WHITE MOUNTAINS INSURANCE GROUP LTD
For the period ended May 21, 2026. Filed Apr 1, 2026.
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What shareholders are asked to vote on at a company's meeting. It is where to find what directors and top executives are paid, and who owns the most shares.
May 21, 2026 · Filed Apr 1, 2026
Contents
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.
| Meeting Information and Availability of Proxy Materials | |
|---|---|
| Date and Time: | May 21, 2026 at 8:00 a.m. Atlantic Time |
| Place: | Rosewood Bermuda Hotel, 60 Tucker’s Point Drive, Hamilton Parish, Bermuda |
| Record Date: | March 30, 2026 |
This Proxy Statement and the accompanying proxy card are being sent to shareholders on or about April 16, 2026.
| Voting Matters and Board Recommendations | ||
|---|---|---|
| Matter | Our Board’s Recommendation | |
| Proposal 1 | Election of four directors to Class II with terms ending in 2029 | For |
| Proposal 2 | Approval of the advisory resolution on executive compensation | For |
| Proposal 3 | Approval of the appointment of PwC as the Company’s Independent Registered Public Accounting Firm for 2026 | For |
| How to Vote | |
|---|---|
| Even if you plan to attend the 2026 Annual Meeting of Members in person, we encourage you to vote in advance of the meeting. Make sure to have your proxy card or voting instruction form in hand and follow the instructions. Participants who hold shares in a brokerage account, an employee benefit plan, or through a nominee will need to follow instructions on their proxy card, which may include options to vote their shares by telephone or over the internet. You can vote in one of three ways: | |
| Record Holders | Beneficial Owners |
| Vote via the internet | Follow the instructions set forth on the voting instruction form provided by your broker with these proxy materials. |
| ● Go to www.envisionreports.com/WTM | |
| Vote by telephone | |
| ● Call toll free 1-800-652-VOTE (8683) within the USA, US territories and Canada | |
| Vote by mail | |
| ● Complete, sign, date and return your proxy card in the envelope provided | |
| Company Performance Highlights | |
|---|---|
| White Mountains is engaged in the business of making opportunistic and value-oriented acquisitions of businesses and assets primarily in the insurance, financial services and related sectors, operating these businesses and assets through our subsidiaries and, if and when attractive exit valuations become available, selling these businesses and assets for meaningful gains. Our principal focus is to grow our book value per share metrics because we believe, based on the trading history of our stock, that over the long term our share price growth will follow our growth in these metrics. Since our IPO in 1985, including dividends, the Company has delivered annualized growth in book value per share of 13% and market value per share of 12%. The biggest driver of performance in 2025 was the sale of Bamboo. Our other operating businesses had generally solid to very good performance, and absolute investment results were good. Highlights of our 2025 operational and financial performance include: | |
| ✓ Growth in book value per share of 25% ✓ Sale of Bamboo added roughly $320 to book value per share ✓ Repurchased roughly $200 million of shares at accretive prices ✓ Acquired majority stake in Distinguished Programs ✓ Made a strategic investment in BroadStreet Partners ✓ White Mountains Partners acquired Enterprise Solutions | ✓ Effected orderly succession of CEO and CFO roles ✓ Ark/WM Outrigger produced an 81% combined ratio while growing full-year gross written premiums by 16% ✓ Bamboo generated managed premiums of $766 million, up 58% ✓ Kudu produced a 13% return on equity and deployed almost $200 million into three new managers ✓ HG Global generated premiums of $61 million, up 17% |
For more information on our business and performance highlights, please refer to page 29 of the proxy statement.
Election of Director Nominees
| Class II Nominees – Term ending in 2029 | Age | Director Since | Our Board’s Recommendation |
|---|---|---|---|
| Liam P. Caffrey | 53 | 2026 | For |
| Mary C. Choksi | 75 | 2017 | For |
| John K. Chu | 62 | Nominee for election | For |
| Weston M. Hicks | 69 | 2023 | For |
| Other Members of the Board | |||
| Reid T. Campbell | 58 | 2024 | |
| Peter M. Carlson | 61 | 2019 | |
| Suzanne F. Shank | 64 | 2021 | |
| Steven M. Yi* | 55 | 2023 | |
| Margaret Dillon | 66 | 2021 | |
| Philip A. Gelston | 73 | 2018 | |
| David A. Tanner | 67 | 2018 | |
- Not standing for reelection at completion of current term, which ends as of the 2026 Annual General Meeting
Governance Highlights
The Company’s commitment to strong corporate governance, effective risk management and strong independent oversight of management by the Board is reflected in our sound governance practices and policies. Our governance highlights (assuming the election of our current slate of nominees) include:
✓ 70% independent directors (7 out of 10) ✓ Commitment to board refreshment (four new directors since 2023) ✓ Average board tenure is 4.6 years ✓ Independent Chairman ✓ 30% gender and 20% racial/ethnic diversity ✓ Shareholder right to call a Special Meeting at 10% ✓ Annual board and committee self-evaluations ✓ Robust director and executive officer share ownership guidelines (5x cash retainer for directors and 10x salary for CEO and EVPs)
Reflects Board composition and refreshment statistics if director nominees are elected at the 2026 Annual General Meeting. 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.
For more information on our corporate governance practices, please refer to page 18 of the proxy statement.
Shareholder Outreach
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. Feedback from these discussions is shared with the Board each year. Our shareholder outreach highlights include:
For more information on our commitment to ongoing shareholder engagement and details of our 2025 shareholder outreach, please refer to page 18 of the proxy statement.
Executive Compensation Highlights
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 the Company’s shareholders. As many of our subsidiaries are engaged in the business of insurance, we evaluate the executive compensation programs of a group of insurance company peers in terms of structure and variability of payouts in good and poor performance scenarios. However, unlike most of our insurance company peers, a primary responsibility of our parent company’s management is allocating capital and opportunistically finding and executing value-creating acquisitions and dispositions of operating businesses. Over the years, transaction gains have been a large driver of success in achieving our principal objective of growing our values per share. 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 firms whose main business is derived from transactional activity such as private equity and investment banking firms, and our compensation practices must reflect this reality.
The Compensation/Nominating & Governance Committee is committed to ensuring that our executive compensation programs and governance practices motivate long-term value creation, align the financial interests of management with those of our shareholders, maintain competitiveness in the market for talent, and encourage appropriate, but not excessive, risk-taking.
| Key Compensation Highlights | |
|---|---|
| What We Do | What We Do Not Do |
| ✓ Commitment to pay for performance as evidenced by 92% of total target 2025 CEO compensation meaningfully “at risk” ✓ Half of annual LTI delivered in performance-based equity, with a three-year measurement period ✓ Formulaic annual incentive program, based on pre-determined goals ✓ Clawback policy for annual and long-term incentive plans ✓ Double-trigger change-in-control provisions ✓ Annual Say-On-Pay vote ✓ Share ownership guidelines for executive officers and directors | û No hedging of Company securities û No executive pensions û No single-trigger vesting of equity-based awards upon change-in-control û No excise tax gross-ups upon change-in-control û No dividends on unvested performance shares or restricted shares û No long-term employment agreements û No excessive perquisites or benefits |
Chief Executive Officer 1:
Other Named Executive Officers (“NEOs”):
The specifics of our compensation program begin on page 28 of the proxy statement.
Environmental, Social and Governance Practices and Disclosures
White Mountains’s Board and management are committed to sustainability and corporate responsibility as stewards of our owners’ capital. With the Board’s oversight, we have identified ESG priorities that align with both our Company’s business strategy as well as industry and investor expectations, as outlined below:
| ● | ESG in our Investment Policy: Our investment policy addresses ESG factors. We consider ESG factors when (i) making decisions in respect of internally managed portfolios and (ii) selecting external investment managers. |
| ● | Board Oversight of ESG: ESG oversight responsibilities are explicitly included in the charters of the Audit, Finance and Compensation/Nominating & Governance Committees as outlined below. |
| ● | Statement on Climate Change: We have a corporate statement on climate change, which can be found on page 24. |
| ● | ESG in Our Risk Management: We consider ESG risks, such as the impact of climate change and human capital management, in our risk management processes. Our Company website contains information on our risk management practices, including the primary frameworks used to assess risk and our approach to business continuity and the management of cybersecurity risks. |
| ● | Communication of Our ESG Practices: To respond to feedback received in our annual shareholder engagement, we developed an ESG landing page on our corporate website to communicate all of our practices more effectively, including an overview of how ESG is incorporated into our corporate governance and business ethics, our approach to climate change, our investment management activities, our human capital management, our approach to risk management and our community engagement. |
For more information on our ESG practices, please refer to page 24 of the proxy statement or the ESG landing page on our Company website (www.whitemountains.com/esg/).
WHITE MOUNTAINS INSURANCE GROUP, LTD.
The text of this filing, as the company filed it with the SEC, without its images or exhibits. This is not investment advice.