WHITE MOUNTAINS INSURANCE GROUP LTD

INFORMATION ABOUT OUR EXECUTIVE OFFICERS (as of February 27, 2026)

All executive officers of the Company are elected by the Board for a term of one year or until their successors are duly elected and qualified. Information with respect to the principal occupation and relevant business experience of the Executive Officers follows:

Mr. Caffrey was appointed as Chief Executive Officer in January 2026. Prior to that, he served as President and Chief Financial Officer of the Company since April 2024. Prior to that, he served as Executive Vice President and Chief Financial Officer. Prior to joining White Mountains in March 2022, Mr. Caffrey served as Chief Executive Officer of Aon’s Global Affinity business. Prior to that, he served as Chief Financial Officer of Aon Risk Solutions globally and as Chief Financial Officer of Aon Risk Solutions Americas. Prior to joining Aon, Mr. Caffrey spent 12 years with McKinsey & Company.

Mr. Harrison was appointed as President in January 2026. Prior to that, he served as Executive Vice President and Chief Strategy Officer of the Company. Prior to joining White Mountains in June 2024, Mr. Harrison worked for the Zurich Insurance Group from 2015 to 2024, most recently as the Chief Financial Officer of Farmers Group, Inc. Prior to joining Farmers, he was CEO of Regional Markets EMEA for Zurich Insurance Group, based in Zurich. Prior to this, he led the Zurich Group’s mergers, acquisitions and partnership activities globally. Prior to Zurich, Mr. Harrison was an investment banker at Lehman Brothers and HSBC. Mr. Harrison also serves as a director of BAM.

Mr. Papamichaelwas appointed as Managing Director and Chief Financial Officer in January 2026. Prior to that, he served as Managing Director and Deputy Chief Financial Officer. Prior to joining White Mountains in 2020, Mr. Papamichael served as a Senior Vice President at Hamilton Insurance Group. Prior to joining Hamilton, Mr. Papamichael held various senior positions at Sirius Group, including when it was owned by White Mountains prior to 2016.

Ms. Hildrethwas appointed as Managing Director and Chief Accounting Officer of the Company in May 2021. Prior to that, she served as Managing Director and General Auditor of WM Capital. She joined White Mountains in 2003 and has served in a variety of accounting and audit-related positions with the Company and its subsidiaries. Prior to joining the Company, Ms. Hildreth spent 13 years with PricewaterhouseCoopers.

Mr. Seelig is Executive Vice President and General Counsel of the Company. Since 2022, Mr. Seelig has also served as Head of Investor Relations. Prior to joining White Mountains in 2002, Mr. Seelig was with the law firm of Cravath, Swaine & Moore.