Liberty Mutual CIO Named 2026 Executive of the Year
Monica Caldas has led the insurance firm's integration of over 100 artificial intelligence capabilities into its core business workflows.
Updated on Sept. 22, 2026 in Artificial Intelligence
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TIME has recognized Liberty Mutual EVP and global CIO Monica Caldas as a 2026 Executive of the Year. This follows her leadership in embedding more than 100 AI capabilities into the company's production environment.
Why it matters
The recognition reflects an industry-wide pivot toward replacing static legacy insurance systems with dynamic, conversational interfaces. Liberty Mutual is currently leveraging this strategy to rebuild its underwriting and claims infrastructure around AI-first processes.
Liberty Mutual now has over 100 AI capabilities deployed in production. This infrastructure enables a transition from traditional document-based insurance forms to conversational, automated quoting systems.
The players
Monica Caldas
The Executive Vice President and global Chief Information Officer at Liberty Mutual who is overseeing the firm's AI-driven legacy system transformation.
Liberty Mutual
A major U.S.-based insurance provider currently shifting its technological stack from traditional legacy software to AI-integrated underwriting and claims processing.
The details
Under the direction of Caldas, the firm has integrated AI directly into underwriting and claims workflows. This process replaces manual data entry with conversational models, such as the ChatGPT-powered auto-quoting application launched in May 2026. These tools function by automating the intake of customer information, allowing the underlying risk-assessment algorithms to process applications without human-to-form data migration.
Timeline
May 2026: Liberty Mutual launched a ChatGPT auto-quoting app.
2026: Monica Caldas was named Executive of the Year.
The Tech Race
This effort represents an aggressive modernization of insurance software, moving the industry away from legacy systems that have historically limited automation. It signals a shift where insurers are competing on the speed and conversational fluidity of their underwriting engines rather than traditional manual processing.
Customers interacting with Liberty Mutual are seeing a transition from static digital forms to conversational quoting processes. This shift changes the user experience from manual document submission to interactive chat, though specific rollout timelines for further applications remain unannounced.
The takeaway
The transformation of insurance from form-based entry to conversational interaction is now a benchmark for institutional digital modernization. Observers should track the company's progress in expanding these 100 production AI capabilities to determine if this results in faster, more accurate claim resolution times.
Further reading
For more on the current state of large-scale model deployment in business, explore Artificial Intelligence.
Source note: This article includes information reported by TIME.
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