Liam Caffrey

Go-getter
DISC Type : d

Chief Executive Officer at White Mountains Insurance Group

Hanover, New Hampshire, United States

Overview

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.

Personality Overview

Vision Oriented

Challenger

Direct & Candid

They care equally about the product and its potential impact.  They respond well to confident salespeople. They don’t always try to control the conversation but neither do they like yielding it fully.

Topics They Care 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.
SMB Client Growth
Focused on accelerating growth and bringing new value to small and medium-sized business clients through strategic platform acquisitions.

Media Appearances

Liam Caffrey To Become CEO of White Mountains in 2026. Featured in White Mountains Insurance Group Investor Relations

See Now

Liam Caffrey Named Chief Executive Officer at White Mountains Insurance Group Ltd.. Featured in Risk & Insurance

See Now

Work History

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

Education

1996 - 1999
J.D. from Harvard Law School
1994 - 1996
M.B.A. from University of Michigan - Stephen M. Ross School of Business

More Information

Social Presence :

Prographics :

Exp : 31 Location : Hanover, New Hampshire, United States Job Level : Leadership Designation : Chief Executive Officer at White Mountains Insurance Group
URL has been copied!

Insights For Selling To Liam

During A Call Or A Meeting

DO's

  • Ask them questions confidently while doing discovery, don’t be apologetic
  • Refer to testimonials from others in similar positions
  • Highlight the competitive differentiation of your product

DONT's

  • Do not give up if they are not convinced, try again with a different approach
  • Don't try too hard to get friendly, let it happen with time
  • Don’t expect them to change their mind quickly if they say no once

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Liam is

  • Conviction in the product matters to them, followed by proof points and strong testimonials.
  • Will you ever get a clear answer from Liam

  • They may not be very forthcoming, but they will say no if needed.

Insights For Deal Planning

    How fast (or slow) will Liam move?

  • They are neither the fastest decision makers nor the slowest.
  • Can Liam take some risk or not?

  • They can take risks but after weighing up the pros and cons.

You And Liam

Personality Compatibility


More Profiles

Discover additional public profiles from our index.

Search more profiles

Looking for someone else? Search here for anyone.

Or visit Humantic AI to know more.