White Mountains Insurance (WTM) provides the following major products and services:

• Municipal Bond Insurance: Provides insurance on municipal bonds issued to finance public purposes.
• Reinsurance: Offers reinsurance across various lines, including property, marine, energy, accident and health, and casualty.
• Direct Insurance: Writes a portfolio of direct insurance, including property, marine and energy, accident and health, casualty, and specialty products.
• Specialty Property and Casualty Insurance Programs: Operates as a managing general agent and program administrator for specialty property and casualty insurance in specific sectors.
• Capital Solutions for Asset and Wealth Managers: Provides capital for ownership transfers, management buyouts, acquisitions, growth finances, and legacy partner liquidity to boutique asset and wealth managers.
• Travel Insurance: Offers insurance solutions to the travel industry through brokers and direct-to-consumer channels.
• Investment Management (Insurance-Linked Securities): Manages investments in insurance-linked securities like catastrophe bonds and collateralized reinsurance for third-party clients.

White Mountains Insurance Group, Ltd. (WTM) primarily serves other companies and institutions across its various segments, but also provides services directly to individuals in specific niches. No specific customer company names are provided in the background description; however, the major categories of customers can be identified as follows:

Major Customer Categories (Companies and Institutions)

• Municipalities: Customers of the HG Global/BAM segment, requiring insurance on municipal bonds issued to finance public purposes, such as schools, utilities, and transportation facilities.
• Other Insurance Companies: Benefiting from reinsurance protection services offered by the HG Global/BAM and Ark segments, and as third-party clients for insurance-linked securities management within the Other Operations segment.
• Boutique Asset and Wealth Managers: Clients of the Kudu segment, seeking capital solutions for generational ownership transfers, management buyouts, acquisitions, growth finances, and legacy partner liquidity, as well as strategic assistance.
• Businesses in Specialized Sectors: Including those in specialty transportation, real estate, and social services, which are served by the NSM segment through its managing general agent and program administrator services for specialty property and casualty insurance.
• Travel Industry Businesses: Including entities within the travel industry that receive insurance solutions through broker channels from the Other Operations segment.

Major Customer Categories (Individuals)

• Pet Owners: Individuals purchasing pet insurance facilitated through the NSM segment.
• Travelers: Individuals acquiring travel insurance directly from the Other Operations segment.

Liam Caffrey, Chief Executive Officer

Liam Caffrey was appointed Chief Executive Officer of White Mountains Insurance Group, Ltd. effective January 1, 2026. Prior to this role, Mr. Caffrey served as President & Chief Financial Officer of the company. He joined White Mountains in 2022, initially as Executive Vice President & Chief Financial Officer. Before joining White Mountains, Mr. Caffrey was the CEO of Aon's Global Affinity business. He began his tenure at Aon in 2012 as Chief Financial Officer of Aon Risk Solutions Americas and later became CFO of Aon Risk Solutions globally. Earlier in his career, Mr. Caffrey served as a principal at McKinsey & Company and worked as an engineer for General Motors.

Michael Papamichael, Chief Financial Officer

Michael Papamichael will succeed Liam Caffrey as Chief Financial Officer of White Mountains Insurance Group, Ltd. on January 1, 2026. He rejoined White Mountains in 2020 after serving as Senior Vice President at Hamilton Insurance Group from 2018. Before his time at Hamilton, Mr. Papamichael held several senior roles at Sirius Group, including when it was under White Mountains' ownership prior to 2016.

Giles Harrison, President

Giles Harrison will assume the role of President of White Mountains Insurance Group, Ltd. on January 1, 2026. He joined the company in June 2024, having previously served as Chief Financial Officer of Farmers Group, Inc. during his tenure at Zurich Insurance Group.

Jonathan Cramer, Chief Investment Officer

Jonathan Cramer serves as the Chief Investment Officer of White Mountains Insurance Group, Ltd.

Rob Seelig, General Counsel / Investor Relations

Rob Seelig holds the position of General Counsel and is responsible for Investor Relations at White Mountains Insurance Group, Ltd.

The key risks to White Mountains Insurance (symbol: WTM) include investment volatility, dependence on key personnel, and exposure to catastrophic events.

1. Investment Volatility and Market-Sensitive Valuations: White Mountains Insurance Group's financial performance is significantly exposed to the volatility of its investment portfolio and market-sensitive valuations. The company's diverse operations, particularly through its Kudu segment which provides capital solutions to asset and wealth managers, and its stakes in various entities like MediaAlpha, increase its exposure to market fluctuations and impact cash flow streams. Material exposures include interest-rate sensitivity across its substantial cash and fixed-income portfolio.
2. Dependence on Key Personnel: The success of White Mountains Insurance Group is heavily reliant on the expertise and performance of its key personnel. The potential loss of such individuals could disrupt operations and negatively affect the company's performance. The competitive nature of the talent market in the insurance industry also poses ongoing challenges in attracting and retaining skilled professionals. Additionally, an upcoming leadership transition, including changes in the CEO and CFO roles in early 2026, introduces a layer of strategic uncertainty for investors.
3. Catastrophe Exposure: As an insurance and reinsurance provider, particularly through its Ark segment which writes property, marine and energy, and other reinsurance products, White Mountains Insurance Group faces inherent exposure to catastrophic events. Claims arising from events such as hurricanes, earthquakes, floods, fires, and other severe weather or man-made disasters can lead to significant losses and impact profitability. The company experiences material exposure from catastrophe-driven loss volatility.

The clear emerging threats for White Mountains Insurance (WTM) are:

• Technological disruption and disintermediation in insurance distribution: The NSM segment operates as a managing general agent and program administrator. The rise of advanced Insurtech platforms leveraging AI and data analytics could enable insurance carriers to manage specialty programs more directly or give rise to new, digitally native MGAs and program administrators with significantly more efficient operations and lower cost structures, thereby threatening NSM's traditional role and market share.
• The growth of embedded insurance and direct distribution models: The "Other Operations" segment offers travel insurance through a broker channel and on a direct-to-consumer basis. The increasing trend of "embedded insurance," where travel providers (e.g., airlines, online travel agencies) integrate insurance offerings directly into their booking processes as a seamless add-on, could diminish the need for separate broker channels or standalone direct-to-consumer providers, similar to how platform businesses have bypassed traditional intermediaries.

White Mountains Insurance Group, Ltd. (WTM) operates across several key segments, each addressing significant addressable markets:

• Municipal Bond Insurance (HG Global/BAM segment): The total municipal bond issuance in the U.S. reached $580 billion in 2025. The insured share of total municipal issuance in the U.S. was approximately 7.9% from January through June of 2025. The top two municipal bond insurers collectively wrapped over $42.828 billion in 2025 in the U.S. U.S. insurers' total investment in municipal bonds was $434.3 billion at year-end 2024, with total municipal bonds outstanding at $4.2 trillion.

• Reinsurance (Ark segment): The global reinsurance market was valued at approximately USD 621.39 billion in 2025 and is projected to grow to USD 1403.7 billion by 2034. Other estimates for the global market include USD 711.75 billion in 2024, reaching USD 2000.08 billion by 2034, and USD 472.3 billion in 2025, reaching USD 1 Trillion in 2035. North America represented more than 44% of the global reinsurance market revenue in 2024, with the U.S. contributing approximately USD 137.7 billion in 2025. Europe held a 37% market share in 2025.

• Specialty Property and Casualty Insurance (Ark and NSM segments): The global specialty insurance market was valued at USD 130.54 billion in 2025 and is projected to reach USD 285.99 billion by 2033. The U.S. property and casualty insurance market was valued at USD 1.10 trillion in 2025 and is projected to reach USD 1.33 trillion by 2030. North America's property and casualty insurance market was valued at USD 853.13 billion in 2025, with the U.S. market specifically expected to hold USD 733.03 billion in 2025. Specialty lines within the U.S. property and casualty insurance market are projected to grow at a 5.54% CAGR through 2031.

• Capital Solutions to Boutique Asset and Wealth Managers (Kudu segment): The global asset and wealth management industry's assets under management (AUM) reached a record $135 trillion in 2024. Consolidation in the asset and wealth management industry is expected to result in over 1,500 significant mergers and acquisitions by 2029 among firms managing at least $1 billion in assets. In the U.S., there were 182 announced wealth advisory M&A transactions as of June 30, 2025, with deal volume almost doubling from 185 transactions in 2020 to 353 in 2024. Insurance brokerages acquired 27 wealth management and retirement firms in 2025 as of November.

• Travel Insurance (Other Operations segment): The global travel insurance market was valued at approximately USD 27.14 billion in 2025 and is predicted to grow to about USD 98.74 billion by 2034. Other projections for the global market include USD 31.25 billion in 2025, growing to USD 140.78 billion by 2034, and USD 25.98 billion in 2025, reaching USD 62.53 billion by 2031. Europe consistently held the largest share of the travel insurance market, with estimates ranging from 36.0% to 51.70% in 2025.

• Insurance-Linked Securities (ILS), including Catastrophe Bonds (Other Operations segment): The insurance-linked securities (ILS) market reached a record $107 billion in capacity globally at the end of 2024. The 144A natural catastrophe bond market alone surpassed $45 billion by the end of 2024. Collateralized reinsurance capacity was estimated between $45 billion and $50 billion at the end of 2024, and industry loss warranty capacity remained flat at $5 billion to $7 billion. The total catastrophe bond market (new and outstanding issues) climbed to $55.8 billion in the first six months of 2025, and the outstanding catastrophe bond market ended 2025 at just over $61.3 billion. The overall ILS market size surpassed US$56 billion in the first half of 2025.

Here are 3-5 expected drivers of future revenue growth for White Mountains Insurance (WTM) over the next 2-3 years:

1. Continued Growth in the Ark Segment: The Ark segment, which specializes in property and casualty insurance and reinsurance, is expected to continue its growth trajectory. In 2025, Ark produced $2.6 billion in gross written premiums, representing a 16% increase, showcasing successful underwriting expansion and rate increases in specialty lines. This momentum, including a 27% increase in gross written premiums in Q1 2025, indicates sustained expansion within its core insurance offerings.
2. Strategic Investments and Expansion within the Kudu Segment: The Kudu segment, which provides capital solutions to asset and wealth managers, is a significant driver of revenue growth. Kudu demonstrated strong performance in 2025 with a 13% return on equity and an 8% growth in the fair value of its portfolio of participation contracts on a same-store basis. Its ability to grow the fair value of its participation contracts and EBITDA, as observed in Q3 2025, suggests continued expansion in this area.
3. Deployment of Undeployed Capital for Acquisitions and Investments: White Mountains Insurance significantly increased its undeployed capital to approximately $1.1 billion following the sale of a control stake in Bamboo. This substantial "dry powder" is anticipated to be strategically deployed by the new leadership team in early 2026 for future acquisitions and investments across its segments, which should directly contribute to revenue expansion.
4. Growth Through Acquisitions within the Other Operations Segment: The "Other Operations" segment has already demonstrated significant revenue increases due to recent strategic acquisitions. For instance, the acquisition of Enterprise Solutions by WTM Partners in Q2 2025 substantially boosted this segment's revenue, pushing it to $70 million in the first half of 2025, a considerable increase from the prior year. The consolidation of Enterprise Solutions also drove increases in other revenues in Q4 2025 and for the full year 2025. Additionally, the acquisition of Distinguished Programs in Q3 2025 further diversified this segment, indicating a continued focus on growth through strategic additions.

Share Repurchases

• White Mountains repurchased and retired 100,581 of its common shares for $203 million in the year ended December 31, 2025.
• The company commenced a "modified Dutch auction" self-tender offer on November 21, 2025, to purchase up to $300 million in value of its common shares.
• In 2022, White Mountains allocated $0.6 billion towards share repurchases.

Share Issuance

• White Mountains president Giles E. Harrison received 775 restricted common shares on February 25, 2026, as equity compensation.

Outbound Investments

• In 2025, White Mountains acquired a controlling financial interest in Distinguished for $225 million.
• WTM Partners, launched in October 2023, deployed $58 million in Enterprise Solutions in 2025.
• White Mountains committed $150 million of capital to WM Outrigger Re for the 2025 underwriting year.