Liam Caffrey in

Liam Caffrey

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Chief Executive Officer at White Mountains Insurance Group
📍 Hanover, New Hampshire, United States

Liam Caffrey is the CEO of White Mountains Insurance Group. With a JD from Harvard Law School and an MBA from the University of Michigan, his career includes senior finance and operating roles at Aon and as a principal at McKinsey & Company. He has extensive experience in insurance-related M&A and operations.

A public tax filing from February 2026 lists Liam Caffrey as a board member for the Adler Planetarium in Chicago, indicating an interest in astronomy and community involvement in the arts and sciences.

He co-founded Second City Advisors, an independent consultancy serving companies and financial sponsors in the insurance sector.

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Experience
31 Years
Current Role
Chief Executive Officer
Job Level
Leadership
Location
Hanover, New Hampshire, United States
Personality Overview

How Liam shows up

Communication Style
Decision Approach
Work Preference

Behavioral traits and communication patterns that shape how this person evaluates opportunities, builds trust, and makes decisions in professional settings.

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Priorities

Topics Liam cares about

Digital Insurance
Expressed excitement about delivering digital insurance to small and medium-sized clients through acquisitions like CoverWallet.
Insurance M&A
His career reflects deep experience in insurance-related M&A, from roles at Aon and McKinsey to co-founding an insurance-focused consultancy.
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Career

Work history

1-2026
Chief Executive Officer
White Mountains Insurance Group
4-2024 - 1-2026
President & Chief Financial Officer
White Mountains Insurance Group
3-2022 - 4-2024
EVP & Chief Financial Officer
White Mountains Insurance Group
4-2021 - 3-2022
Co-Founder and Principal
Second City Advisors
4-2021 - 11-2021
Executive In Residence
Warburg Pincus LLC
In the press

Media appearances

Liam Caffrey To Become CEO of White Mountains in 2026. Featured in White Mountains Insurance Group Investor Relations
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Liam Caffrey Named Chief Executive Officer at White Mountains Insurance Group Ltd.. Featured in Risk & Insurance
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Education
1996 - 1999
J.D.
Harvard Law School
1994 - 1996
M.B.A.
University of Michigan - Stephen M. Ross School of Business
Social presence
in
Behavioral profile

DISC profile (public)

DISC behavioral profile

Dominance, influence, steadiness, and calculativeness scores with guidance on how this person prefers to communicate and decide.

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