Insurance
10 Liberty Mutual IT leaders
These ten people hold or have held CIO, CTO and technology vice president roles at Liberty Mutual Insurance, including Liberty Mutual's global CIO and CIOs for its Europe and Latin America, Asia and Global Risk Solutions businesses. A reader can learn how IT leaders lead technology organizations in insurance businesses.
Professionals to explore
01—10David Freedman
LinkedInExperience: Chief Information Officer, Europe and Latin America · Liberty Mutual Insurance
Chief Information Officer, Europe and Latin America at Liberty Mutual Insurance since January 2020; the profile describes the role as CIO for Liberty Mutual Global Retail Markets' West region, leading a distributed team of 600 across eight countries. David Freedman was Digital Chief Technology Officer and Senior Vice President at Wells Fargo (2017–2020).
David Tam
LinkedInExperience: Regional APAC CIO, Liberty International Insurance · Liberty Mutual Insurance
Regional APAC CIO, Liberty International Insurance at Liberty Mutual Insurance since November 2024, and former Asia Regional CIO - Retail Markets there (2017–2024), a role the profile says led technology strategy and teams in countries including China, India, Hong Kong, Malaysia and Singapore. David Tam was Chief Information Officer at Liberty Insurance Singapore (2013–2017) and Liberty Insurance Vietnam (2011–2013).
Johnathan Reardon
LinkedInExperience: CIO, North America & Global Surety, Global Risk Solutions · Liberty Mutual Insurance
CIO, North America & Global Surety, Global Risk Solutions at Liberty Mutual Insurance since March 2026, a C-Level role in Engineering and Technical according to the profile, and VP & Sr. Director, Global Risk Solutions Technology there since July 2018. Johnathan Reardon was VP & Sr. Director, Global Retail Markets Technology at Liberty Mutual Insurance (2008–2018).
Mark Cressey
LinkedInExperience: Senior Vice President and CIO of the Commercial Markets Strategic Business Unit · Liberty Mutual Insurance
Former Senior Vice President and CIO of the Commercial Markets Strategic Business Unit (2006–2010) and former CIO, Corporate Center Application Portfolio (2001–2006) at Liberty Mutual Insurance. Mark Cressey's current row is EVP and General Manager, Tech Global Digital Services at Liberty Mutual Insurance, and the profile cites experience leading global IT infrastructure systems and mobile technology.
Michael Willock
LinkedInExperience: CTO Investments, CIO Corporate Functions · Liberty Mutual Insurance
Former CTO Investments, CIO Corporate Functions at Liberty Mutual Insurance (2022–2026), and Chief Technology Officer, Investments, Data, Experience there since April 2026, a role in which the profile says Michael Willock leads technology for Liberty Mutual Investments and manages enterprise data, data science and AI capabilities Liberty-wide. Former SVP Asset Management Technology at Fidelity Investments (2002–2018).
Monica Caldas
LinkedInExperience: Global Chief Information Officer · Liberty Mutual Insurance
Global Chief Information Officer at Liberty Mutual Insurance since January 2023. Monica Caldas was also EVP, Global Deputy Chief Information Officer (2022–2023) and EVP & Chief Information Officer, Global Retail Markets (2018–2023) at Liberty Mutual Insurance, and Global Chief Information Officer at GE Transportation, a Wabtec company (2017–2018).
Paul McCarthy
LinkedInExperience: Chief Information Officer, Global Risk Solutions International (interim) · Liberty Mutual Insurance
Chief Information Officer, Global Risk Solutions International (interim) at Liberty Mutual Insurance since February 2023. Paul McCarthy was Snr Director, Technology, Global Applications at Liberty Mutual Insurance (2020–2023), Applications Director - Liberty Mutual Western Europe Markets (2018–2020) and Chief Information Officer at Liberty Insurance Ireland (2017–2018).
Rick Belsky
LinkedInExperience: Vice President and Senior Director, Technology · Liberty Mutual Insurance
Vice President and Senior Director, Technology at Liberty Mutual Insurance since January 2018; the profile describes Rick Belsky as head of global voice and data communications on the IT Senior Leadership Team, reporting to the GM and SVP Hosting Services. Rick Belsky was Vice President of Engineering (2007–2018) and Director of Infrastructure (2004–2007) at Agero, Inc.
Stephen Winter
LinkedInExperience: VP & Senior Director, Technology · Liberty Mutual Insurance
VP & Senior Director, Technology at Liberty Mutual Insurance since October 2012, based in Boston; the profile says the role is responsible for providing secure, high-performing, and cost competitive technology environments. At Liberty Mutual Insurance Stephen Winter was also Information Security Officer (2007–2012) and Systems Manager (2003–2007).
Wenda He
LinkedInExperience: Chief Information Officer, Asia Market · Liberty Mutual Insurance
Chief Information Officer, Asia Market at Liberty Mutual Insurance since January 2020; the profile says Wenda He leads a team of IT professionals across four countries and oversees IT strategy through execution for a half billion USD revenue operation. Former Chief of Staff & Head of Strategy, East Region at Liberty Mutual Insurance (2012–2019).
Choose the right perspective
Match the person's scope to your question, since a global or regional CIO sees different trade-offs than a vice president who runs one technology domain such as communications or infrastructure. Check each person's dates so you know whether their Liberty Mutual experience is current or from an earlier period.
Questions to take into the conversation
- 01How does a global insurer decide which technology decisions sit with the global CIO and which sit with regional CIOs?
- 02What does it take to run IT for insurance operations across several countries with different regulators?
- 03How do you modernize core insurance platforms while keeping costs and service levels under control?
Reaching Liberty Mutual IT leaders
How can I contact one of these Liberty Mutual IT leaders?
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How much does it cost to reach Liberty Mutual IT leaders?
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About this directory
This is a professional research starting point based on business profile data retrieved on . Titles and companies reflect that source snapshot and may describe past or present roles. Check the linked profiles for current details. Inclusion does not imply Instant Expert membership or availability.
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