# Monica Caldas transforms insurance for the AI era

> Liberty Mutual's CIO is modernizing a century-old company by embedding AI across core operations while rebuilding legacy systems.
- Title: Monica Caldas transforms insurance for the AI era · TIME
- Summary: Liberty Mutual's CIO is modernizing a century-old company by embedding AI across core operations while rebuilding legacy systems. Successful digital…
- Keywords: monica caldas, liberty mutual, chief information officer, ai transformation, insurance technology, legacy system modernization, chatgpt, agentic commerce, underwriting, claims processing, Monica, Caldas
- Source: TIME — https://time.com/collection/executives-of-the-year-tech-data/2026/monica-caldas
- Published: 2026-09-22T13:01:03.961+00:00
- Read time: 1 min
- Topics: monica caldas, liberty mutual, chief information officer, ai transformation, insurance technology, legacy system modernization, chatgpt, agentic commerce, underwriting, claims processing
## Rewiring insurance for AI
Monica Caldas, EVP and global CIO at Liberty Mutual, is modernizing a century-old company for what she calls the intelligence era. Her strategy tackles two challenges at once: updating legacy systems while rebuilding around AI capabilities.
## AI embedded across core work
Liberty Mutual has deployed more than 100 AI capabilities in production, embedding artificial intelligence across core insurance work like underwriting and claims processing. This represents a major shift in how the company operates.
## ChatGPT auto-quoting app launches
In May, Liberty Mutual became the first insurer to launch a ChatGPT-powered auto-quoting app. The move signals a shift toward agentic commerce, where customers buy insurance through conversation rather than filling out forms.
## Caldas loves solving big problems
Caldas describes herself as someone who likes living on the edge and loves solving big, hairy problems with technology. Her drive to tackle complex challenges shapes her approach to transforming Liberty Mutual.

> I love to solve big, hairy things with tech
## From Portugal to tech leadership
Caldas arrived in the U.S. from Portugal in third grade without knowing English and became the first in her family to attend college. Her early experience overcoming barriers shaped her approach to tackling difficult technical challenges.
## Key takeaway

Successful digital transformation requires doing two hard things simultaneously: maintaining existing systems while building new AI-powered capabilities.