Executives of the Year: Monica Caldas

Liberty Mutual became the first insurer to launch a ChatGPT auto-quoting app in May, part of EVP and global CIO Monica Caldas's push to rebuild the century-old company around AI, with more than 100 AI capabilities already in production across core work such as underwriting and claims. Caldas described the effort as modernizing legacy systems while embedding AI, and framed the ChatGPT app as a bet on "agentic commerce," where buying insurance shifts from forms to conversation. "I love to solve big, hairy things with tech," Caldas said.

Monica Caldas says she likes "living on the edge." She's tasked with rewiring a century-old company for what she calls "the intelligence era." As EVP and global CIO at Liberty Mutual, her core idea is doing two hard things at once, modernizing old systems while rebuilding around AI. That means embedding AI across core work like underwriting and claims, with more than 100 capabilities already in production. In May, Liberty became the first insurer to launch a ChatGPT auto-quoting app, part of a bigger bet on "agentic commerce," where buying insurance shifts from filling out forms to simply having a conversation. “I love to solve big, hairy things with tech,” Caldas says. Her drive started early. She arrived in the U.S. from Portugal in third grade without knowing a word of English and became the first in her family to go to college.