year 2024, the number of shares issuable pursuant to each FY24 PSU was determined and fixed based on (i) the relative weightings of each financial metric and (ii) the degree of achievement against each performance target, as described further below.

LTI recipients in Cimpress central teams and Vista other than executive officers received a mix of FY24 PSUs and restricted share units (RSUs) depending on their seniority level.

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 2024, 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. We chose the 16 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 2024 are:


Akamai Technologies, Inc.	iRobot Corporation	Teradyne, Inc.
CarGurus, Inc.	New Relic, Inc.	TripAdvisor, Inc.
Cerence, Inc.	Pegasystems, Inc.	Upwork, Inc.
Etsy, Inc.	PTC, Inc.	Yelp, Inc.
HubSpot, Inc.	Rapid7, Inc.
IAC Inc.	Stitch Fix, Inc.

For fiscal year 2024, the principal elements of our compensation program for our named executive officers included base salary, LTI awards in the form of FY24 PSUs, and standard health and welfare benefits that are applicable to employees in each executive's geographic location.

The amount of total target compensation granted to Robert Keane did not change from fiscal year 2023 to fiscal year 2024, but the Compensation Committee adjusted the mix of Mr. Keane's annual cash compensation and LTI compensation to more closely align Mr. Keane's guaranteed cash compensation with other executive officers. Specifically, the Compensation Committee reduced Mr. Keane's base salary by $750,000 to $1,000,000 for fiscal year 2024 while increasing his LTI compensation by $750,000 to $7,250,000. While in fiscal years 2017 through 2023 Mr. Keane received all of his LTI compensation in the form of 3YMA-based PSUs, in fiscal year 2024 he received FY24 PSUs based on the financial performance of Cimpress on a consolidated basis.

For Sean Quinn and Maarten Wensveen, taking into account the totality of the factors described above, the Compensation Committee kept the amount of total target compensation and the mix of annual cash compensation and LTI compensation the same from fiscal year 2023 to fiscal year 2024. Like Mr. Keane, the fiscal year 2024 LTI compensation of Messrs. Quinn and Wensveen consisted of FY24 PSUs based on the financial performance of Cimpress on a consolidated basis.

For Florian Baumgartner, the Compensation Committee maintained his fiscal year 2024 base salary at the same level as fiscal 2023. Mr. Baumgartner received only a small portion of his base salary 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 vest in 16 equal quarterly installments over four years. The Compensation Committee increased the amount of Mr. Baumgartner's annual LTI award for fiscal year 2024 by $250,000 to $2,750,000, consisting of FY24 PSUs based on the financial performance of the Vista business. Mr. Baumgartner's overall LTI compensation was lower in fiscal year 2024 than in fiscal year 2023 due to a one-time RSU award he received in January 2023 in connection with his promotion to CEO, Vista and designation as an executive officer.

Long-Term Incentive Program

In fiscal year 2024, 100% of the LTI compensation we granted to our executive officers was in the form of FY24 PSU awards. Our executive officers also hold legacy 3YMA-based PSU awards granted to them in prior 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 2024.

FY24 Performance Share Units. The financial metrics, performance targets, weightings, and multipliers are as follows:

Fiscal Year 2024 Revenue

Performance Target for Cimpress: $3,264,404,427

Performance Target for Vista: $1,739,717,330

Weighting: 10%

Percentage Achievement

<95%
(Below Threshold)

95%
(Threshold)

100%
(Target)

105% or higher
(Maximum)

Multiplier

60%

100%

160%

Fiscal Year 2024 Adjusted EBITDA

Performance Target for Cimpress: $420,000,000

Performance Target for Vista: $333,842,676

Weighting: 45%

Percentage Achievement

<90%
(Below Threshold)

90%
(Threshold)

100%
(Target)

110% or higher
(Maximum)

Multiplier

60%

100%

160%

Fiscal Year 2024 Unlevered Free Cash Flow

Performance Target for Cimpress: $288,497,675

Performance Target for Vista: $283,470,167

Weighting: 45%

Percentage Achievement

<90%
(Below Threshold)

90%
(Threshold)

100%
(Target)

110% or higher
(Maximum)

Multiplier

60%

100%

160%

Once the Committee determines the multiplier for the FY24 PSU awards based on the level of achievement against the performance targets as outlined above, the awards vest over four years following the grant date subject to continued employment on each vest date.

In August 2024, the Compensation Committee determined that the multiplier for the FY24 PSU awards based on Cimpress' consolidated results is 151% based on 95.23% achievement of the revenue target, 153.58% achievement of the adjusted EBITDA target, and 160% achievement of the unlevered free cash flow target. The Committee determined that the multiplier for the FY24 PSU awards based on Vista's results is 145% based on 104.30% achievement of the revenue target, 139.62% achievement of the adjusted EBITDA target, and 160% achievement of the unlevered free cash flow target. Please see Appendix A attached to this proxy statement for reconciliations of the LTI financial measures to the financial measures reported in our audited financial statements in accordance with generally accepted accounting principles.

Share Options and Restricted Share Units. In previous fiscal years, we granted share options and RSU awards to executives other than Mr. Keane that vest over four years. 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 Performance Share Units. The 3YMA-based PSU awards granted to our executive officers in previous fiscal years 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 would terminate 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 well 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.

Benefit Programs

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, with company matching contributions vesting over a four-year period.

We also provide customary pension plans to our European employees.

Perquisites

In general, executives are not entitled to benefits that are not otherwise available to all other employees who work in the same geographic location. However, in fiscal year 2024 Mr. Keane relocated his primary residence and principal work location for personal reasons, and Cimpress supported this relocation by forming a new subsidiary to serve as Mr. Keane's primary employer and obtaining legal and tax advice relating to Mr. Keane's employment. The external costs that Cimpress incurred in these efforts are considered "perquisites" under SEC rules and are therefore reported in the "All Other Compensation Column" of the Summary Compensation Table below even though Mr. Keane did not receive any payments from Cimpress related to his relocation.

Realized Compensation

To supplement the SEC-required disclosure, the chart below shows the Realized Compensation for each named executive officer. We define "Realized Compensation" as the total of (1) salary received, (2) bonus received, (3) the value of all Cimpress shares issued pursuant to the vesting of share awards including shares withheld for taxes, and (4) the value of Cimpress shares subject to option awards that vested, in each case, during a given fiscal year.

Because the Summary Compensation Table in the Executive Compensation Tables section of this proxy statement 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 our share price at the time of vesting events, an executive's Realized Compensation often varies significantly from the amounts shown in the Summary Compensation Table. The table immediately below compares Realized Compensation to the totals shown in the Summary Compensation Table.


Name and Principal Position	Fiscal Year	Salary ($)	Bonus ($)	Value of Vested Share Award Shares ($)(1)	Value of Vested Option Shares ($)(2)	Realized Compensation ($)	Summary Compensation Table Total ($)
Robert S. Keane	2024	1,000,000	—	—	—	1,000,000	8,284,739
Chairman and Chief Executive	2023	1,756,346	—	—	—	1,756,346	3,077,261
Officer, Cimpress	2022	766,468	—	—	—	766,468	8,133,820

Florian Baumgartner	2024	93,662	200,000	3,209,238	482,106	3,985,006	3,043,607
Executive Vice President and	2023	94,292	200,000	949,626	181,126	1,425,044	3,294,244
Chief Executive Officer, Vista

Sean Quinn	2024	800,000	—	3,459,764	655,621	4,915,385	4,210,093
Executive Vice President and	2023	800,000	—	724,799	246,344	1,771,143	4,209,727
Chief Financial Officer	2022	800,000	129,375	574,051	—	1,503,426	7,351,074

Maarten Wensveen	2024	750,000	—	2,467,068	530,316	3,747,384	3,510,295
Executive Vice President and	2023	750,000	—	370,842	199,240	1,320,082	3,510,296
Chief Technology Officer	2022	750,000	—	362,150	—	1,112,150	5,269,744

(1) The value realized on vesting of share awards is determined by multiplying the number of shares that vested by the closing sale price of our ordinary shares on Nasdaq on the vest date, or on the last trading date immediately before the vest date if the vest date is not a trading date.

(2) The value realized on vesting of option shares is determined by multiplying the number of shares that vested by the difference between the exercise price of the options and the closing sale price of our ordinary shares on Nasdaq on the vest date, or on the last trading date immediately before the vest date if the vest date is not a trading date.

Executive Retention and Other Agreements

Executive Retention Agreements

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 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 the following:

•A lump sum severance payment equal to two years' base salary and 200% of any annual cash incentive award in the case of Mr. Keane, and one year's base salary and 100% of any annual cash incentive award in the case of the other executive officers. The annual cash incentive award portion of this severance payment is based on the amount the executive officer would receive if the applicable performance criteria, if any, were achieved at target levels.

•With respect to any outstanding annual cash incentive award, payment of a pro rata portion of the award (assuming achievement of the applicable performance criteria, if any, at target levels) based on the number of days elapsed from the beginning of the then current fiscal year until the date of termination, less any amount previously paid to the executive under such award.

•With respect to any outstanding multi-year cash incentive award, payment of a pro rata portion of the award (assuming achievement of the applicable performance criteria, if any, at target levels) based on the number of days elapsed from the beginning of the then current performance period until the date of termination, less any amount previously paid to the executive under such award.

•The continuation of all other employment-related benefits for two years after termination for Mr. Keane and one year after termination for the other executive officers.

•If the termination occurs within 12 months after a change in control of Cimpress, then each of the executive officer's share option awards remains exercisable until the earlier of 12 months after termination or the original expiration date of the award.

The executive retention agreements also provide that if 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:

•All equity awards granted to the executive officers will accelerate and become fully vested, with any equity award subject to performance-based vesting being deemed to be earned at 100% of the target levels of performance for such award.

◦However, this acceleration does not apply to 3YMA-based PSU awards or the salary-replacement RSU award granted on January 1, 2021 to Mr. Baumgartner. The accelerated vesting provisions of those awards are described below.

•The performance criteria (if any) applicable to any outstanding annual or multi-year cash incentive awards will be deemed satisfied at 100% of the target levels of performance for such awards, and the executive officers will be entitled to receive 100% of the target amount of each such annual or multi-year award, less any amount previously paid to the executive under such awards.

•Solely in the case of Mr. Keane, if Mr. Keane is required to pay any excise tax pursuant to Section 4999 of the U.S. Internal Revenue Code of 1986 as a result of compensation payments made to him, or benefits he obtained (including the acceleration of equity awards), in connection with a change in ownership or control of Cimpress plc, he will be entitled to receive a gross-up payment equal to the amount 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 $50,000 would eliminate the requirement to pay an excise tax under Section 4999, then Cimpress has the right to reduce the payments by up to $50,000 to avoid triggering the excise tax and thus avoid providing a gross-up payment to Mr. Keane.

3YMA-Based PSU Awards

The equity plans and agreements that govern our 3YMA-based PSUs provide that, upon a change in control, all 3YMA-based 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 calculated as of the change in control date.

Mr. Baumgartner's Salary Replacement RSU Award

The RSU agreement that governs the RSU award Mr. Baumgartner received on January 1, 2021 to replace 88% of his salary over a four-year period provides that if Cimpress terminates Mr. Baumgartner's employment without cause (as defined in the agreement), then the "pro rata portion" of unvested RSUs will accelerate and become vested, but there is no acceleration upon a change in control. The "pro rata portion" of unvested RSUs is equal to (x) the number of RSUs that would have vested on the first vesting date that follows the end of the fiscal quarter in which Mr. Baumgartner's separation date occurs multiplied by (y) the quotient of the number of calendar days from the beginning of the fiscal quarter to the separation date divided by the number of calendar days in such fiscal quarter.

The following table sets forth information about 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, 2024.


Name		Cash Payment ($)(1)	Accelerated Vesting of Share Options ($)(2)	Accelerated Vesting of RSUs and PSUs ($)(3)	Benefits ($)(4)	Tax Gross-Up Payment ($)(5)	Total ($)
Robert S. Keane
•	Termination Without Cause or With Good Reason	2,000,000	—	—	43,479	—	2,043,479
•	Change in Control	—	—	9,027,159	—	—	9,027,159
•	Change in Control w/ Termination Without Cause or With Good Reason	2,000,000	—	9,027,159	43,479	—	11,070,638

Florian Baumgartner (6)
•	Termination Without Cause or With Good Reason	93,662	—	160,502	10,293	—	264,457
•	Change in Control	—	1,129,582	7,925,201	—	—	9,054,783
•	Change in Control w/ Termination Without Cause or With Good Reason	93,662	1,129,582	8,085,703	10,293	—	9,319,240

Sean E. Quinn
•	Termination Without Cause or With Good Reason	800,000	—	—	27,691	—	827,691
•	Change in Control	—	1,536,270	7,901,809	—	—	9,438,079
•	Change in Control w/ Termination Without Cause or With Good Reason	800,000	1,536,270	7,901,809	27,691	—	10,265,770

Maarten Wensveen
•	Termination Without Cause or With Good Reason	750,000	—	—	27,403	—	777,403
•	Change in Control	—	1,242,548	5,911,310	—	—	7,153,858
•	Change in Control w/ Termination Without Cause or With Good Reason	750,000	1,242,548	5,911,310	27,403	—	7,931,261

_____________


(1)			Amounts in this column represent severance amounts payable under the executive retention agreements upon the triggering event described in the first column.

(2)			Amounts in this column represent the value of unvested, in-the-money share options upon the triggering event described in the first column. The value of share options is based on the difference between the exercise price of the options and $87.61 per share, which was the closing price of our ordinary shares on Nasdaq on June 28, 2024, the last trading day of fiscal year 2024.

(3)			Amounts in this column represent the value, based on $87.61 per share, which was the closing price of our ordinary shares on Nasdaq on June 28, 2024, the last trading day of fiscal year 2024, of unvested RSUs and FY24 PSUs that would vest upon the triggering event described in the first column. For 3YMA-based PSUs, we assumed the price paid per share to holders of Cimpress' shares in connection with the change in control would represent a CAGR below the target performance goal for the PSU awards and accordingly that no shares would be issued pursuant to outstanding 3YMA-based PSU awards in a change in control.

(4)			Amounts reported in this column represent the estimated cost of providing employment related benefits (such as insurance for medical, dental, and vision) during the period the named executive officer is eligible to receive those benefits under the executive retention agreements, which is two years for Mr. Keane and one year for the other named executive officers.

(5)			None of our executive officers other than Mr. Keane have excise tax gross-up provisions in their agreements. We calculated the amount of tax gross up to which Mr. Keane would have been entitled if a triggering event had occurred on June 30, 2024 and determined that he would not have been entitled to a gross-up payment based on the assumptions described above.



(6)			The amounts relating to cash payments and welfare benefits for Mr. Baumgartner would be payable in Euros. For purposes of this table, we converted these payments from Euros to U.S. dollars at a currency exchange rate of €1.00 to $1.07658 based on the average currency exchange rate for the month of June 2024.

The Role of Company Executives in the Compensation Process

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.

Share Ownership Guidelines

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:

•Chief Executive Officer: 5 times annual base salary

•Other executive officers: 3 times annual base salary

•Board of Directors: 3 times Board annual cash retainer

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, 2024, all executive officers and directors had satisfied their ownership guideline requirement.

Share Option Granting Practices

We did not grant any share options to executives or employees during fiscal year 2024.

Compensation Committee Report

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 with management, the Compensation Committee recommended to the Board of Directors that the Compensation Discussion and Analysis be included in this proxy statement.

Compensation Committee of the

Board of Directors

Scott J. Vassalluzzo, Chair

Sophie A. Gasperment

Zachary S. Sternberg

EXECUTIVE COMPENSATION TABLES

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:

(i) our principal executive officer,

(ii) our principal financial officer, and

(iii) our other executive officers as of June 30, 2024.

Throughout this proxy statement, we refer to the individuals listed in (i) through (iii) above as our named executive officers.


Name and Principal Position	Fiscal Year	Salary ($)(1)	Bonus ($)(2)	Share Awards ($)(3)	Option Awards ($)(3)	All Other Compensation ($)	Total ($)
Robert S. Keane	2024	1,000,000	—	7,249,901	—	34,838(5)	8,284,739
Chairman and Chief	2023	1,756,346	—	1,320,915	—	—	3,077,261
Executive Officer, Cimpress	2022	766,468	—	7,342,285	—	25,067	8,133,820

Florian Baumgartner(4)	2024	93,662	200,000	2,749,945	—	—	3,043,607
Executive Vice President and	2023	94,292	200,000	1,749,969	1,249,983	—	3,294,244
Chief Executive Officer, Vista

Sean E. Quinn	2024	800,000	—	3,399,997	—	10,096(6)	4,210,093
Executive Vice President	2023	800,000	—	1,699,975	1,699,987	9,765	4,209,727
and Chief Financial Officer	2022	800,000	129,375	6,412,776	—	8,923	7,351,074

Maarten Wensveen	2024	750,000	—	2,749,945	—	10,350(6)	3,510,295
Executive Vice President and	2023	750,000	—	1,374,958	1,374,988	10,350	3,510,296
Chief Technology Officer	2022	750,000	—	4,510,594	—	9,150	5,269,744

_____________


(1)						In fiscal years 2019 through 2022, Mr. Keane received as much of his compensation as possible in the form of 3YMA-based PSUs, within the 75,000 PSUs per fiscal year limit set forth in his PSU Limitation Agreement. For Mr. Keane, the amount in this column for fiscal year 2022 represents the amount of his compensation that exceeded the 75,000 PSUs per fiscal year limit set forth in his PSU Limitation Agreement and was instead paid to him in cash as salary.

(2)						The amounts reported in this column for Messrs. Baumgartner and Quinn represent the payment of cash retention bonuses that were granted in previous fiscal years and vested in the years shown.

(3)						The amounts reported in these columns represent a dollar amount equal to the grant date fair value of the share options and share awards as computed in accordance with FASB ASC Topic 718. You can find the assumptions we used in the calculations for these amounts in Note 11 to our audited financial statements included in our Annual Report on Form 10-K for the fiscal year ended June 30, 2024. See footnote 5 to the Grants of Plan-Based Awards in the Fiscal Year Ended June 30, 2024 table for the value of the FY24 PSUs granted in fiscal year 2024 assuming the maximum achievement of the performance conditions.

(4)						Mr. Baumgartner was designated an executive officer of Cimpress in February 2023 in connection with his promotion to Chief Executive Officer of Vista. The amounts paid to or on behalf of Mr. Baumgartner (other than option and share awards) were paid in Euros. For fiscal year 2024, we converted these payments as reflected in this table from Euros to U.S. dollars at a currency exchange rate of €1.00 to $1.07658 based on the average currency exchange rate for the month of June 2024.

(5)						This amount represents Cimpress' external costs associated with its support of Mr. Keane's relocation of his primary residence and principal work location, including the formation and maintenance of a new subsidiary and obtaining legal and tax advice relating to Mr. Keane's employment.

(6)						This amount represents our matching contributions under our 401(k) deferred savings retirement plans.

Grants of Plan-Based Awards in the Fiscal Year Ended June 30, 2024

The following table contains information about plan-based awards granted to each of our named executive officers during the fiscal year ended June 30, 2024.


		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)
Robert S. Keane	8/15/2023	60,897	101,495	162,392	7,124,949
	12/14/2023	925	1,543	2,468	124,952

Florian Baumgartner	8/15/2023	23,503	39,173	62,676	2,749,945

Sean E. Quinn	8/15/2023	29,059	48,433	77,492	3,399,997

Maarten Wensveen	8/15/2023	23,503	39,173	62,676	2,749,945

___________________________


(1)						These columns represent FY24 PSU awards. Each PSU represents a right to receive between 0 and 1.6 Cimpress ordinary shares upon the satisfaction of (A) service-based vesting, and (B) performance conditions relating to he fiscal year 2024 revenue, adjusted EBITDA, and unlevered free cash flow of Cimpress (for Cimpress executive officers) or Vista (for Florian Baumgartner). The service-based vesting condition is that these FY24 PSU awards vest as to 25% of the number of PSUs subject to the award on August 15, 2024 and as to 6.25% of the number of PSUs every three months thereafter until August 15, 2028.

(2)						These amounts represent the number of Cimpress ordinary shares that would be subject to each FY24 PSU award if the target for the fiscal year 2024 revenue had been achieved at a 95% level and the adjusted EBITDA and unlevered cash flow had been achieved at a 90% level (multiplier of 60%).

(3)						These amounts represent the number of Cimpress ordinary shares that would be subject to each FY24 PSU award if the targets for the fiscal year 2024 revenue, adjusted EBITDA, and unlevered cash flow had been achieved at a 100% level (multiplier of 100%).

(4)						These amounts represent the number of Cimpress ordinary shares that would be subject to each FY24 PSU award if the target for the fiscal year 2024 revenue had been achieved at a 105% level or above and the adjusted EBITDA and unlevered cash flow had been achieved at a 110% level or above (multiplier of 160%).

(5)						The amounts reported in this column represent the grant date fair value for the equity awards computed in accordance with FASB ASC Topic 718. You can find the assumptions we used in the calculations for these amounts in Note 11 to our audited financial statements included in our Annual Report on Form 10-K for the fiscal year ended June 30, 2024. The maximum value of the FY24 PSUs assuming the maximum achievement of the performance conditions is $11,599,777 for Mr. Keane, $4,399,855 for Messrs. Baumgartner and Wensveen, and $5,439,938 for Mr. Quinn. We calculated the maximum values by multiplying the maximum number of shares issuable pursuant to each FY24 PSU award by the closing price of our ordinary shares on Nasdaq on the grant date.

Outstanding Equity Awards at June 30, 2024

The following table contains information about outstanding option awards, unvested RSUs and FY24 PSUs, and unearned shares subject to 3YMA-based PSUs as of June 30, 2024 for each of our named executive officers.


	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)
Robert S. Keane					155,586(5)	13,630,889	93,750(6)	8,213,438
							78,970(7)	6,918,562
							73,498(8)	6,439,160
							10,759(9)	942,596
							91,536(10)	8,019,469
							1,398(11)	122,479
							19,010(12)	1,665,466
							1,403(13)	122,917
							73,335(14)	6,424,879
							79,322(15)	6,949,400
							10,886(16)	953,722
							1,611(17)	141,140
							1,288(18)	112,842
							91,768(19)	8,039,794
							1,981(20)	173,555

Florian Baumgartner	3,410	27,278	46.20	8/15/2032	56,800(5)	4,976,248	10,743(21)	941,194
					1,329(22)	116,434	10,999(23)	963,622
					5,496(24)	481,505	10,451(25)	915,612
					834(26)	73,067
					1,869(27)	163,743
					4,228(28)	370,415
					16,527(29)	1,447,930
					15,219(30)	1,333,337
					11,281(31)	988,328

Sean E. Quinn	37,099	37,099	46.20	8/15/2032	73,133(5)	6,407,182	24,301(6)	2,129,011
					3,988(22)	349,389	20,306(7)	1,779,009
					1,489(26)	130,451	18,898(8)	1,655,654
					5,609(27)	491,404	22,952(32)	2,010,825
					9,977(28)	874,085	19,641(23)	1,720,748
					20,697(30)	1,813,264	19,410(25)	1,700,510

Maarten Wensveen	30,007	30,006	46.20	8/15/2032	59,151(5)	5,182,219	14,400(6)	1,261,584
					3,323(22)	291,128	6,016(7)	527,062
					4,674(27)	409,489	3,651(8)	319,864
					3,563(28)	312,154	18,362(32)	1,608,695


16,740(30)	1,466,591	20,951(23)	1,835,517
		16,175(25)	1,417,092

___________________


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

(2)						These amounts represent the number of Cimpress ordinary shares issuable pursuant to RSU and FY24 PSU awards upon vesting.

(3)						The market value of the unvested RSUs and FY24 PSUs is determined by multiplying the number of shares issuable pursuant to the RSU and FY24 PSU awards by $87.61 per share, which was the closing price of our ordinary shares on Nasdaq on June 28, 2024, the last trading day of fiscal year 2024.

(4)						The market value of the unearned 3YMA-based PSUs is determined by multiplying the number of shares that would be issuable if the conditions described in the footnotes below were achieved by $87.61 per share, which was the closing price of our ordinary shares on Nasdaq on June 28, 2024, the last trading day of fiscal year 2024.

(5)						This amount represents the number of Cimpress ordinary shares issuable pursuant to this FY24 PSU award if the service-based condition is satisfied and reflects the Compensation Committee's determination of the number of ordinary shares earned for each FY24 PSU based on Cimpress' and Vista's actual fiscal year 2024 revenue, adjusted EBITDA, and unlevered free cash flow compared to the performance targets set by the Compensation Committee. The service-based vesting condition is that these FY24 PSU awards vest as to 25% of the number of PSUs subject to the award on August 15, 2024 and as to 6.25% of the number of PSUs every three months thereafter until August 15, 2028, so long as the named executive officer continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan on each vesting date.

(6)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 11% to 11.99% on any August 15 of 2022 through 2026, compared to $69.44, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition has been fully satisfied for these 3YMA-based PSUs, but no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

(7)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 11% to 11.99% on any August 15 of 2023 through 2027, compared to $83.10, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition has been fully satisfied for these 3YMA-based PSUs, but no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

(8)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 11% to 11.99% on any August 15 of 2024 through 2028, compared to $102.68, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition has been fully satisfied for these 3YMA-based PSUs, but no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

(9)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 11% to 11.99% on any February 15 of 2025 through 2029, compared to $109.35, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition has been fully satisfied for these 3YMA-based PSUs, but no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

(10)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 11% to 11.99% on any August 15 of 2025 through 2029, compared to $108.92, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition has been fully satisfied for these 3YMA-based PSUs, but no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

(11)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 11% to 11.99% on any November 15 of 2025 through 2029, compared to $111.70, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition has been fully satisfied for these 3YMA-based PSUs, but no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

(12)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 11% to 11.99% on any August 15 of 2026 through 2030, compared to $112.72, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition has been fully satisfied for these 3YMA-based PSUs, but no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

(13)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 11% to 11.99% on any November 15 of 2026 through 2030, compared to $111.23, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition of these 3YMA-based PSUs is that 25% of the PSUs vest on November 24 of each of 2021 through 2024 so long as Mr. Keane continues to be an eligible participant under Cimpress' 2016 Performance Equity Plan on such vesting date. However, no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.


(14)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 11% to 11.99% on any February 15 of 2027 through 2031, compared to $108.31, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition has been fully satisfied for these 3YMA-based PSUs, but no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

(15)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 11% to 11.99% on any August 15 of 2027 through 2031, compared to $100.46, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition of these 3YMA-based PSUs is that 25% of the PSUs vest on June 30 of each of 2022 through 2025 so long as Mr. Keane continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan on such vesting date. However, no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

(16)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 11% to 11.99% on any August 15 of 2027 through 2031, compared to $100.46, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition has been fully satisfied for these 3YMA-based PSUs, but no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

(17)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 11% to 11.99% on any November 15 of 2027 through 2031, compared to $96.94, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition of these 3YMA-based PSUs is that 25% of the PSUs vest 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 on such vesting date. However, no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

(18)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 11% to 11.99% on any November 15 of 2027 through 2031, compared to $96.94, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition has been fully satisfied for these 3YMA-based PSUs, but no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

(19)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 11% to 11.99% on any November 16 of 2028 through 2032, compared to $78.82, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition of these 3YMA-based PSUs is that 25% of the PSUs vest 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 on such vesting date. However, no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

(20)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 11% to 11.99% on any November 16 of 2028 through 2032, compared to $78.82, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition of these 3YMA-based PSUs is that 25% of the PSUs vest 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 on such vesting date. However, no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

(21)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 9% to 9.99% on any November 15 of 2023 through 2027, compared to $111.70, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition has been fully satisfied for these 3YMA-based PSUs, but no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

(22)						These RSU awards vest as to 25% of the original number of units on July 1 of each of 2021 through 2024, on each of which dates we will automatically issue one ordinary share for each vested unit so long as the named executive officer continues to be an eligible participant under Cimpress' 2011 Equity Incentive Plan on that date.

(23)						This amount represents the number of Cimpress ordinary shares that would be 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. The service-based vesting condition has been fully satisfied for these 3YMA-based PSUs, but no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

(24)						This RSU award vests as to 6.25% of the original number of units on May 15, 2021 and as to an additional 6.25% on the 15th day of every third month thereafter until February 15, 2025, 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 on that date.

(25)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 9% to 9.99% on any August 15 of 2025 through 2029, compared to $100.46, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition for these 3YMA-based PSUs is that 25% of the original number of PSUs vest on June 30 of each of 2022 through 2025 so long as the named executive officer continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan on each vesting date. However, no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

(26)						These RSU awards vest as to 25% of the original number of units on August 15 of each of 2021 through 2024, on each of which dates we will automatically issue one ordinary share for each vested unit so long as the named executive officer continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan on that date.


(27)						These RSU awards vest 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 named executive officer continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan on that date.

(28)						These RSU awards vest as to one third of the original number of units on February 15 of each of 2023 through 2025, on each of which dates we will automatically issue one ordinary share for each vested unit so long as the named executive officer continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan on that date.

(29)						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 on that date.

(30)						These RSU awards vest 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 named executive officer continues to be an eligible participant under Cimpress' 2020 Equity Incentive Plan on that date.

(31)						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 on that date.

(32)						This amount represents the number of Cimpress ordinary shares that would be issuable if the 3YMA CAGR is 9% to 9.99% on any August 15 of 2023 through 2027, compared to $108.92, which was the 3YMA of Cimpress' ordinary shares on the grant date. The service-based vesting condition has been fully satisfied for these 3YMA-based PSUs, but no shares will be earned or issuable until the 3YMA on a measurement date meets or exceeds the CAGR performance thresholds.

Options Exercised and Shares Vested in the Fiscal Year Ended June 30, 2024

The following table contains information about option exercises and vesting of RSUs on an aggregated basis during fiscal year 2024 for each of our named executive officers. No shares were issued pursuant to PSUs during fiscal year 2024.


	Option Awards		Share Awards
Name	Number of Shares Acquired on Exercise (#)	Value Realized on Exercise ($)(1)	Number of Shares Acquired on Vesting (#)	Value Realized on Vesting ($)(2)
Robert S. Keane	—	—	—	—
Florian Baumgartner	23,869	1,016,829	39,882	3,209,238
Sean E. Quinn	—	—	45,978	3,459,764
Maarten Wensveen	—	—	33,864	2,467,068

_________________________


(1)						The value received on exercise of share options is determined by multiplying the number of shares exercised by the difference between the closing sale price of our ordinary shares on Nasdaq on the date of exercise and the exercise price.

(2)						The value realized on vesting of RSUs is determined by multiplying the number of shares that vested by the closing sale price of our ordinary shares on Nasdaq on the vest date, or on the last trading date immediately before the vest date if the vest date is not a trading date.

CEO Pay Ratio

Mr. Keane's fiscal year 2024 annual total compensation was $8,284,739, as reported in the Summary Compensation Table above, and the fiscal year 2024 annual total compensation of our median compensated employee other than Mr. Keane was $28,970. The ratio of the median employee's total compensation to Mr. Keane's total compensation is 1-to-286. As supplemental information, Mr. Keane's Realized Compensation for fiscal year 2024, as described above in the Compensation Discussion and Analysis section, was $1,000,000, which yields a ratio of 1-to-35.

Because there were no changes to our employee population or employee compensation from fiscal year 2023 to fiscal year 2024 that significantly impacted our pay ratio disclosure, we used the same median employee for fiscal year 2024 as we did for fiscal year 2023. 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 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.

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 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. The "compensation actually paid" amounts for fiscal years 2023, 2022, and 2021 set forth in the table below have been revised to reflect the Compliance and Disclosure Interpretations relating to Item 402(v) of Regulation S-K that the SEC published in the second half of calendar year 2023, and these amounts are therefore different from the "compensation actually paid" amounts for fiscal years 2023, 2022, and 2021 reported in the Pay Versus Performance table in our proxy statement dated October 26, 2023.

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. 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.

“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. See the discussion of "Realized Compensation" in the Compensation Discussion and Analysis section of this proxy statement for a calculation of compensation realized or realizable by our executives in each fiscal year.

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)
2024	8,284,739	21,341,751	3,587,998	8,308,863	114.76	123.66	173,682	457,503
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

_____________

(1) Mr. Keane served as our principal executive officer for each of fiscal years 2021, 2022, 2023, and 2024. 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.


Adjustments to Determine CEO Compensation Actually Paid	2024	2023	2022	2021
Summary Compensation Table Total	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	(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	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	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	—	—	—	—
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	21,341,751	15,721,823	(30,575,430)	18,254,681

(2) The Other NEOs whose compensation amounts are averaged and included in this table are Sean Quinn and Maarten Wensveen for all four fiscal years and Florian Baumgartner for fiscal years 2023 and 2024 only. 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.


Adjustments to Determine Average Other NEO Compensation Actually Paid	2024	2023	2022	2021
Summary Compensation Table Total (Average)	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	(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	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	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	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	8,308,863	7,673,690	(5,800,169)	7,884,721

(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 four of the covered fiscal years. The cumulative total returns to shareholders of Cimpress ordinary shares and the RDG Internet Composite index are calculated by assuming an investment of $100 (with reinvestment of all dividends) was made in our ordinary shares and in the index on June 30, 2020.

(4) The amounts in this column are Cimpress' net income (loss) reflected in the audited financial statements published in our Annual Report on Form 10-K for the applicable year.

(5) The FY24 PSU awards granted to our executive officers are based in part on 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 the Compensation Committee, as described in more detail in the Compensation Discussion and Analysis section of this proxy statement. Vista's segment EBITDA for fiscal year 2023 was $224,081 (in thousands), and Vista's adjusted EBITDA for fiscal year 2024 as calculated in accordance with the FY24 PSU awards was $355,889 (in thousands). Please see Appendix A attached to this proxy statement for descriptions and reconciliations of Cimpress' and Vista's adjusted EBITDA.

Relationship between Compensation Actually Paid and Performance Metrics

The following graph shows the relationship between the amount of compensation actually paid to Mr. Keane and the average amount of compensation actually paid to the Other NEOs and the total shareholder return of Cimpress and its peer group, as set forth in the Pay Versus Performance Table above.

Compensation Actually Paid vs. Cimpress TSR and Peer Group TSR

The following graph shows the relationship between the amount of compensation actually paid to Mr. Keane and the average amount of compensation actually paid to the Other NEOs and Cimpress' net income (loss) for each fiscal year, as set forth in the Pay Versus Performance Table above.

Compensation Actually Paid vs. Cimpress Net Income (Loss)

The following graph shows the relationship between the amount of compensation actually paid to Mr. Keane and the average amount of compensation actually paid to the Other NEOs and Cimpress' adjusted EBITDA for each fiscal year, as set forth in the Pay Versus Performance Table above.

Compensation Actually Paid vs. Cimpress Adjusted EBITDA

Lists of Performance Measures for fiscal year 2024

The following are the financial performance measures that Cimpress has determined are our most important financial measures used by Cimpress to link executive compensation actually paid (as calculated above) to our named executive officers other than Mr. Baumgartner for fiscal year 2024 to performance.

•Cimpress adjusted EBITDA

•Cimpress adjusted unlevered free cash flow

•Cimpress adjusted revenue

The following are the financial performance measures that Cimpress has determined are our most important financial measures used by Cimpress to link executive compensation actually paid (as calculated above) to Mr. Baumgartner for fiscal year 2024 to performance.

•Vista adjusted EBITDA

•Vista adjusted unlevered free cash flow

•Vista adjusted revenue

PROPOSAL 3 - AMEND OUR 2020 EQUITY INCENTIVE PLAN TO INCREASE

THE NUMBER OF ORDINARY SHARES ISSUABLE

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. In recent years we have seen the competitiveness for qualified candidates intensify, and we are often vying for qualified candidates against both larger, established companies with significant cash and equity resources and earlier-stage companies that offer significant equity upside. Our compensation program for senior members of our team is heavily focused on the use of equity incentive compensation, and our ability to offer equity awards is a critical tool for remaining competitive and motivating high levels of performance. Moreover, equity incentives align the interests of the employees with the long-term interests of our shareholders.

On September 9, 2024, our Board of Directors approved an amendment to our 2020 Equity Incentive Plan to increase the number of ordinary shares issuable under the plan by an additional 2,000,000 shares, subject to shareholder approval of the amendment at the annual meeting (as so amended, the 2020 Plan). The 2020 Plan is the only plan under which we issue equity awards.

We are seeking an increase in the number of ordinary shares issuable under the 2020 Plan for multiple reasons. First, as of August 20, 2024, there were only 221,002 ordinary shares available for issuance under the 2020 Plan, which is insufficient for our hiring and retention needs. Second, although we no longer grant 3YMA-based PSU awards, as of August 20, 2024, the 2020 Plan has 1,116,760 shares reserved for previously granted 3YMA-based PSUs that are unlikely to pay out in shares at the highest multiple, or perhaps at all, and therefore the risk of dilution from outstanding 3YMA-based PSUs is very low. Conversely, the shareholder value creation, net of dilution, if those 3YMA-based PSUs do pay out would be very high.

We currently reserve 2.5 shares from the 2020 Plan for each 3YMA-based PSU, which is the number of shares issuable if the highest performance threshold (20% or higher 3YMA CAGR) is achieved, but that is unlikely to occur. Our 3YMA-based PSU awards pay out in shares only if the 3YMA reaches or exceeds certain CAGR thresholds, which requires that the 3YMA steadily increase over a long period of time. However, our 3YMA has decreased from $112.72 on August 15, 2020 to $61.59 on August 15, 2024, and the table below shows the minimum 3YMA required to satisfy the CAGR thresholds as of various dates for any shares to be issued under any of the 3YMA-based PSU awards outstanding under the 2020 Plan that are held by our executives and employees (other than Robert Keane, whose 3YMA-based PSU awards have a performance period of six to ten years and a higher minimum 3YMA CAGR threshold of 11%).


Grant Date of PSU Award	Earliest Potential Payout Date	Final Potential Payout Date	Anniversary of Grant Date
			4th anniversary	5th anniversary	6th anniversary	7th anniversary	8th anniversary
			CAGR Threshold and Minimum 3YMA Target for Payout
			9% CAGR	9% CAGR	9% CAGR	9% CAGR	7% CAGR
2/15/2021	2/15/2025	2/15/2029	$134.75	$146.88	$160.10	$174.50	$164.02
5/15/2021	5/15/2025	5/15/2029	$146.66	$159.86	$174.25	$189.93	$178.52
8/15/2021	8/15/2025	8/15/2029	$141.81	$154.57	$168.48	$183.64	$172.61
11/15/2021	11/15/2025	11/15/2029	$136.84	$149.15	$162.58	$177.21	$166.56

If we do not achieve the 3YMA targets above, then each 3YMA-based PSU award will expire on the applicable Final Potential Payout Date above, no shares would be issued pursuant to the awards, and the shares reserved in respect of such awards would become available for issuance under the 2020 Plan.

There were also 951,224 outstanding 3YMA-based PSUs under our 2016 Performance Equity Plan (the 2016 Plan) as of August 20, 2024, and shares subject to PSUs under the 2016 Plan that expire, terminate, or are otherwise surrendered, canceled or forfeited are added to the 2020 Plan on a 1:1 basis. If the 3YMA CAGR thresholds for PSU awards under the 2016 Plan are not achieved before the expiration date for each award, then the awards will expire, with the first tranche of awards expiring on August 15, 2026 if the minimum 3YMA target of $136.60 is not achieved on that date. We estimate that approximately 815,000 shares will be added to the 2020 Plan from the 2016 Plan between August 15, 2026 and August 15, 2028 (inclusive) if none of the minimum 3YMA targets is achieved for awards under the 2016 Plan; the minimum 3YMA thresholds for these awards range from $136.60 to $291.55.

We welcome investors’ questions about the proposed amendment to the 2020 Plan. Please submit your questions to Meredith Burns in Investor Relations at ir@cimpress.com by October 25, 2024, and we will provide written answers in a supplemental proxy filing.

Summary of Material Features of the Plan

The material features of the 2020 Plan, as amended, are as follows:

•If our shareholders approve the amendment to the 2020 Plan to increase the number of ordinary shares issuable under the plan by an additional 2,000,000 shares, then the maximum number of ordinary shares issuable under the 2020 Plan will be 7,500,000 plus an additional number of ordinary shares equal to the number of 3YMA-based PSUs (on a 1:1 basis) outstanding under the 2016 Plan that expire, terminate, or are otherwise surrendered, canceled or forfeited.

•The 2020 Plan permits the award of share options (both incentive stock options and non-statutory share options), share appreciation rights, restricted shares, restricted share units, other share-based awards, and dividend equivalent rights.

•Shares tendered or held back for taxes will not be added back to the reserved pool under the 2020 Plan. Upon the exercise of a share appreciation right that is settled in ordinary shares, the full number of shares underlying the award will be charged to the reserved pool. Additionally, shares we reacquire on the open market will not be added to the reserved pool under the 2020 Plan.

•Share options and share appreciation rights may not be repriced in any manner without shareholder approval.

•Any dividends and dividend equivalent rights payable with respect to any equity award are subject to the same vesting provisions as the underlying award.

•Any material amendment to the 2020 Plan is subject to approval by our shareholders.

•The 2020 Plan will expire on November 25, 2030.

Based solely on the closing price of our ordinary shares as reported by Nasdaq on August 20, 2024, which was $86.48 per share, and the 6,066,473 shares that either were reserved for future issuance pursuant to outstanding awards as of that date or would have been available for awards under the 2020 Plan if the plan had been amended as of such date, the maximum aggregate market value of the ordinary shares that could potentially be issued under the 2020 Plan is $524,628,585.

Our Grant Practices

As of August 20, 2024, there were 221,002 ordinary shares available for issuance under the 2020 Plan, which is the only plan under which we issue equity awards. As of August 20, 2024, the outstanding awards under all of our equity compensation plans, including legacy plans under which we no longer grant awards, consisted of the following:

•share options to acquire 317,077 ordinary shares, with a weighted average exercise price of $46.40 and a weighted average remaining term of 7.6 years

•full value awards in the form of 3YMA-based PSUs covering1,397,928 ordinary shares on a 1:1 basis and 3,494,820 ordinary shares assuming maximum achievement of the performance conditions (which is extremely unlikely)

•full value awards in the form of PSUs with performance conditions based on Cimpress' financial results for fiscal year 2025 covering 449,707 ordinary shares on a 1:1 basis and 719,531 ordinary shares assuming maximum achievement of the performance conditions

•unvested full value awards in the form of FY24 PSUs covering 561,110 ordinary shares and RSUs covering 1,140,479 ordinary shares

Other than as described above, no awards were outstanding under our equity compensation plans as of August 20, 2024.

Below is information regarding historical awards granted and earned:

•Fiscal year 2025 to date (July 1, 2024 - August 20, 2024, which includes our annual LTI grants to employees):

◦No share options granted

◦Full-value time-based awards: 295,945 RSUs granted; no restricted shares granted

◦Full-value performance awards: 449,707 PSUs granted (with performance targets based on fiscal year 2025 financial results), 235,584 incremental shares earned pursuant to FY24 PSUs, and no shares earned pursuant to 3YMA-based PSUs

◦25,256,653 ordinary shares outstanding at August 20, 2024

•Fiscal year 2024:

◦No share options granted

◦Full-value time-based awards: 344,268 RSUs granted; no restricted shares granted

◦Full-value performance awards: 544,120 FY24 PSUs granted and no shares earned pursuant to PSUs

◦26,151,968 weighted average ordinary shares outstanding (basic)

•Fiscal year 2023:

◦Share options to purchase 436,211 shares granted

◦Full-value time-based awards: 1,120,951 RSUs granted; no restricted shares granted

◦Full-value performance awards: 75,000 3YMA-based PSUs granted and no shares earned pursuant to PSUs

◦26,252,860 weighted average ordinary shares outstanding (basic)

•Fiscal year 2022:

◦No share options granted

◦Full-value time-based awards: 771,671 RSUs granted; no restricted shares granted

◦Full-value performance awards: 215,899 3YMA-based PSUs granted and no shares earned pursuant to PSUs

◦26,094,842 weighted average ordinary shares outstanding (basic)

•Share options granted under the 2020 Plan since the plan's inception:

◦Robert Keane, Chairman and Chief Executive Officer, Cimpress: 0

◦Florian Baumgartner, Executive Vice President and Chief Executive Officer, Vista: share option to purchase 54,557 shares

◦Sean Quinn, Executive Vice President and Chief Financial Officer: share option to purchase 74,198 shares

◦Maarten Wensveen, Executive Vice President and Chief Technology Officer: share option to purchase 60,013 shares

◦Current directors who are not executive officers: 0

◦All employees other than executive officers: 247,443

Each RSU represents Cimpress' commitment to issue one ordinary share upon vesting. Each FY24 PSU based on Cimpress' consolidated financial results represents Cimpress' commitment to issue 1.51 ordinary shares upon vesting based on achievement of the applicable financial results for fiscal year 2024, and each FY24 PSU based on the financial results of the Vista business represents Cimpress' commitment to issue 1.45 ordinary shares upon vesting based on achievement of the applicable financial results for fiscal year 2024. Each 3YMA-based PSU represents a right to receive between 0 and 2.5 ordinary shares upon the satisfaction of both service-based vesting over time and performance conditions relating to the compound annual growth rate of Cimpress' three-year moving average share price over a multiple-year period determined by our Board.

Description of our 2020 Plan This summary of the 2020 Plan, as amended, is qualified in its entirety by the text of the 2020 Plan as proposed to be amended attached as Appendix B to this proxy statement as filed with the SEC.

Types of Awards; Authorized Number of Ordinary Shares and Share Counting The 2020 Plan provides for the grant of incentive stock options, non-statutory share options, share appreciation rights, restricted shares, restricted share units, other share-based awards, and dividend equivalent rights, to which we refer in this proxy

statement collectively as awards. Subject to adjustment in the event of stock splits, stock dividends and other similar events and assuming shareholders approve the proposed amendment to increase the number of shares issuable under the 2020 Plan, we may make awards under the 2020 Plan for up to 7,500,000 of our ordinary shares plus an additional number of ordinary shares equal to the number of 3YMA-based PSUs currently outstanding under the 2016 Plan that expire, terminate or are otherwise surrendered, canceled or forfeited. Ordinary shares underlying awards under the 2020 Plan and ordinary shares underlying 3YMA-based PSUs under the 2016 Plan on the basis of one ordinary share for each PSU that expires, terminates or is otherwise surrendered, canceled or forfeited, or is not issued will become available for the grant of new awards under the 2020 Plan. We will not add back to the number of ordinary shares available for the grant of awards under the 2020 Plan any ordinary shares that a participant delivers to Cimpress (whether by actual delivery, attestation or net exercise) to (1) purchase ordinary shares upon the exercise of an award or (2) satisfy tax withholding obligations (including shares retained from the award creating the tax obligation). Similarly, ordinary shares that we may acquire on the open market, whether using the proceeds from the exercise of awards or using other funds, do not increase the number of shares available for future grant of awards.

Description of Awards

Incentive Stock Options and Non-statutory Share Options. Optionees receive the right to purchase a specified number of ordinary shares at a specified exercise price and subject to such other terms and conditions as we specify in connection with the option grant. The exercise price of the options may not be less than 100% of the fair market value per ordinary share on the date the option is granted, unless our Board approves the grant of an option with an exercise price to be determined on a future date, in which case the exercise price may not be less than 100% of the fair market value on such future date. Fair market value for this purpose is determined by reference to the price of the ordinary shares on Nasdaq. Options may not have a term in excess of ten years. The 2020 Plan allows optionees to pay the exercise price of options through the following forms of payment: (a) cash or check, (b) a “cashless exercise” through a broker, (c) subject to certain conditions, surrender of ordinary shares to Cimpress, (d) subject to certain conditions, in the case of non-statutory share options, by “net exercise,” (e) any other lawful consideration as our Board may determine, or (f) any combination of these forms of payment. To qualify as incentive stock options, options must meet additional federal tax requirements, including a $100,000 limit on the value of ordinary shares subject to incentive stock options that first become exercisable by a participant in any one calendar year.

Share Appreciation Rights. A share appreciation right, or SAR, is an award entitling the holder, upon exercise, to receive an amount of our ordinary shares or cash or a combination thereof determined by reference to appreciation, from and after the date of grant, in the fair market value of an ordinary share over the measurement price established pursuant to the applicable SAR agreement. The measurement price may not be less than 100% of the fair market value of our ordinary shares on the date the SAR is granted, unless the Board approves the grant of an SAR effective as of a future date, in which case the measurement price may not be less than 100% of the fair market value on such future date. SARs may be granted independently or in tandem with an option. SARs may not have a term in excess of ten years.

Restricted Share Awards. A restricted share award is a grant of our ordinary shares subject to our right to acquire by way of redemption all or some of the shares from the recipient if the conditions specified in the award are not satisfied before the end of the restriction period established for the award. Our Board determines the terms and conditions of restricted share awards, including the purchase price, if any. Any dividends that we may pay during the vesting period of restricted share awards will accrue but not be paid to the participant until and only to the extent the restricted share award vests.

Restricted Share Unit Awards. A restricted share unit award entitles the recipient to receive ordinary shares or cash at the time the award vests pursuant to the terms and conditions that our Board determines.

Other Share-Based Awards. We may grant under the 2020 Plan other awards that are based on our ordinary shares pursuant to the terms and conditions that our Board determines, including awards of our ordinary shares and other awards that are valued in whole or in part by reference to, or are otherwise based on, ordinary shares or other property.

Dividend Equivalent Rights. We may grant dividend equivalent rights to participants as a component of a restricted share unit award, which entitle the recipient to receive credits for dividends that would be paid if the recipient held the ordinary shares underlying the restricted share unit award. Dividend equivalent rights granted as a

component of a restricted share unit award may be paid only if the related restricted share units become vested. Dividend equivalent rights may be settled in cash, ordinary shares of common stock or a combination thereof, as determined by the Board.

Eligibility to Receive Awards Employees, officers, directors, consultants and advisors of Cimpress and its subsidiaries and of other business ventures in which Cimpress has a controlling interest are eligible to be granted awards under the 2020 Plan. Under present law, however, incentive stock options may be granted only to employees of Cimpress and its subsidiaries. As of August 20, 2024, approximately 15,000 employees, including our four executive officers, and the four non-employee directors who serve on our Board were eligible to receive awards under the 2020 Plan. Although the 2020 Plan permits awards to consultants and advisors, we grant awards to consultants or advisors only in rare instances, and we do not track how many individuals may be providing consulting or advising services to us at any given time. The granting of awards under the 2020 Plan is discretionary, and we cannot now determine the number or type of awards to be granted in the future to any particular person or group.

Transferability of Awards A person who is granted an award under the 2020 Plan may not sell, assign, transfer, pledge or otherwise encumber such award, either voluntarily or by operation of law, except by will or the laws of descent and distribution or, other than in the case of an incentive stock option and awards subject to Section 409A of the US Tax Code, pursuant to a qualified domestic relations order. During the life of the participant, only the participant may exercise such award. However, the Board may permit or provide in an award for the gratuitous transfer of the award by a participant without consideration, subject to any limitations that the Board deems appropriate.

Administration of the 2020 Plan The Board administers the 2020 Plan and has the authority to grant awards and adopt, amend and repeal such administrative rules, guidelines and practices relating to the plan as it deems advisable. The Board may delegate any or all of its powers under the 2020 Plan to one or more committees or subcommittees of the Board, and, subject to certain limits, the Board may also delegate to one or more of our officers the power to grant awards to Cimpress employees or officers who are not executive officers, Section 16 officers, or members of the Board and to exercise such other powers under the 2020 Plan as the Board may determine. Our Board, or any committee to which our Board delegates authority, as the case may be, selects the recipients of awards and determines (a) the number of ordinary shares covered by awards and the dates upon which such awards become exercisable, issuable or otherwise vest; (b) the exercise, measurement or purchase price of awards (which may not be less than 100% of the fair market value of our ordinary shares on the date of grant for options and SARs); (c) the duration of awards (which may not exceed ten years for options and SARs), and (d) the terms and conditions of such awards.

Adjustments for Changes in our Ordinary Shares and Certain Other Events We are required to make equitable adjustments, in the manner determined by our Board, in connection with the 2020 Plan and any outstanding awards to reflect stock splits, stock dividends, recapitalizations, spin-offs and other similar changes in our capitalization. The 2020 Plan also contains provisions addressing the consequences of any Reorganization Event, which is defined as (a) any merger or consolidation of Cimpress with or into another entity as a result of which all of our ordinary shares are converted into or exchanged for the right to receive cash, securities or other property, or are canceled; (b) the transfer or disposition of all of our ordinary shares for cash, securities or other property pursuant to a share exchange or other transaction; (c) the sale of all or substantially all of the assets of Cimpress on a consolidated basis to an unrelated person or entity; (d) any other transaction in which the owners of Cimpress’ outstanding voting power immediately prior to such transaction do not own at least a majority of the outstanding voting power of Cimpress or any successor entity immediately upon completion of the transaction other than as a result of the acquisition of securities directly from Cimpress; or (e) any liquidation or dissolution of Cimpress. In connection with a Reorganization Event, our Board may take any one or more of the following actions as to all or any outstanding awards (other than restricted share awards) on such terms as our Board determines: (i) provide that the acquiring or succeeding corporation (or an affiliate thereof) assume such awards or substitute substantially equivalent awards; (ii) upon written notice to a participant, provide that all of the participant’s unexercised awards will terminate immediately before the consummation of the Reorganization Event unless exercised by the participant; (iii) provide that outstanding awards become exercisable, realizable, or deliv

SEC Form DEF 14A filed by Cimpress plc