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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.          )

LETTER FROM THE BOARD OF DIRECTORS

FROM OUR BOARD OF DIRECTORS

Dear Fellow Shareholders:

2019 was a strong year for our Company driven by good operating results in our main businesses and strong absolute investment returns.  Our share price increased 30%.  We also deployed $435 million into businesses during the year, and ended 2019 with undeployed capital at $1.0 billion.  This level of undeployed capital reflects management’s thoughtful and patient redeployment and return of capital over the past several years following sales of a number of our large businesses between 2015 and 2017 that generated $4 billion in proceeds.  Your Board believes that this patient approach to redeployment will serve owners well in the years to come.

Strong Financial Performance

We finished 20192021 with book value per share of $1,024$1,176 and adjusted book value per share of $1,018, increases$1,190, decreases of 14%7% and 15%6% from the prior year.year, respectively. Excluding the gain from themark-to-market decline in our investment in MediaAlpha, transaction in February 2019, BVPS and ABVPS each grew 8%.  We focus management on growing ABVPS because we believe that, in the long term, growth in marketadjusted book value per share will followincreased 4% for the year, reflecting positive results from our operating businesses.

Ark produced good underwriting results in a heavy catastrophe year, while growing full year premiums 77%. At BAM, investor demand for bond insurance remained strong, and BAM insured a record $15.6 billion of par in the primary market. NSM finished 2021 with new highs for pro forma controlled premiums and pro forma adjusted EBITDA. Likewise, Kudu produced strong growth in ABVPS.  In 2019, our one-year total shareholder return was 30.2%. Each of our main operating businesses performed well this year,adjusted EBITDA and our total investment portfolio returned 20.4% (15.5% excludingcompleted five acquisitions during the gain from the MediaAlpha transaction).  A very satisfying result.year.

Execution of Our Business StrategyThe businesses we own today position us well for the future. As is the White Mountains “way,” we continue to prospect for acquisition opportunities, via our “platform business” and at the parent company.

During 2019, your Company made good progress on capital deployment, putting $435 million to work.  Three significant deals emerged from our platform companies: (i) Embrace, a pet insurance MGA acquired by NSM, (ii) the acquisitionEnhancement of NSM’s collector car renewal rightsESG Practices and (iii) our buyout of Oaktree’s 50% interest in Kudu.  At the parent company, we closed the Elementum transaction and strengthened our deal pipeline considerably.Disclosures

Thoughtful ApproachWhite Mountains seeks to create superior growth in the Company’s intrinsic value per share over the long term. In order to achieve this goal, and in order to steward our owners’ capital effectively, the Board Composition with a Demonstrated Commitmentand management are committed to Refreshment

Assustainability and corporate responsibility. We have made this commitment an integral part of our ongoing commitment to creating a balancedculture and effective Boardpractices. In 2021, with diverse viewpoints, skills, and deep industry expertise related to our Company strategy, Peter Carlson joinedoversight from the Board in 2019. Pete brings over thirty years of accountingDirectors, White Mountains aligned our ESG priorities with both our Company’s business strategy as well as industry and audit experience ininvestor expectations. We significantly enhanced our ESG practices by (i) amending the insurance industry.  He isCompany’s investment policy to address ESG, (ii) adopting a climate change statement, (iii) formalizing the former Executive Vice PresidentBoard’s oversight of ESG matters, and COO of Brighthouse Financial and(iv) further integrating climate-related risks into our risk management practices. In response to feedback from shareholders, we also improved the former Executive Vice President and CAO of MetLife. Our Board has a robust refreshment process and, since 2017, four new independent directors have joined the Board, replacing three long-serving directors. Average tenure now stands at seven years, and women comprise 25%communication of our members.ESG practices by launching an ESG page on our website.

Ongoing Dialogue with Shareholders Through Proactive Engagement

Engaging with our shareholders remains a high priority.  Over the last year, members of the Board and management reached out to shareholders owning 72% of White Mountains’Mountains’s shares outstanding shares and met with all of those shareholders who requested meetings,accepted a meeting, who represented 26%19% of our shares outstanding. Over the past several years, feedback received from these discussions has helped guide changes to our executive compensation program and furtherto enhance our disclosures about the skills and areas of expertise of our Board the Board’s oversight ofand our risk management and our human capital management initiatives.  In this year’s proxy statement, we have included apractices in general. This year our discussions with shareholders focused on our business strategy, corporate governance, the composition of our Board skills matrix, enhancedand enhancements to our disclosure around Board oversight of ESG and added a section on human capital management.disclosures.

In 2021, in response to shareholder feedback, the Board committed to further expanding its diversity by adding a highly qualified and racially or ethnically diverse Board member by year-end 2022. During the year, the Board fulfilled its commitment, increasing gender diversity from 29% to 38% and racial or ethnic diversity from 0% to 13%. The global pandemicBoard is challenging allcommitted to refreshing its membership regularly in order to enhance the diversity of us in 2020, but ourits skills, experience and background and to effectively oversee the Company as it evolves.

Our core principles serveserved us equally well in times of calm and times of uncertainty.  We wish you well2021, as you manage through these turbulent times.we continued to meet the challenges posed by the global pandemic. It is a privilege to serve as your Board, and we greatly value highly your support of White Mountains.

Sincerely,

The White Mountains Insurance Group Board of Directors

Class I – To Be Elected to Class III and to a Term Ending in 2024

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Class II – To Be Elected to a Term Ending in 2023

Class III – To Be Elected to a Term Ending in 2023

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Class III – Term Ending in 20212024

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Table of ContentsCORPORATE GOVERNANCE

CORPORATE GOVERNANCEWe 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 2019.2021.

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.  The primary responsibility of the Board is to oversee and review management’s performance of these functions in order to advance the long-term interests of the Company and its shareholders.

In fulfilling thistheir 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 that, 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. Building onWe recognize the value in maintaining open lines of communication with our 2018 engagement efforts, asshareholders 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 2019 shareholder engagement efforts in 2021, we reached out to shareholders owning 72% of outstanding shares and met with all shareholders who requested meetings,accepted a meeting, who represented 26%19% of outstanding shares. Our Compensation / Nominating & Governance Committee Chair personally led discussions in meetings with shareholders representing 13% of outstanding shares, which were all meetings where her participation was requested.

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These discussions centered around our business strategy, corporate governance (including Board diversity), executive compensation program composition of our board, and board oversight of risk management.enhancements to our ESG disclosures. More specifically, we discussed our significant business achievements in 2021, the evolution of our ESG practices, our progress 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, our continued board refreshment with the appointment in 2019 of our newest independent director, insurance industry veteran Peter Carlson, and our environmental and sustainability practices.  The 2019 changes to our compensation program were towhich included (i) makemaking 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) adopt adopting

share ownership guidelines for our executive officers. Our shareholders were overwhelmingly supportive of our executive compensation programs, including the performance metrics usedapproach in our 2019 annual bonus program and 2019-2021 long-term incentives, and our patient capital redeployment efforts.2021.

Our Annual Investor Meeting provides another opportunity for us to engage with our shareholders. The Company will hold its 2022 Annual Investor Meeting on Friday, June 10, 2022. 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 the expanded disclosuredisclosures relating to corporate governance, ESG and board diversity in this year’sour proxy statement (e.g., Board’s Role in ESG Oversight and Director Skills and Qualifications with an individual skills matrix).

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, Smith and Tanner and Mmes. Choksi, Dillon and Holiday.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, Gelston Smith and Tanner or Mmes. Choksi, Dillon and Holiday.Shank. The Board notes a relationship with Mr. Davis, as disclosed herein under “Director Compensation”, that it concluded was immaterial and did not impair his independence. In making its independence determinations, the Board considers all such relationships 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 2019,2021, the following meetings of the Board were held: fourfive meetings of the full Board, nineeight meetings of the Audit Committee, five meetings of the Compensation/Nominating & Governance Committee one meeting of the Performance Compensation Subcommittee and four meetings of the Finance Committee. During 2019,2021, 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 annual meetings.the Annual General Meeting and our Annual Investor Meeting. All of the Company’s directors were in attendance at the 20192021 Annual General Meeting, which was held on May 23, 2019.27, 2021, and the 2021 Annual Investor Meeting, which was held on June 4, 2021.

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Committees of the Board

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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 55)56).

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 also discusses with management the Company’s business strategy, risk appetite and appropriate levels of risk.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.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.

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TableMore 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 Contentscybersecurity 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 invests with the goal of creating superior growth in the Company’s intrinsic value per share over the long term.  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 Roleoversight 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 Oversightlanding 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.

Throughout the unique challenges of 2020 and 2021, our commitment to the health and safety of our employees and their families has been our guiding priority. To support our employees during this time, we expanded and encouraged remote work, introduced protocols and practices that emphasized employee well-being, regularly solicited feedback from our employees and ensured frequent senior leadership communication.

Corporate Social Responsibility

The BoardWhite Mountains is responsible for overseeingcommitted to the Company’s managementcommunities in which we live and work, and many of ESG matters.  Following our core operating principle of Thinking Like Owners, we maintain robust and owner-focused corporate governance practices.  With respect to environmental matters, while our business operations do not have a large physical footprint, we strive to make meaningful contributions towards protecting the environment and contributing to our local communities.  As to sustainability, the Board oversees the Company’s corporate culture and reinforces the importance of promoting a respectful and diverse work environment that enables our employees to be productiveactively 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 feel valued.  We focus on building long-term value for our owners by building enduring partnerships with the management teams and our partners in our various businesses andsocial causes in the communities in which we operate.  The Board is proudoperate, and partnerships with high quality organizations focused on issues of the Company’s efforts, which can generally be broken down into four main categories:diversity & inclusion.

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VOTING SECURITIES AND PRINCIPAL HOLDERS THEREOF

Voting Rights of Shareholders

As of April 1, 2020,2022, there were 3,128,6442,994,162 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:

(1)all common shares directly, indirectly, or constructively owned by such person within the meaning of Section 958 of the Internal Revenue Code of 1986, as amended, of the United States; and

(2)all common shares directly, indirectly, or constructively owned by any person or “group” of persons within the meaning of Section 13(d)(3) of the Exchange Act and the rules and regulations promulgated thereunder; provided that this clause (ii) shall not apply to (a) any person (or any group that includes any person) that has been exempted from the provisions of this clause or (b) any person or group that the Board, by the affirmative vote of at least seventy-five percent (75%) of the entire Board, may exempt from the provisions of this clause.

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.

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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, 2020,2022, except as shown below.

(a)Information as of February 28, 2020, based on Schedule 13G/A filed with the Securities and Exchange Commission on March 6, 2020, by and on behalf of The Vanguard Group.

(b)Information as of December 31, 2019, based on Schedule 13G/A filed with the Securities and Exchange Commission on January 27, 2020, by and on behalf of Wellington Management Group, LLP.

Security Ownership of Management

The following table sets forth, as of April 1, 2020,2022, beneficial ownership of common shares by each director, the Named Executive Officers (as defined on page 26)28) and all other executive officers as a group:

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EXECUTIVE COMPENSATION

FROM OUR COMPENSATION/NOMINATING & GOVERNANCE COMMITTEE

Dear Fellow Shareholders:

One of our most important mandatesresponsibilities as the independent Compensation/Nominating & Governance Committee (the “CNG Committee”) is to structure our executive compensation programs and governance practices to create close alignment with our shareholders’ interests, while continuing to attract and retain talented executives to execute on our Company’s strategy and create long-term value.

To that end, we regularly seek feedback from our shareholders on our compensation practices and, as appropriate, make refinements that we believe enhance our programs. FollowingWe believe our 2019responsiveness to that input is reflected in our 2021 Say-on-Pay vote, which received nearly 94% support,98% support. This year, we reached out to shareholders owning approximately 72% of White Mountains’ outstanding shares and met with all shareholders who requested meetings,accepted a meeting, who represented 26%19% of our shares outstanding. Ms. Edith Holiday,Mr. Philip Gelston, the CNG Committee chair, personally led discussions in meetings with shareholders representing 13%several of our shares outstanding, which were all meetings in which her participation was requested.these meetings. The feedback received during these meetings was extremely valuable as we evaluatefor our evaluation of our compensation programs for potential improvements in structure or disclosure.

20192021 Compensation Program Highlights:

ØBase salaries were held flat for all Named Executive Officers

ØAnnual percent-of-salary target bonus opportunities were held flat for all Named Executive Officers

ØOver 92%History of total target 2019 CEO compensation was linked to Company or share performance and therefore meaningfully “at-risk”

Changes in ResponseResponsiveness to Shareholder Feedback on Compensation and Governance:

ØIntroduced 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 – see page 32

ØEstablished share ownership guidelines for our executive officers, set at 10x base salary for our CEO and Executive Vice Presidents, and at 3x base salary for other executive officers – see page 35

White Mountains remains in a transitional period marked by thoughtful and patient redeployment of undeployed capital generated from sales of businesses in recent years, and theThe CNG Committee remainsis committed to ensuring that our executive compensation programs and governance practices continue to motivate long-term value creation. We believe the actions highlighted above arewe have been responsive to our shareholders’ input, and we welcome your continued feedback.

Sincerely,

The White Mountains Insurance Group Compensation/Nominating & Governance Committee

Edith E. Holiday, Chair

Morgan W. Davis

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

April 7, 20206, 2022

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Compensation Discussion and Analysis

Executive Summary

Business Overview and 20192021 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 30)32). Since our IPO, including dividends, White Mountains has delivered 13% annualized growth in ABVPS and 12%11% annualized growth in market value per share. Having sold off a number of significant businesses from 2015-2017, which generated $1.4 billion in transaction gains and left us with $3.1 billion of pro forma undeployed capital, we remain in a transitional period as we continue to work to thoughtfully redeploy and distribute the proceeds of those transactions.

2019 was a strongWe finished 2021 with book value per share of $1,176 and adjusted book value per share of $1,190, decreases of 7% and 6% from the prior year, for our Company driven by good operating resultsrespectively. Excluding the mark-to-market decline in our main businesses and strong absolute investment returns, which led to a strong one-year total shareholder return of 30.2%.  Excludingin MediaAlpha, adjusted book value per share increased 4% for the gainyear, reflecting positive results from the MediaAlpha transaction in February 2019, we grew ABVPS by 8.1% and our total investment portfolio returned 15.5%.operating businesses.

In 2019,2021, Ark produced good underwriting results in a heavy catastrophe year, while growing full year premiums 77%. At BAM, investor demand for bond insurance remained strong, and BAM insured a record $15.6 billion of par in the primary market. NSM finished 2021 with new highs for pro forma controlled premiums and pro forma adjusted EBITDA. Kudu produced strong growth in adjusted EBITDA and completed five acquisitions. We also smoothly effected leadership succession in our senior management team and appointed and on-boarded two independent directors, Mmes. Shank and Dillon, who reinforce and expand the Board’s skill set. Finally, we redeployed $435 million into businesses, following $332 million in capital deployments in 2018,successfully navigated year two of the COVID-19 pandemic with balance and we ended the year with undeployed capital of $1.0 billion.  We expectsensitivity, supporting our returns to continue to normalize and revenues to grow as we finish redeploying and distributing this capital.employees while resuming in-office work.

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 have continued our investor outreach efforts in 2019.2021. 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 disclosure.disclosures. A summary of these efforts in 2019,2021, feedback received and our history of responsiveness is included below:

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Elements and Structure 

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We believe that the goal of maximizing shareholder value 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%88% of our CEO’s 20192021 target total direct compensation was linked to long-term incentives, while 8%approximately 7% was made up of base salary, and 6%5% linked to annual cash bonus opportunity at target.

Chief Executive Officer:

Other NEOs:

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 20192021 and 20202022 compensation decisions for our named executive officers:Named Executive Officers:

Unless otherwise noted, the term named executive officersNamed Executive Officers (or “NEOs”) refers to the group of the five individuals listed in the above table,table; the term “CEO” refers to Mr. Rountree,Rountree; and the term “CFO” refers to Mr. Campbell and the term “CNG Committee” refers to the Compensation/Nominating & Governance Committee of the Board of Directors of White Mountains.through February 28, 2022.

Business Overview, Significant Transactions, in 2015-2017 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.

From 2015-2017, White Mountains soldfinished 2021 with book value per share of $1,176 and adjusted book value per share of $1,190, decreases of 7% and 6% from the prior year, respectively. During the year, MediaAlpha’s share price declined from $39.07 to $15.44, giving back a numberportion of its businesses—Sirius, Symetra, Tranzactthe gains created in 2020. This decline was a key driver of White Mountains financial results in 2021. Excluding this decline, adjusted book value per share increased 4% for the year, reflecting positive results from our operating businesses.

In 2021, Ark produced good underwriting results in a heavy catastrophe year, while growing full year premiums 77%. At BAM, investor demand for bond insurance remained strong, and OneBeacon—as buyers made compelling offers that resulted in roughly $1.4BAM insured a record $15.6 billion of transaction gainspar in the primary market. NSM finished 2021 with new highs for pro forma controlled premiums and drovepro forma adjusted EBITDA. Kudu produced strong growth in ABVPS.  As a resultadjusted EBITDA and completed five acquisitions. We also smoothly effected leadership succession in our senior management team and appointed and on-boarded two independent directors, Mmes. Shank and Dillon. Finally, we successfully navigated year two of these sales, the Company is in a transitional period as management works to intelligently redeployCOVID-19 pandemic with balance and distribute the transaction proceeds.  As of May 2017, on a pro forma basis for theOneBeacon sale, the Company had undeployed capital of $3.1 billion on a capital base of $4.2 billion.  In addition, after the sales, the Company generated much lower revenues than before the sales, and the high level of undeployed capital implied a low single digit go-forward rate of growth in ABVPS. As undeployed capital continues to be deployed or distributed, we expect returns to normalize and revenues to grow.

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In 2019, we continued to make good progress and deployed $435 million.  Three significant deals emerged fromsensitivity, supporting our platform companies: (i) Embrace, a pet insurance MGA acquired by NSM, (ii) the acquisition of NSM’s collector car renewal rights and (iii) our buyout of Oaktree’s 50% interest in Kudu.  As of December 31, 2019, undeployed capital was down to $1.0 billion. In 2019, excluding the gain from the early 2019 MediaAlpha transaction, ABVPS and CVPS grew by 8.1% and 9.1%, respectively.  These results outperformed their respective targets for the year, which were set rigorously by the CNG Committee above the prior period targets.  In addition, for the 2017-2019 performance cycle, the average annual growth in ABVPS and CVPS was 8.9% and 7.9%, respectively.employees while resuming in-office work.

The Company remains focused on creating shareholder value, while targeting redeployment in its areas of expertise: primarily insurance, broader financial services and adjacent sectors.businesses we own today position us well for the future. The Company remains value-oriented, opportunistic, and highly flexible.focused on running our businesses efficiently and creating shareholder value.

Shareholder Engagement and 2019 Compensation Program ChangesHistory of Demonstrated Responsiveness

Engaging with our owners is central to our commitment to good governance and critical to maintaining our strong corporate governance practices. Building on our 2018 engagement efforts, our 2019Our 2021 shareholder outreach was led by the Board and senior management, often including our CNG Committee chair, Ms. Edith Holiday,Mr. Philip Gelston, leading the discussion and providing a direct line of communication between the Board and our shareholders. FollowingIn our 20192021 Say-on-Pay vote, whichwe received nearly 94% support,98% support. This year, we reached out to shareholders representing approximately 72% of our outstanding shares and met with all shareholders who requestedaccepted meetings, who represented 26%19% of our shares outstanding. Ms. HolidayMr. Gelston personally led discussions in meetings with shareholders representing approximately 13% of our shares outstanding, which were all meetings in which her participation was requested.outstanding. Shareholder feedback received from these meetings was shared with the entire Board and helpedhelp to inform the CNG Committee’s thinking as it evaluated our compensation programs to continue to motivate and reward our executive officers for strong performance in executing our strategic transformation, while also taking into account shareholders’ views on the structure of our compensation programs.responsiveness actions.

The main topics in our engagement meetings were our current business strategy, corporate governance (including Board diversity), executive compensation program, and boardpractices, Board oversight of risk management.management, and ESG practices and disclosure. More specifically, we discussed the changes we made to our compensation program in 2019, our continued board refreshmentbusiness developments with the appointmentArk, NSM, Kudu, MediaAlpha, and BAM businesses, our addition of two members to the Company’s Board in 2019 of2021 (Mmes. Shank and Dillon), our newest independent director, insurance industry veteran Peter Carlson,recently enhanced ESG practices and disclosures, and our environmental and sustainability practices.executive compensation program. Our shareholders were overwhelmingly supportive of our successful capital redeployment efforts, Board refreshment, approach to ESG disclosure and oversight, and executive compensation programs, including the performance metrics used in our 2019 annual bonus program and 2019-2021 long-term incentives, and our patient capital redeployment efforts.programs. Shareholder feedback is regularly communicated to our full Board, and the input we received previously directly informedinfluenced the enhancements implementedwe made to our proxy disclosure, ESG disclosure, and executive compensation program in 2019 (summarized below), as well as the expanded disclosure in this year’s proxy statement (e.g., Board’s Role in ESG Oversight and Director Skills and Qualifications with an individual skills matrix).

2019 executive compensation program changes in response to shareholder feedback were:

ØIntroduced 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 – see page 32 for additional detail

ØEstablished share ownership guidelines for our executive officers, set at 10x base salary for our CEO and Executive Vice Presidents, and at 3x base salary for other executive officers – see page 35 for additional detailprogram.

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

Compensation PhilosophyPhilosophy

Our executive compensation policies are designed with the primary goal of maximizing shareholder value 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

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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’sexecutive's target compensation as long-term incentive compensation. To illustrate, 86%88% of our CEO’s 20192021 target total direct compensation was linked to long-term incentives, while 8%approximately 7% was made up of base salary and 6%5% 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: