UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549 

SCHEDULE 14A 

Proxy Statement Pursuant to Section 14(a) of
the Securities Exchange Act of 1934 (Amendment No.          ) 

Notice of 2023

Annual General Meeting

Of Members and

Proxy Statement

LETTER FROM THE BOARD OF DIRECTORS

FROM OUR BOARD OF DIRECTORS

Dear Fellow Shareholders:

As your Board of Directors, we oversee White Mountains’ efforts to create superior growth in intrinsic value per share over long periods of time. Your Company seeks to achieve this goal by making opportunistic and value-oriented acquisitions of businesses in the insurance, financial services and related sectors, operating these businesses and, if and when attractive exit valuations become available, disposing of these businesses. Since the Company’s IPO in 1985, we have delivered annualized growth in book value per share of 13% and market value per share of 12%.

2022 was an excellent year for your Company. We finished 2022 with book value per share of $1,457 and adjusted book value per share of $1,495, increases of 24% and 26% for the year, respectively. Total shareholder return was 40% in 2022, compared to -18% for the S&P 500 and 19% for the S&P 500 P&C Insurance Index. The successful sale of NSM in August was the main driver, generating a net gain of $876 million, adding roughly $300 to adjusted book value per share.

Away from NSM, the majority of our operating businesses had very good years. Ark produced strong underwriting results while growing premiums 37%. BAM generated $147 million of premiums and member surplus contributions. Kudu had a good all-around year, growing its business and closing three new deployments and two value-adding exits. Your Company also added value through capital management activity. White Mountains completed a self-tender offer in September, repurchasing approximately 328,000 shares for $459 million ($1,400 per share). And at year end, we successfully launched Outrigger Re, deploying $205 million of capital.

The businesses we own today position us well for the future. As is the White Mountains “way,” we are always prospecting for new deployment opportunities, via our “platform business” and at the parent company.

Ongoing Dialogue with Shareholders Through Proactive Engagement

Over the last year, members of the Board and management reached out to shareholders owning 71% of White Mountains’s shares outstanding and met with all shareholders--representing 32% of our shares outstanding--who accepted a meeting. Feedback from these shareholder discussions over the past few years has informed changes to our executive compensation program, enhanced disclosures about the skills and areas of expertise of our Board, and improvements to our ESG, risk management and human capital management practices. This year, these shareholder discussions focused primarily on our business strategy, corporate governance--including the structure and the composition of our Board--and compensation philosophy. Shareholders were overwhelmingly supportive, while also providing valuable feedback, which we have used to further enhance our proxy statement disclosures.

Our core principles served us well in 2022. It is a privilege to serve as your Board, and we value highly your support of White Mountains.

Sincerely,

The White Mountains Insurance Group Board of Directors

April 5, 2023

White Mountains Insurance Group, Ltd. (the “Company”, “Registrant” or “WTM”) is an exempted Bermuda limited liability company whose principal businesses are conducted through its subsidiaries and affiliates. Within this proxy statement, the term “White Mountains” is used to refer to one or more entities within the consolidated organization, as the context requires.

White Mountains is engaged in the business of making opportunistic and value-oriented acquisitions of businesses and assets in the insurance, financial services and related sectors, operating these businesses and assets through its subsidiaries and, if and when attractive exit valuations become available, disposing of these businesses and assets.

As of December 31, 2022, White Mountains conducted its business primarily in four areas: municipal bond insurance, property and casualty insurance and reinsurance, capital solutions for asset and wealth management firms and other operations. White Mountains’s municipal bond insurance business is conducted through its subsidiary HG Global Ltd. and its reinsurance subsidiary HG Re Ltd. (“HG Re”), (collectively, “HG Global”). HG Global was established to fund the startup of and provide reinsurance, through HG Re, to Build America Mutual Assurance Company (“BAM”), a mutual municipal bond insurance company (collectively, “HG Global”). White Mountains’s property and casualty insurance and reinsurance business is conducted through its subsidiary Ark Insurance Holdings Limited and its subsidiaries (collectively, “Ark”). White Mountains provides capital solutions for asset and wealth management firms through its subsidiary Kudu Investment Management, LLC and its subsidiaries (collectively, “Kudu”). White Mountains’s Other Operations consists of the Company and its wholly-owned subsidiary, White Mountains Capital, LLC (“WM Capital”), its other intermediate holding companies, its wholly-owned investment management subsidiary, White Mountains Advisors LLC (“WM Advisors”), investment assets managed by WM Advisors, its interests in MediaAlpha, Inc. (“MediaAlpha”), PassportCard Limited (“PassportCard”) and DavidShield Life Insurance Agency (2000) Ltd. (“DavidShield”) (collectively, “PassportCard/ DavidShield”), Elementum Holdings LP (“Elementum”), Outrigger Re Ltd. Segregated Account 2023-1 (“WM Outrigger Re”), certain other consolidated and unconsolidated entities and certain other assets. As of December 31, 2022, White Mountains’s reportable segments were HG Global/BAM, Ark and Kudu with our remaining operating businesses, holding companies and other assets included in Other Operations.

The 2023 Annual General Meeting will be confined to a shareholder vote on the proposals set forth in this Proxy Statement and on such other matters properly brought before the meeting.

For a reconciliation of non-GAAP measures used in this Proxy Statement to their most comparable GAAP measures, see Annex A.

PROXY SUMMARY

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

This Proxy Statement and the accompanying proxy card are being distributed and made available to shareholders on or about April 21, 2023.

For more information on our corporate governance practices, please refer to page 18 of the proxy statement.

For more information on our commitment to ongoing shareholder engagement and details of our 2022 shareholder outreach, please refer to page 18 of the proxy statement.

Chief Executive Officer:

Other NEOs:

The specifics of our compensation program begin on page 28 of the proxy statement.

To achieve our goal of creating superior growth in the Company’s intrinsic value per share over the long term, and in order to steward our owners’ capital effectively, our Board and management are committed to sustainability and corporate responsibility. In 2020, with oversight from the Board, White Mountains embarked on a project designed to improve our ESG practices and disclosures. We identified ESG priorities that align with both our Company’s business strategy as well as industry and investor expectations. The Board had oversight of this process and final approval of the ESG focus areas and actions, which include:

For more information on our ESG practices, please refer to page 23 or the ESG landing page on our Company website (www.whitemountains.com/esg/).

WHITE MOUNTAINS INSURANCE GROUP, LTD.

NOTICE OF 2023 ANNUAL GENERAL MEETING OF MEMBERS

TO BE HELD MAY 25, 2023

Notice is hereby given that the 2023 Annual General Meeting of Members of White Mountains Insurance Group, Ltd. will be held on Thursday, May 25, 2023 at 8:00 am Atlantic Time at Rosewood Bermuda Hotel, 60 Tucker’s Point Drive, Hamilton Parish, Bermuda. At this meeting, you will be asked to consider and vote upon the following proposals:

The Company’s audited financial statements for the year ended December 31, 2022, as approved by the Company’s Board of Directors, will be presented at this Annual General Meeting.

Shareholders of record of common shares on the record date, Monday, April 3, 2023, (1) who are individuals, may attend and vote at the meeting in person or by proxy or (2) that are corporations or other entities, may have their duly authorized representative attend and vote at the meeting in person or by proxy. A list of all Shareholders entitled to vote at the meeting will be open for public examination during regular business hours beginning on or about April 21, 2023 at the Company’s registered office located at Clarendon House, 2 Church Street, Hamilton HM 11, Bermuda.

Shareholders are invited to complete and sign the accompanying proxy card to be returned to White Mountains Insurance Group, Ltd., Proxy Services, c/o Computershare Investor Services, P.O. Box 43101, Providence, RI 02940-5067, in the envelope provided, whether or not they expect to attend the meeting. Shareholders may also vote their shares by telephone or via the internet in accordance with the instructions on your proxy card.

WHITE MOUNTAINS INSURANCE GROUP, LTD.

PROXY STATEMENT

This Proxy Statement is being furnished in connection with the solicitation of proxies on behalf of the Company’s Board of Directors (the “Board”) for the 2023 Annual General Meeting of Members (the “2023 Annual Meeting”), to be held on Thursday, May 25, 2023 at Rosewood Bermuda Hotel, 60 Tucker’s Point Drive, Hamilton Parish, Bermuda.

Holders of the Company’s common shares (“Shareholders”), par value $1.00 per share, as of the close of business on Monday, April 3, 2023, the record date, are entitled to vote at the meeting. The solicitation of proxies will be made primarily by mail, and the Proxy Statement and related proxy materials will be distributed to registered Shareholders on or about April 21, 2023.

You can ensure that your common shares are properly voted at the meeting by completing, signing, dating and returning the enclosed proxy card in the envelope provided. Shareholders may also vote their shares by telephone or via the internet in accordance with the instructions on your proxy card. Shareholders have the right to appoint another person (who need not be a Shareholder) to represent the Shareholder at the meeting by completing an alternative form of proxy which can be obtained from the Corporate Secretary or by notifying the Inspectors of Election (see page 61). Every Shareholder entitled to vote has the right to do so either in person or by one or more persons authorized by a written proxy executed by such Shareholder and filed with the Corporate Secretary. Any proxy duly executed will continue in full force and effect unless revoked by the person executing it in writing or by the filing of a subsequent proxy.

Sending in a signed proxy will not affect your right to attend the meeting and vote. If a Shareholder attends the meeting and votes in person, his or her signed proxy is considered revoked.

IMPORTANT VOTING INFORMATION

If you hold your shares through a broker, bank or other financial institution, in order for your vote to be counted on any matter other than Proposal 4 (the ratification of the selection of PwC as the Company’s auditor for 2023), you must provide specific voting instructions to your broker, bank or financial institution by completing and returning the proxy card or following the instructions provided to you to vote your shares via telephone or the internet. Voting deadlines vary by institution. Please check with your broker, bank or other financial institution for the voting cut-off date for WTM.

Your Participation in Voting the Shares You Own Is Important

Voting your shares is important to ensure that you have a say in the governance of your company. Please review the proxy materials and follow the instructions on the proxy card to vote your shares. We hope you will exercise your rights and fully participate in your Company’s future.

More Information Is Available

If you have any questions about this rule or the proxy voting process in general, please contact the broker, bank or other financial institution where you hold your shares. The U.S. Securities and Exchange Commission (“SEC”) has information available on the internet at: https://www.investor.gov/system/files/publications/documents/english/sec-guide-to-proxy-brochures.pdf with more information about your voting rights as a shareholder.

PROPOSAL 1 - ELECTION OF THE COMPANY’S DIRECTORS

THE BOARD OF DIRECTORS

The Board is divided into three classes (each a “Class”). Each Class serves a three-year term.

At the 2023 Annual General Meeting, G. Manning Rountree, Mary C. Choksi, Weston M. Hicks and Steven M. Yi are nominated to be elected to Class II with a term ending in 2026. Of the nominees for election at the 2023 Annual General Meeting, Mr. Rountree and Ms. Choksi were previously elected by Shareholders. In 2022, the Compensation/Nominating & Governance Committee identified potential candidates that resulted in Mr. Hicks joining the Board of Directors in February 2023 and Mr. Yi being nominated for election at the 2023 Annual General Meeting. Mr. Hicks was identified by a third-party search firm. Mr. Yi was recommended by the Chief Executive Officer.

The Board recommends a vote FOR Proposal 1 which calls for the election of the 2023 nominees.

The director nominees, current members of the Board and terms of each Class are set forth below:

The Board is currently comprised of eight independent directors and the Chief Executive Officer. If Mr. Yi and the other director nominees are elected by shareholders at the 2023 Annual General Meeting, the board will have ten directors, of which eight will be independent.

Board Composition and Refreshment

The Company is committed to maintaining a Board with members from a variety of backgrounds to promote diverse, independent thinking. Diversity considerations are an important part of the director search process, and the Company believes that regularly enhancing and refreshing the makeup of the Board is important. In 2021, our Board committed to further expanding its diversity by adding a highly qualified and racially or ethnically diverse Board member by year-end 2022. The Board fulfilled that commitment prior to year-end 2022, increasing gender diversity from 29% to 33% and racial or ethnic diversity from 0% to 13%.

The Board remains committed to further expanding its diversity of skills, experience and background. If Mr. Yi and the other director nominees are elected by shareholders at the 2023 Annual General Meeting, the racial or ethnic diversity of the Board will increase to 20% and gender diversity will be 30%. With respect to independence, of nine current directors, eight are independent, with 100% independence on the Audit and Compensation/Nominating & Governance committees. If Mr. Yi and the other director nominees are elected by shareholders at the 2023 Annual General Meeting, the Board will have ten directors, of which eight will be independent. The Board regularly refreshes its membership to enhance the diversity of its skills, experience and background to effectively oversee the business as the Company evolves.

Director Skills and Qualifications

Our Board seeks Directors with a broad range of skills, experience and perspectives in order to ensure effective oversight of the Company’s strategies and risks. The Board believes its members must be willing and able to devote adequate time and effort to Board responsibilities. In evaluating director candidates, the Compensation/Nominating & Governance Committee evaluates attributes such as independence, integrity, expertise, breadth of experience, diversity, knowledge about the Company’s business and industry and ownership in the Company. The skills matrix below highlights our Board’s key skills and qualifications that are directly relevant to our business, strategy and operations. The Board reviews this matrix and the overall Board composition periodically in order to ensure the appropriate balance of diversity, knowledge and experience.

The lack of a checkmark for a particular item does not mean that the director does not possess that qualification, skill or experience, but rather the checkmark indicates that the item is a particularly prominent qualification, skill or experience that the director brings to the Board.

Board of Directors

Class I – Term Ending in 2025

Class II – To Be Elected to a Term Ending in 2026 

Class III – Term Ending in 2024

CORPORATE GOVERNANCE

We are committed to the ethical conduct of our business. This commitment is reflected in our corporate governance and in our corporate values and culture. Our corporate governance helps us to mitigate and manage risks by providing clear lines of oversight and responsibility for management and the Board. We review and seek to improve our corporate governance regularly.

The Company’s Corporate Governance Guidelines spell out our overall approach towards corporate governance. The Company also has a Code of Business Conduct that applies to all directors, officers and employees in carrying out their responsibilities to, and on behalf of, the Company. No waivers of the Code of Business Conduct were requested of, or granted by, the Board for any director or executive officer during 2022.

The Company’s Corporate Governance Guidelines and Code of Business Conduct are available at our website, www.whitemountains.com. These documents are available in print, free of charge, to any shareholder upon request.

The Board

The primary responsibility of the Board is to oversee and review management’s performance in order to advance the long-term interests of the Company and its shareholders. The day-to-day management of the Company, including preparation of financial statements and short-term and long-term strategic planning, is the responsibility of management.

In fulfilling their responsibility, directors must exercise common sense business judgment and act in what they reasonably believe to be in the best interests of the Company. Directors keep themselves informed by discussing matters with the CEO, other key executives and our principal external advisors, such as legal counsel, outside auditors and other consultants, by reading the reports and other materials that management sends them regularly, and by participating actively in Board and committee meetings. Directors are entitled to rely on the honesty and integrity of senior management and the Company’s outside advisors and auditors. However, it is the Board’s responsibility to establish that they have a reasonable basis for such reliance by ensuring that they have a strong foundation for trusting the integrity, honesty and undivided loyalty of the senior management team upon whom they are relying and the independence and expertise of outside advisors and auditors.

Mr. Davis, an independent director, serves as Chairman of the Board. At meetings of the Board, Mr. Davis presides over a separate session of non-management directors without Company management present. In addition to being led by an independent Board Chair, the Board is comprised of directors who, together, are knowledgeable and experienced in the Company’s business. The Board is satisfied that the current structure provides strong oversight of the Company’s affairs.

Shareholder Engagement

Shareholder engagement is of great importance to our Board and management team as a means to solicit feedback and to ensure accountability and responsiveness to our shareholders. We recognize the value in maintaining open lines of communication with our shareholders and consider our robust annual shareholder outreach program to be an important governance tool. In these meetings, we address any trends, topics or issues that participating shareholders wish to discuss with us. As part of our shareholder engagement efforts in 2022, we reached out to shareholders owning 71% of outstanding shares and met with all shareholders who accepted a meeting, who represented 32% of outstanding shares. Our Compensation / Nominating & Governance Committee Chair personally led discussions in meetings with shareholders representing 9% of outstanding shares.

These discussions centered around our business strategy, corporate governance (including Board diversity), executive compensation program composition of our board, and enhancements to our ESG disclosures. More specifically, we discussed our significant business achievements in 2022, our ESG practices, our continued focus on Board diversity, and our compensation philosophy and metrics. Our shareholders continued to express support for the changes we made to our compensation program in 2019, which included (i) making our annual bonus program for executive officers entirely formulaic with a pre-established, rigorous and quantifiable performance target relevant for our Company and industry and (ii) adopting share ownership guidelines for our executive officers. Our shareholders were supportive of our approach in 2022.

Our Annual Investor Meeting provides another opportunity for us to engage with our shareholders. The Company will hold its 2023 Annual Investor Meeting on Tuesday, June 6, 2023. Please refer to the Company’s website for further details.

Management and the Board recognize the value of direct shareholder input and take our shareholders’ views into account in managing or overseeing the Company. Shareholder feedback is regularly communicated to our full Board, and the input we received directly informed enhancements implemented to our executive compensation program in 2019, as well as enhanced disclosures relating to corporate governance, ESG and board diversity in our proxy statement.

Director Independence

The Board has determined that a majority of the Company’s current directors are independent, as defined in Section 303A of the New York Stock Exchange (“NYSE”) Listed Company Manual. Those directors determined to be independent are Messrs. Carlson, Davis, Gelston, Hicks and Tanner and Mmes. Choksi, Dillon and Shank. For a director to be independent, the Board must determine that the director has no relationship with the Company (other than being a director or shareholder of the Company or its subsidiaries) or has only immaterial relationships with the Company. The Company does not apply categorical standards as a basis for determining director independence. Accordingly, the Board considers all relevant facts and circumstances, on a case-by-case basis, in making an independence determination.

The Board notes no current relationships (other than being directors or shareholders) with Messrs. Carlson, Davis, Gelston, Hicks and Tanner or Mmes. Choksi, Dillon and Shank. In making its independence determinations, the Board would consider any such relationship in light of NYSE standards as well as the attributes it believes should be possessed by independent-minded directors. Those attributes include the relative impact of the transactions to the director’s personal finances, the perceived degree of dependence by the director or the Company upon the relationship or transactions continuing in the future and whether the transactions were on terms that were reasonable and competitive.

Board Meetings and Committees; Annual Meeting Attendance

During 2022, the following meetings of the Board were held: five meetings of the full Board, eight meetings of the Audit Committee, five meetings of the Compensation/Nominating & Governance Committee, four meetings of the Finance Committee and two meetings of the Self-Tender Pricing Committee. During 2022, each director attended more than 75% of the aggregate of: (1) the total number of meetings of the Board (held during the period for which he or she has been a director); and (2) the total number of meetings held by all committees of the Board on which he or she served.

It is White Mountains practice that all directors are invited to, receive materials for and generally attend all Committee meetings. In addition, each Committee Chair provides regular updates to the full Board regarding Committee activities. Directors are encouraged to attend the Annual General Meeting. All of the Company’s directors were in attendance at the 2022 Annual General Meeting, which was held on May 26, 2022.

Committees of the Board

Interlocks and Insider Participation

No member of the Compensation/Nominating & Governance Committee was an employee of the Registrant during the last fiscal year or has served as an officer of the Registrant.

Consideration of Director Nominees

General Criteria and Process for Selection of Director Candidates. Our Compensation/Nominating & Governance Committee regularly reviews the individual and collective skills and other attributes of Board members. In identifying and evaluating director candidates, the Compensation/Nominating & Governance Committee does not set specific criteria for directors. Under its Charter, the Committee is responsible for determining desired Board skills and evaluating attributes such as independence, integrity, expertise, breadth of business and life experience, diversity and knowledge about the Company’s business and industry and ownership interest in the Company. Directors must be willing to devote adequate time and effort to Board responsibilities. As set forth in the Company’s Corporate Governance Guidelines and its Charter, the Committee is responsible for recommending director candidates to the Board.

The Compensation/Nominating & Governance Committee has the authority to retain search firms to be used to identify director candidates. During 2022, a third-party search firm helped to identify Weston Hicks, our newest director. We inform any director search firm that may be retained of our preference to include highly qualified candidates who have diverse identities or backgrounds (including in respect of gender or gender identity, race, ethnicity or sexual identity) in the pool of potential candidates it presents for consideration by the Board.

Consideration of Diversity in Selection of Director Candidates. We believe that a variety of perspectives, opinions, backgrounds, business and life experiences and tenure among the members of the Board enhances the Board’s ability to perform its duties and effectively oversee the Company’s business. In the selection of director candidates, we welcome a diversity of skills, backgrounds, business and life experiences, identities and viewpoints. The Board enhanced its diversity in 2021 with the addition of two female directors (Mmes. Dillon and Shank) and one racially diverse director (Ms. Shank) and will further increase the Board’s skills, racial and ethnic diversity if Mr. Steven M. Yi is elected by shareholders at the 2023 Annual General Meeting.

Consideration of Director Candidates Nominated by Shareholders. The Company has not adopted a specific policy regarding consideration of director candidates from shareholders. Shareholders who wish to recommend candidates for consideration by the Committee may submit their nominations in writing to the Corporate Secretary at the address provided in this Proxy Statement. The Committee may consider such shareholder recommendations when it evaluates and recommends candidates to the Board for submission to shareholders at each annual general meeting. In addition, shareholders may nominate director candidates for election without consideration by the Committee by complying with the eligibility, advance notice and other provisions of our Bye-laws as described below.

Procedures for Nominating Director Candidates. Under the Company’s Bye-laws, nominations for the election of directors may be made by the Board or by any shareholder entitled to vote for the election of directors (a “Qualified Shareholder”). A Qualified Shareholder may nominate persons for election as directors only if written notice of such Qualified Shareholder’s intent to make such nomination is delivered to the Secretary not later than: (1) with respect to an election to be held at an annual general meeting, 90 days prior to the anniversary date of the immediately preceding annual general meeting or not later than 10 days after notice or public disclosure of the date of the annual general meeting is given or made available to Qualified Shareholders, whichever date is earlier, and (2) with respect to an election to be held at a special general meeting for the election of directors, the close of business on the seventh day following the date on which notice of such meeting is first given to Qualified Shareholders. Each such notice shall set forth: (a) the name and address of the Qualified Shareholder who intends to make the nomination and of the person or persons to be nominated; (b) a representation that the Qualified Shareholder is a holder of record of common shares entitled to vote at such meeting and intends to appear in person or by proxy at the meeting to nominate the person or persons specified in the notice; (c) a description of all arrangements or understandings between the Qualified Shareholder and each such candidate and any other person or persons (naming such person or persons) pursuant to which the nomination or nominations are to be made by the Qualified Shareholder; (d) such other information regarding each candidate proposed by such Qualified Shareholder as would have been required to be included in a proxy statement filed

pursuant to the proxy rules of the SEC had each such candidate been nominated, or intended to be nominated, by the Board; and (e) the consent of each such candidate to serve as a director of the Company if so elected.

Shareholder Communications

Shareholders, employees and others interested in communicating directly with the Board, any of the Board’s Committees or any individual member of the Board should write to the addressee, c/o the Corporate Secretary, at the address presented under “Available Information” (which appears on page 62).

Succession Planning

One of the top responsibilities of the Board is to ensure continuity in White Mountains’s senior leadership by overseeing the development of executive talent and planning for the efficient succession of the CEO and other senior executives. Among the responsibilities of the Compensation/Nominating & Governance Committee is to review, at least annually, the CEO’s short-term and long-term succession plans for the CEO and other senior management positions and report to the Board on succession planning. Our goal is to develop well-rounded and experienced leaders. The Company ensures that our executives have the necessary internal or external training and mentoring they need to develop professionally. Our high potential executives are regularly challenged with additional responsibilities and positioned to interact more frequently with the Board so Directors can get to know and assess them.

Risk Oversight

The Board, directly and through its Committees, plays an active role in the oversight of the Company’s risk management. The subject of risk management is a recurring agenda item, for which the Board regularly receives reports from management on capital, investments, and operations, including the risks associated with each and the steps management is taking to manage those risks. The Board discusses with management the Company’s business strategy, risk appetite and appropriate levels of risk, as well as considerations of ESG risks, such as the impact of climate change, human capital management and cybersecurity threats.

The Board’s committees are assigned oversight responsibility for particular areas of risk. For example, the Audit Committee receives a report, at least annually, on company-wide risks which considers operational, financial, legal, compliance, cyber and reputational risks, as well as climate risks and sustainability matters. The Compensation/Nominating & Governance Committee oversees risk related to executive compensation plans and implementation, corporate governance, succession planning, environmental stewardship, sustainability and corporate social responsibility. The Finance Committee oversees the risks related to managing the Company’s investment portfolio. Full Board meetings and individual Committee meetings are scheduled so as not to overlap and all directors are encouraged to attend all committee meetings, allowing for every director to participate and provide guidance regarding any risk concerns.

More information about the Company’s approach to risk management, including the primary frameworks used to assess risk and our approach to business continuity and the management of cybersecurity risks, is available on the ESG landing page on our Company website (www.whitemountains.com/esg/).

Enhancing Environmental, Social and Governance Practices and Disclosures

White Mountains strives to create superior growth in the Company’s intrinsic value per share over long periods of time.  In order to achieve this goal, and in order to steward our owners’ capital effectively, the Board and management are committed to sustainability and corporate responsibility. We have made this commitment an integral part of our culture and practices.

In 2020, with oversight from the Board of Directors, White Mountains embarked on a project designed to improve our ESG practices and disclosures. We identified ESG priorities that align with both our Company’s business strategy as well as industry and investor expectations. Our key areas of focus included (i) amending the Company’s investment policy to address ESG, (ii) adopting a climate change statement, (iii) formalizing the Board’s oversight of ESG matters, and (iv) further integrating climate-

related risks into our risk management practices. In response to feedback from shareholders, we also committed to improve the communication of our ESG practices by launching an ESG page within our corporate website.

Our ESG Practices

To strengthen our ESG practices, we undertook a comprehensive gap analysis to identify areas to improve that would align with our business strategy as well as industry and investor expectations. ESG topics were prioritized based on relevance, applicability and feasibility of implementation. The full Board had oversight of this process and final approval of the ESG focus areas and actions, which included:

“Climate change contributes to higher temperatures, sea level rise and more extreme weather events including droughts, heavy storms, wildfires and stronger hurricanes.  We do not manufacture products that produce carbon, nor do we otherwise meaningfully impact the environment through our operations. However, as the owner and operator of a diversified group of businesses in insurance, financial services and related sectors, we are exposed to risks that are exacerbated by climate change, in particular in our property and casualty insurance/reinsurance and municipal bond guaranty businesses.  Accordingly, in our risk management processes, we consider the potential impact of the effects of climate change. 

We also believe that we have an important role to play as a responsible corporate citizen on climate change matters. Our corporate philanthropy reflects our commitment to the environment.” 

More detailed information on the practices outlined above is available on the ESG landing page on our Company website (www.whitemountains.com/esg/).

Human Capital Management and Diversity & Inclusion

Our strength lies in our people, and we proactively support each employee’s well-being and development. Our Board receives periodic reporting on employee satisfaction and concerns and interacts with employees across our organization. We have an inclusive, team-oriented culture in which all employees are treated with respect. Under the guidelines of our Code of Business Conduct, we are firmly committed to providing equal employment opportunities. In our recruiting practices at our parent company, we require that a diverse slate of candidates be considered for every open position. We deeply value diversity of backgrounds, experiences and ideas, which we believe fosters more engaging discussions, stronger collaboration and better company performance. We invest in the professional development of our workforce and are committed to the long-term development of our workforce and the cultivation of our next generation of leaders. To support the advancement of our employees at the parent company, we endeavor to strengthen their qualifications by providing access to training in financial skills, effective communication and institutional knowledge. Our parent company mentoring program encourages new relationships and additional career support opportunities, and our Educational Assistance Program funds external professional development opportunities to further enhance job-related skills.

Corporate Social Responsibility

White Mountains is committed to the communities in which we live and work, and many of our employees actively support non-profit organizations in their respective communities. Their focus is mirrored by our corporate philanthropy efforts at our parent company, which include a charitable matching gift program, corporate support for environmental and social causes in the communities in which we operate, and partnerships with high quality organizations focused on issues of diversity & inclusion.

VOTING SECURITIES AND PRINCIPAL HOLDERS THEREOF

Voting Rights of Shareholders

As of April 1, 2023, there were 2,568,039 common shares outstanding. Shareholders of record of common shares shall be entitled to one vote per common share, provided that if, and so long as, the votes conferred by “Controlled” common shares (as defined below) of any person constitute ten percent (10%) or more of the votes conferred by the outstanding common shares of the Company, each outstanding common share comprised in such Controlled common shares shall confer only a fraction of a vote that would otherwise be applicable according to the following formula:

[(T divided by 10)-1] divided by C

Where: “T” is the aggregate number of votes conferred by all the outstanding common shares; and “C” is the number of votes conferred by the Controlled common shares of such person.

“Controlled” common shares in reference to any person means:

The limitations set forth above do not apply to any Shareholder which is a “Byrne Entity” (as defined below) for any matter submitted to the vote of Shareholders, except with respect to the election of directors. “Byrne Entity” means any foundation or trust established by John J. Byrne, Patrick Byrne, and any associate or affiliate of any of them (or any group of which any of them is a part), as defined under Section 13(d) of the United States Securities Exchange Act of 1934, as amended.

If, as a result of giving effect to the foregoing provisions or otherwise, the votes conferred by the Controlled common shares of any person would otherwise represent 10% or more of the votes conferred by all the outstanding common shares, the votes conferred by the Controlled common shares of such person shall be reduced in accordance with the foregoing provisions. Such process shall be repeated until the votes conferred by the Controlled common shares of each person represent less than 10% of the votes conferred by all common shares.

Security Ownership of Certain Beneficial Owners

To the knowledge of the Company, there was no person or entity beneficially owning more than 5% of the common shares outstanding as of April 1, 2023, except as shown below.

Security Ownership of Management

The following table sets forth, as of April 1, 2023, beneficial ownership of common shares by each director, the Named Executive Officers (as defined on page 32) and all other executive officers as a group:

EXECUTIVE COMPENSATION

FROM OUR COMPENSATION/NOMINATING & GOVERNANCE COMMITTEE

Dear Fellow Shareholders:

One of our most important responsibilities as the independent Compensation/Nominating & Governance Committee (the “CNG Committee”) is to structure our executive compensation program (i) to create strong alignment of interests with shareholders and (ii) to attract, retain and motivate talented executives who create long-term value for the Company and its shareholders.

We regularly seek feedback from our shareholders on our compensation practices. This year, we reached out to shareholders owning 71% of White Mountains’ outstanding shares and we met with all shareholders who accepted a meeting (32% of our outstanding shares). Mr. Philip Gelston, the CNG Committee Chair, led the discussions in several of these meetings. The feedback received during these meetings was valuable input for our continuous review and improvement of our compensation program.

Compensation Program Highlights:

In 2022, base salaries for Named Executive Officers remained capped at $500,000. Effective March 2023, we increased the cap from $500,000 to $600,000. This is the first increase since 2008 and was largely inflation driven. We continue to believe in offering fixed compensation that is below market.

We also continue to believe in paying for performance. In 2022, 92% of total CEO compensation (at target) was meaningfully “at risk” – dependent on Company performance or share price performance or both.

For all Named Executive Officers, the annual target bonus opportunity remains at 75% of salary.

For all Named Executive Officers, 50% of the annual LTIP grants take the form of three-year cliff-vested restricted stock and 50% take the form of three-year performance shares. For the past three years, we have set the performance target goal equal to the 10-year Treasury yield plus 700 basis points (which is our long-term equity return target). As yields have risen over the past several years, our targets have increased in lockstep.

History of Responsiveness to Shareholder Feedback on Compensation and Governance:

Following proactive shareholder engagement in recent years, White Mountains has:

Adopted a formulaic annual incentive program for our executive officers, with pre-established, rigorous and quantifiable performance targets that are relevant for our firm and industry

Enhanced proxy disclosure to include (i) a detailed, individual Board skills matrix that highlights our Board’s key skills and qualifications that are directly relevant to our business, strategy and operations and (ii) greater disclosure about diversity among Board members

Reaffirmed our commitment to increase gender and racial or ethnic diversity on our Board of Directors; we have nominated another highly qualified, ethnically diverse director

Enhanced our ESG practices by (i) amending the Company’s investment policy to address ESG, (ii) adopting a climate change statement, (iii) formalizing the Board’s oversight of ESG matters, (iv) further integrating climate-related risks into our risk management practices and (v) launching an ESG page on our website

The CNG Committee is committed to ensuring that our executive compensation programs and governance practices continue to drive long-term value creation. We welcome your continued feedback.

Sincerely,

The White Mountains Insurance Group Compensation/Nominating & Governance Committee

Philip A. Gelston, Chair   |   Morgan W. Davis   |   Margaret Dillon   |   Suzanne F. Shank

April 5, 2023

Compensation Discussion and Analysis

Executive Summary

Business Overview and 2022 Performance Highlights

White Mountains is engaged in the business of making opportunistic and value-oriented acquisitions of businesses and assets in the insurance, financial services and related sectors, operating those businesses and assets through its subsidiaries and, if and when attractive exit valuations become available, divesting to realize gains on their sale. Our principal focus is to grow adjusted book value per share (“ABVPS”) because we believe, based on the trading history of our stock, that over the long term our share price growth will parallel our growth in ABVPS (see chart and discussion on page 36). Since our IPO, including dividends, White Mountains has delivered 13% annualized growth in ABVPS and 12% annualized growth in market value per share.

We finished 2022 with book value per share of $1,457 and adjusted book value per share of $1,495, increases of 24% and 26% from the prior year, respectively. The main driver of growth was the gain on our sale of NSM, which added roughly $300 to ABVPS. Good operating results at our businesses also contributed to ABVPS growth, while the decline in MediaAlpha’s share price was a drag on results.

In 2022, BAM produced record levels of gross written premiums and member surplus contributions. Ark produced an 82% combined ratio while growing gross premiums 37% year-over-year. Kudu had a good all-around year, closing three new deployments and completing two value-adding sale transactions. We successfully completed a self-tender offer this past September, repurchasing roughly $459 million worth of shares. We finished 2022 with undeployed capital of roughly $0.9 billion.

Commitment to Ongoing Shareholder Engagement

As part of our ongoing commitment to better understand the views of our shareholders with respect to our business, governance, and compensation practices, we continued our investor outreach efforts in 2022. Over the past several years, feedback received from these discussions has helped guide refinements to our executive compensation programs and governance practices, as well as enhancements to our public disclosures. A summary of these efforts in 2022, feedback received and our history of responsiveness is included below:

Compensation Peer Group

As described in more detail below, the CNG Committee refers to a peer group as part of its evaluation of the Company’s compensation practices. We evaluate the executive compensation programs of these peers in terms of structure and variability of payouts in good and poor performance scenarios. We seek to structure our compensation program to be less fixed and more variable than peers. Importantly, we do not use this peer group to benchmark compensation. Unlike most of our insurance company peers, the primary responsibility of our parent company’s management is finding and executing opportunistic and value creating acquisitions and dispositions of operating businesses, rather than operating traditional insurance businesses (although our subsidiaries may operate insurance businesses). As a result, we believe benchmarking against the peer group could result in compensation that is not competitive for our talent pool. When recruiting and retaining talented professionals, we compete against private equity and investment banking opportunities more than other insurance companies, and our compensation practices must reflect this reality. The CNG Committee believes that our compensation structures closely align the financial interests of management with those of our shareholders and encourage appropriate, but not excessive, risk taking.

Following several refinements to our peer group for fiscal 2021, The CNG Committee made one change to the group to remove an acquired peer company. See page 35 for further details on our 2022 peer group.

Compensation Program Aligned with Company Performance

The current design of our compensation program consists of three primary elements: base salary, annual incentive bonus and long-term incentive compensation. Each element is structured with the primary goal of creating superior growth in our values per share over long periods of time. Highlights of our compensation program are as follows:

Elements and Structure

¹ The average of growth in adjusted book value per share (ABVPS) and growth in intrinsic value per share, which is the ABVPS including franchise value step-ups to reflect the fair value of certain subsidiaries carried at book value. See Annex A for a reconciliation of growth in ABVPS and growth in intrinsic value per share.  

We believe that the goal of creating superior growth in values per share over long periods of time is best pursued by utilizing a pay-for-performance program that closely aligns the financial interest of management with those of our shareholders while rewarding appropriate risk taking. We accomplish this by emphasizing variable long-term compensation, the value of which is tied to performance over a number of years rather than fixed entitlements. To illustrate, 86% of our CEO’s 2022 target total direct compensation was linked to long-term incentives, while approximately 8% was made up of base salary, and 6% linked to annual cash bonus opportunity at target.

Chief Executive Officer:

Other NEOs*:

Named Executive Officers

In this CD&A, we review the philosophy of White Mountains’s executive compensation program, the compensation process, the program’s elements, and the 2022 and 2023 compensation decisions for our Named Executive Officers:

Unless otherwise noted, the term Named Executive Officers (or “NEOs”) refers to the group of individuals listed in the above table; the term “CEO” refers to Mr. Rountree.

Business Overview, Significant Transactions, and Performance Highlights

White Mountains is engaged in the business of making opportunistic and value-oriented acquisitions of businesses and assets in the insurance, financial services and related sectors, operating these businesses and assets through its subsidiaries and, if and when attractive exit valuations become available, divesting to realize gains on the sale of these businesses and assets.

White Mountains finished 2022 with book value per share of $1,457 and adjusted book value per share of $1,495, increases of 24% and 26% from the prior year, respectively. The main driver of growth was the gain on our sale of NSM, which generated a net gain of $876 million and added roughly $300 to ABVPS.

In 2022, BAM produced record levels of gross written premiums and member surplus contributions. Ark produced an 82% combined ratio while growing gross premiums 37% year-over-year. Kudu had a good all-around year, closing three new deployments and completing two value-adding sale transactions. We successfully completed a self-tender offer this past September, repurchasing roughly $459 million worth of shares. We finished 2022 with undeployed capital of roughly $0.9 billion.

We believe the businesses we own today and our ability to deploy capital into further opportunistic and value-oriented acquisitions position us well for the future. The Company remains focused on creating shareholder value over the long term.

Shareholder Engagement and History of Demonstrated Responsiveness

Engaging with our owners is central to our commitment to good governance and critical to maintaining our strong corporate governance practices. Our 2022 shareholder outreach was led by the Board and senior management, including our CNG Committee chair, Mr. Philip Gelston, who provided a direct line of communication between the Board and our shareholders. This year, we reached out to shareholders representing approximately 71% of our outstanding shares and met with all shareholders who accepted meetings, representing 32% of our shares outstanding. Mr. Gelston personally led discussions in meetings with shareholders representing approximately 9% of our shares outstanding. Shareholder feedback received from these meetings was shared with the entire Board and help to inform our responsiveness actions.

The main topics in our engagement meetings were our business performance and outlook, capital deployment, capital management and self-tender, executive compensation practices and our corporate governance and company culture. More specifically, we discussed the NSM sale, Ark’s performance and exposures, MAX’s outlook and developments at BAM. Our shareholders were overwhelmingly supportive of our efforts to thoughtfully redeploy and return capital generated through the successful sale of NSM. Investors shared their appreciation of White Mountains’ shareholder value creation through our effective stewardship of capital, and we heard continued support for our enhanced sustainability disclosures and ESG landing page on our Company website.

The Company’s management and Board is committed to continuing its extensive shareholder outreach program.

Compensation Philosophy

Our executive compensation policies are designed with the primary goal of creating superior growth in our values per share over long periods of time. We believe that this goal is best pursued by utilizing a pay-for-performance program that closely aligns the financial interests of management with those of our shareholders while rewarding appropriate risk taking. We accomplish this by emphasizing variable long-term compensation, the value of which is tied to performance over a number of years rather than fixed entitlements (such as base salary, pensions, and employee benefits). To that end, the CNG Committee has established base salaries and target annual bonuses for our executives that tend to be lower than those paid by comparable property and casualty insurers and reinsurers, while granting the bulk of an executive’s target compensation as long-term incentive compensation. To illustrate, approximately 86% of our CEO’s 2022 target total direct compensation was linked to long-term incentives, while approximately 8% was made up of base salary and 6% was target annual cash bonus opportunity.

The following principles guide and inform the CNG Committee’s efforts to deliver a highly effective executive compensation program that drives shareholder value and fosters the attraction and motivation of key talent:

Compensation Setting Process

The CNG Committee is responsible for approving our compensation programs for executive officers, and it specifically approves all compensation for our executive officers and for any employee with target annual compensation in excess of $1.5 million. Our CEO annually presents to the CNG Committee his evaluation of our executives, their individual performance, achievements, and the contributions they made to the Company’s accomplishments over the past year, as well as over the most recent long-term incentive plan cycle. In connection with this evaluation, the CEO recommends to the CNG Committee appropriate compensation amounts for these executives. The CNG Committee evaluates these recommendations and also assesses the performance, responsibilities and contributions of the CEO, considers CEO succession plans, and sets the compensation of the CEO.

With the exception of significant promotions and new hires, compensation matters are usually addressed at the first meeting of the CNG Committee each year (typically late February), following the availability of financial results for the prior year and the current year’s financial plan. This allows us to determine the results of prior period grants and to set targets for the current year and newest long-term performance cycle. Performance cycles for long-term compensation typically run for three years beginning on January 1st of the year of grant.

Compensation Peer Group

When making new long-term incentive grants, the CNG Committee assesses the impact of different performance scenarios on potential realizable compensation. Further, in order to test our beliefs about the structure and variability of the awards we make, the CNG Committee annually reviews and considers a systematic analysis of the public compensation disclosures made by other property and casualty insurers and reinsurers that the CNG Committee considers to be peers.

Importantly, our compensation peer group is not used for benchmarking purposes, but rather to analyze whether our compensation programs are appropriately structured and to ensure they are less fixed and more variable than most other insurance and reinsurance peers.

Unlike most of our insurance company peers, the primary responsibility of our parent company’s management is finding and executing opportunistic and value creating acquisitions and dispositions of operating businesses, rather than operating traditional insurance businesses (although our subsidiaries may operate insurance businesses). As a result, we believe benchmarking against the peer group could result in compensation that is not competitive for our talent pool. When recruiting and retaining talented professionals, we compete against private equity and investment banking opportunities more than other insurance companies, and our compensation practices must reflect this reality.

In considering its analysis of compensation structure and variability, the Company uses a peer group of companies that reflects its traditional insurance competitors. The CNG Committee regularly evaluates the continuing appropriateness of this group and did so again during 2022. As a result of this review, Aspen Insurance was removed from the group, following its acquisition by Apollo Global Management.

The companies included in the analysis presented to the CNG Committee prior to it making compensation decisions in 2022 were:

The CNG Committee concluded that the peer analysis supported its view that the Company’s compensation programs are more variable than most other insurance and reinsurance peers, have fewer fixed elements of compensation and perquisites, and do not lead to significant rewards for poor performance. The CNG Committee believes that the compensation structures that have been developed for the Company closely align the financial interests of management with those of our shareholders and encourage appropriate, but not excessive, risk taking.

Compensation Best Practices

We maintain a number of compensation governance best practices which support our overarching compensation philosophy and are fully aligned with our compensation principles, as discussed in the following section. Our compensation practices also align with input we have received from shareholders.

Superior Track Record and the Alignment of Growth in ABVPS and Market Value Per Share

From our IPO in 1985 through year-end 2022, we have delivered 13% annualized growth in ABVPS and 12% annualized growth in market value per share to our shareholders. Importantly, as seen in the chart below, ABVPS and market value per share have generally moved in tandem over the last thirty-five years, despite short-term fluctuations. This is a core factor supporting the CNG Committee’s selection of incentive plan performance metrics that relate to growth in book value per share.

Compensation for 2022

The principal elements of compensation for our executives in 2022 - base salary, annual incentive bonuses and long-term incentive compensation - are discussed below.

2022 Target Annual Direct Compensation Mix

As discussed above under “Compensation Philosophy”, the Company’s compensation program emphasizes variable long-term incentive compensation, rather than fixed entitlements. Accordingly, we pay our executive officers salaries that we believe to be below market. In 2022, base salaries for Named Executive Officers remained capped at $500,000.

We provide annual bonus opportunities to our executive officers, which make up a small percentage of each NEO’s target total annual compensation – approximately 6% for our CEO, and 12% on average for the other NEOs in 2022 – as the bulk of our executive officers’ compensation opportunity is tied to long-term incentives. Each NEO participates in the annual bonus pool applicable to the parent holding companies. For 2022, the target bonus pool was $7.5 million for 57 employees.

Under our formulaic annual bonus program, the level of payout is determined by reference to the Company’s growth in CVPS, which is defined by the CNG Committee as the average of growth in ABVPS and growth in “intrinsic business value per share”, which is the ABVPS including franchise value step-ups to reflect the fair value of certain subsidiaries carried at book value. In choosing this metric for the annual bonus program, the CNG Committee recognized that this is the same metric as used in a portion of the Company’s long-term incentives (albeit for a different time period). The CNG Committee considered a number of other metrics but concluded that no other metric is as pertinent to our business as CVPS. CVPS is the metric that the Board and the management team focus on because it is linked to growth in book value per share metrics, which we believe is what ultimately drives growth in our share price. The 2022 annual bonus pool could range from 0% to 200% of target, based on the harvest scale of 4%-9%-14% growth in CVPS.

For our executive officers, the CNG Committee maintains the discretion to decrease the individual annual bonus payouts after the quantitative formula has been applied, however it does not have discretion to increase payouts. Our executive officers cannot receive more than the formulaic result.

For 2022, the NEOs had target annual bonuses of 75% of salary, which was unchanged from the prior year and is continued into 2023. Based on the Company’s performance of a 24% increase in CVPS in 2022, the CNG Committee awarded the NEOs bonuses of 200% of target. The below table excludes a $325,000 sign-on bonus that was paid to Mr. Caffrey upon joining the Company in March 2022, which was part of a $975,000 sign-on bonus payable in three equal annual installments. In the event Mr. Caffrey voluntarily terminates his employment prior to March 15, 2024, he must reimburse the Company for any portion of the sign-on bonus he has received.

3. Long-Term Incentive Compensation

Long-term equity awards generally consist of an equal mix of restricted shares and performance shares, rewarding long-term value creation and aligning executives’ interests with shareholders’ interests. Restricted shares are subject to a three-year cliff-vesting provision, instead of annual vesting, in order to promote retention that balances incentives to redeploy capital aggressively and to remain patient for good opportunities. The number of WTM common shares earned from a grant of performance shares can range from 0%-200% of target, based on after-tax annual growth in CVPS over the three-year performance cycle.

The CNG Committee selected performance metrics that relate to growth in book value per share because it continues to believe these metrics ultimately drive growth in our share price. The market value of our shares is not included as a direct measure of performance, but it determines the ultimate value of earned performance and restricted share awards.

From year-to-year when we make new long-term incentive grants, we typically adjust the target number of shares granted to individual employees to reflect the change in CVPS during the prior year, rather than focusing on changes in market values. This is consistent with our view that the change in book value per share and related metrics provides a better view of the change in value of the Company than metrics reflecting short-term market price fluctuations. In addition, we generally limit total annual share grants to employees to be equal to or less than 1% of the Company’s outstanding shares. For each of the past five grant cycles (from 2019-2021 to 2023-2025), we adhered to this guideline.

2022 Long-Term Incentive Grants: For the CEO and each of our other NEOs, the annual 2022 long-term incentive awards were allocated 50% as performance shares and 50% as restricted shares, consistent with prior years. With respect to the total grants made to employees across the Company, the CNG Committee granted 26,450 target shares for the 2022-2024 performance cycle, which represented a 2% decrease, year over year, in the number of shares granted. These grants totaled approximately 0.9% of the then outstanding shares. The restricted shares are subject to a three-year cliff vesting provision based on continuous service, in order to promote retention of key executive talent. The performance shares vest in a range of 0% - 200% of target, following a three-year performance period.

For the 2022-2024 performance period, the CNG Committee established a target of 9% annual growth in CVPS as the performance target that would result in the payout of 100% of the target performance shares. There would be no payout for annual growth of 4% or less, and annual growth of 14% or more would be required for a payout of 200%. In setting this performance scale, the CNG Committee’s goal was to set a performance target that was reasonable, but with an appropriate degree of stretch. Importantly, the 9% target was roughly equal to the Company’s long-term equity return target of the yield on the 10-year Treasury plus 700 basis points. In addition, the CNG Committee considered that the one-year performance scale for the 2022 annual bonus program was the same as the three-year average performance scale being set for the 2022-2024

performance shares. The Committee determined that this scale was appropriate due to the factors discussed above and their applicability over a longer time frame (which equates to aggregate growth of 12%-30%-48% over a three-year period).

A detailed breakdown of the 2022 grants is included in the table below:

In determining the amount of new long-term incentive compensation grants for 2022 for our NEOs, the CNG Committee assessed each executive’s scope of authority and ability to impact the success of the Company. Based on the CNG Committee’s general experience, familiarity with the Company and its compensation practices and the recommendation of the CEO (for NEOs other than himself), the CNG Committee established a grant level that it believed was appropriate to reflect each such executive’s expected contribution to the Company over the next performance cycle.

Mr. Campbell did not receive a long-term incentive grant in 2022, as he no longer receives long-term incentive grants from 2022 onwards, due to his pending retirement in February 2024.

Payout of 2020-2022 Performance Cycle: For the 2020-2022 performance cycle, long-term incentives were granted to the NEOs as follows: 50% as performance shares and 50% as restricted shares. For the performance shares, which matured at the end of 2022, 7% annual growth in CVPS was the performance target for a payout of 100% of the target performance shares. Annual growth of 2% or less would have resulted in no payout and annual growth of 12% or more would have resulted in a payout of 200%. At its meeting in February 2023, based on an average annual growth in CVPS of 15.6% during the 2020-2022 performance cycle, the CNG Committee confirmed that the payout that was earned was 200% of target.

2023 Compensation Actions

The CNG Committee increased the limit for executive officer base salaries from $500,000 to $600,000 effective in 2023, the first such increase since 2008. This change was made to create room for salary differentiation across the full management team and address inflationary pressures. Executive officers continue to have 75%-of-salary target bonus opportunities which remain unchanged from 2022. Their salary and bonus target levels continue to reflect the CNG Committee’s long-standing philosophy of linking a vast majority of executives’ compensation to long-term incentives in order to align their interests with those of our shareholders, as opposed to awarding high levels of fixed cash compensation.

Further, the design of our executive officers’ 2023 annual bonus plan will be similar to the plan in effect for 2022, with payouts tied to annual growth in CVPS and a harvest scale of 6%-11%-16% for threshold / target / maximum payout levels.

2023 Long-term Incentive Grants. In February 2023, the CNG Committee made new long-term incentive grants to the NEOs (other than Mr. Campbell) based on the same factors described above with respect to grants made in 2022 and allocated 50% as performance shares and 50% as restricted shares. With respect to the total grants made to employees across the Company, the CNG Committee granted 21,790 target shares for the 2023-2025 performance cycle, which represents an 18% decrease, year over year, in the number of shares granted. These grants totaled approximately 0.8% of the then outstanding shares. 

The CNG Committee set a performance target of 11% annual growth in CVPS, which was slightly above the Company’s long-term equity return target of the yield on the 10-year Treasury plus 700 basis points. The CNG Committee determined that 11% annual growth in CVPS is an appropriately challenging target for a payout of 100% of the target performance shares for the 2023-2025 performance cycle. Annual growth of 6% or less would result in no payout, and annual growth of 16% or more would result in a payout of 200%.

The CNG Committee believes this target and scale properly incentivize management to manage our businesses efficiently, without taking inappropriate risks.

Share Ownership Guidelines for Executive Officers

The CNG Committee has established share ownership guidelines for our executive officers. According to the guidelines, our CEO and EVPs are required to hold Company shares with a value of 10x salary, while other executive officers are required to hold Company shares with a value of 3x salary. Shares received upon vesting must be held until the executive is in compliance with the guideline. Unvested restricted shares will count toward satisfaction of the guideline, while unvested performance shares will not count. As of December 31, 2022, all NEOs were in compliance with the guidelines.

Clawback Policy

The Company has adopted a clawback policy applicable to bonuses and long-term incentive awards. If the Company restates any financial statement included in an SEC filing as a result of an employee’s misconduct, the Board may, without prejudice to any other remedies available to the Company, seek reimbursement of any bonus or long-term incentive award received by such person that relates in whole or in part to any period for which such financial statements were restated. If the misconduct involved fraud, then in addition to other actions the Board will mandatorily seek such reimbursement.

The Company is in the process of revising its clawback policy to comply with recently enacted SEC and stock exchange rules at the time such rules become effective.

Other Elements of Compensation

Retirement Benefits

We have no active U.S. defined benefit pension plans. Benefit accruals under all our U.S. qualified defined benefit pension plans and all our U.S. supplemental defined benefit pension plans were frozen for all employees in 2002.

Our employees may participate in our qualified 401(k) plans and eligible employees can participate in a qualified employee stock ownership plan. We do not provide supplemental retirement benefits to any employees in connection with these plans.

Perquisites

We review the perquisites that our senior management receives. The primary perquisite is limited personal use of corporate aircraft.

We allow our NEOs to use our corporate aircraft from time to time for personal reasons. The aggregate incremental cost to the Company is included, for proxy reporting purposes, as compensation to the NEO. For tax purposes, we comply with IRS regulations. We do not “gross-up” our NEOs for their taxes associated with perquisites, including with respect to personal use of our aircraft.

Our NEOs also participate in our benefit plans on the same terms as our other employees. These plans include medical and health insurance, company paid life insurance and charitable gift matching.

Certain Board Fees

Our NEOs do not receive director fees for serving on the Company’s board of directors or for serving on the boards of our wholly-owned or majority-owned subsidiaries. However, those NEOs who serve on the boards of other companies in which we have a minority interest may receive director fees from those companies. We consider those board fees when evaluating the compensation of our NEOs.

Compensation Arrangement for Mr. Caffrey

We have no long-term employment agreements with our NEOs although, from time to time, we have entered into short-term arrangements with newly hired executives governing their compensation and severance during a period of up to their first three years with the Company.

On December 2, 2021, the Company announced that Mr. Caffrey would become its Executive Vice President and Chief Financial Officer on March 1, 2022. In connection with Mr. Caffrey’s hiring, the Company agreed to the following terms, which the CNG Committee believes were reasonably negotiated and aligned with market practices:

Severance Agreements; Change in Control

Severance benefits, if any, for our NEOs are determined by the CNG Committee in its sole discretion. Executive officers of our operating subsidiaries participate in the severance plans, if any, generally applicable at those companies.

If any of our most senior executives decide to retire, in order to enable the Company to ensure a smooth transition, to receive a non-compete/non-solicit from the executive and to retain access to valuable knowledge, talents and relationships, our general practice has been to enter into arrangements that would permit the executive to earn some or all of such executive’s long-term incentive compensation then outstanding.

We have no standalone change in control agreements with our NEOs. However, under our long-term incentive plans, if a change in control of the Company (or a business unit, as applicable) were to occur, certain events, such as involuntary or constructive employment termination or amendments to our incentive plans which are materially adverse to its participants, may cause stock options to become fully exercisable, restricted shares to become immediately vested and performance shares and performance units to become payable in full or in part. Our plans do not provide for tax gross-ups for excess parachute payments that may result from a change in control.

Compensation/Nominating & Governance Committee Report

The Compensation/Nominating & Governance Committee of the Company has reviewed and discussed the Compensation Discussion and Analysis required by Item 402(b) of Regulation S-K with management and, based on such review and discussions, the Compensation/Nominating & Governance Committee recommended to the Board that the Compensation Discussion and Analysis be included in this Proxy Statement.

Philip A. Gelston, Chair

Morgan W. Davis

Margaret Dillon

Suzanne F. Shank

Summary Compensation Table

The following table presents compensation in 2022, 2021 and 2020 for the Company’s CEO, CFO, former CFO and its two other most highly compensated executive officers (collectively, the “Named Executive Officers”):

All Other Compensation

The following table presents a breakout of “All Other Compensation” included in the Summary Compensation Table for 2022, 2021 and 2020:

Grants of Plan-Based Awards

The following table presents grants of plan-based awards granted, except as otherwise noted, under the White Mountains Long-Term Incentive Plan (the “WTM Incentive Plan”) to the Named Executive Officers that received such awards during 2022:

Outstanding Equity Awards at Fiscal Year-End

The following table presents outstanding equity awards under the WTM Incentive Plan, except as otherwise noted, to the Named Executive Officers as of December 31, 2022:

Option Exercises and Stock Vested

The following table presents stock awards that vested in 2022 for each of the Named Executive Officers. No option awards were exercised by the Named Executive Officers during 2022.