Monica Caldas

Leading global technology at Liberty Mutual

Monica Caldas is executive vice president and chief information officer of Liberty Mutual Insurance. She leads the company's global technology organization, which oversees information technology and data engineering across the business. A November 2024 CIO.com interview put the team she leads at about 5,000 technologists, and described her as an award-winning digital executive with a record of leading large, complex transformations.^[1][2]

Caldas described a long-term goal of having all of Liberty Mutual's 45,000 employees use its internal generative AI tool once they have been trained. That makes technology fluency a company-wide question for her, not only a question for the technology department.^[2]

Career and education

Caldas joined Liberty Mutual in 2018 as global chief information officer of its retail markets business, according to Rethinking65's coverage of her award. Rethinking65 and CIO.com both identify her as the company's chief information officer today.^[1]

She holds a bachelor's degree from the University of Connecticut and an MBA from Pennsylvania State University. Outside her day job she advocates for women in STEM and sponsors a girls-in-technology team inside the company's women in technology group, and she is active in Hispanic affinity networks.^[1]

Recognition: the 2025 CIO Leadership Award

At the 22nd annual MIT Sloan CIO Symposium on May 20, 2025, Caldas received the CIO Leadership Award, which honors chief information officers who deliver strong business value through innovative use of technology. The other finalists were Dimitris Bountolos of Ferrovial and Bill Pappas of MetLife. In her remarks she credited her team and described technology as a force multiplier for serving customers in bold new ways.^[1]

Earlier honors listed in the same coverage include her 2022 selection as a Women in Insurance Leadership honoree by Digital Insurance and a place among the Hispanic Information Technology Executive Council's 100 most influential Hispanic leaders in technology.^[1]

Technology as defense and offense

In the CIO.com interview, Caldas said technology work has a defensive side, keeping systems secure, stable and available around the clock, and an offensive side, deploying new capabilities that set the company apart. She said she aims for outcomes rather than outputs.^[2]

Her method for understanding business problems is to see the work firsthand. She described flying to Canada to sit with underwriters and learning that a tool the company had deployed was underused because it was hard to use and slow in that location. She also treats data as a shared asset: a data office outside IT handles governance and stewardship through a federated model, the technology side handles platforms and engineering, and executive data councils bring the two together.^[2]

Generative AI and Executech

On generative AI, Caldas described a Responsible AI Steering Committee that covers risk, governance, training and regulatory change, and Liberty GPT, an internal tool intended as a safe space for experimentation. About 18 months into the program, she said, roughly 25 percent of employees used Liberty GPT, more than 200 use cases had been prioritized and 10 were in production, mostly focused on productivity tasks such as summarization and question answering.^[2]

She said the program was in its third phase and that engineering teams were testing AI to automate parts of the software lifecycle. Next priorities she listed were reference architecture, choosing between large and small language models, and transforming whole processes rather than adding isolated use cases.^[2]

Her Executech program, launched several years before the interview, gives business leaders a working understanding of AI, data models, technical debt, legacy modernization and data engineering, with the aim of making technology conversations more accessible and speeding up impact.^[2]

Why she matters

Insurance is a data business run on large and often old systems, and Caldas leads technology at a company that serves customers across a wide range of markets. Her approach combines a governed enterprise AI tool, an educational program for business executives and field visits to the people who use the software, and her 2025 award from a symposium of peer CIOs recognizes that work.^[1][2]

On The Executive List

Monica Caldas is ranked No. 15 on The Executive List (October 2026) in the Chief Information Officers discipline. Her title matches the Executive List edition; the most recent sources reviewed are from 2025. The ranking reflects The Executive Review's own editorial Trending Score; it is not an outside award, and placement on the list is never sold. View the October 2026 edition.