Liberty Mutual, Travelers Discuss When Not to Modernize Systems
In a panel discussion at the 2026 MIT Sloan CIO Symposium, Liberty Mutual Insurance Global CIO Monica Caldas and Travelers Insurance Chief Technology and Operations Officer Mojgan Lefebvre explored the trade-offs of enterprise system modernization. Both executives noted that in the new AI-driven era, not all legacy systems require immediate upgrades, and knowing what not to do is equally important. Caldas introduced Liberty Mutual's technical debt radar framework to distinguish systems that need immediate attention, monitoring, or stability maintenance; Lefebvre shared Travelers' strategy of isolating subsystems behind APIs and investing around customer value. Thanks to a cloud migration started eight years ago, Travelers has placed 70% of its computing workloads in the cloud, laying a solid foundation for AI applications.
Cambridge, Massachusetts — If chief information officers need a use case to convince their enterprises that system modernization is a critical investment, artificial intelligence provides the best evidence. Today, legacy infrastructure can hold back enterprise AI ambitions that demand high levels of data and computing power.
However, for technology executives, developing a modernization roadmap can be challenging. They must balance which processes need immediate upgrades within budget, while ensuring legacy systems remain stable. Sometimes, the best course of action is determining which parts should not be modernized.
To simplify this decision-making process, Liberty Mutual Insurance focuses on key metrics and the potential business outcomes of modernization efforts, said the company's executive vice president and global CIO Monica Caldas during a panel discussion at the 2026 MIT Sloan CIO Symposium .
"We use the technical debt radar as an example to understand which items need immediate attention, which need monitoring, and which can remain stable," Caldas said. The framework includes multiple variables that help the company determine where to focus from a business and product perspective.
Travelers Insurance has taken a similar approach, focusing its modernization efforts on systems that enhance customer experience or improve operational efficiency.
"You should modernize systems that are on the critical path," said Travelers' executive vice president and chief technology and operations officer Mojgan Lefebvre during the same panel discussion. "We choose not to modernize certain systems, but instead isolate them behind APIs and invest in areas that drive customer value or productivity gains."
AI adoption plans are influencing the mix of modernization decisions. Lefebvre said Travelers is working to identify priority areas, starting with the parts where AI deployment is critical. She noted that modernization is key for enterprises struggling with data accessibility and AI adoption plans.
"Ultimately, the goal is to complete as much modernization as possible, in the right order," Lefebvre said.
AI-focused upgrades
Insurance industry players such as Travelers and Liberty Mutual have actively driven AI adoption, focusing on applications that can help reduce operational costs and improve customer service. Similar to their banking peers, modernizing legacy systems has become a prerequisite for handling related use cases.
According to Lefebvre, Travelers is reaping the benefits of early cloud modernization efforts that have laid a solid foundation for AI.
"We are fortunate that Travelers began platform modernization efforts very aggressively eight years ago," Lefebvre said. "Currently, 70% of our compute workloads are in the cloud."
Lefebvre said this foundation has enabled the insurer to advance AI adoption plans, including opportunities to rethink parts of the claims process.
"We are thinking about how to handle customer calls in a completely different way," Lefebvre said. The company has applied automation technology to the process where personal auto insurance customers submit their first notice of loss after physical damage. This change allows most customers to complete the process with the support of an AI agent.
Caldas said modernization decisions also require clear alignment at the executive level.
"You have to align at the top of the company because you are making decisions about investments," Caldas said. "But it doesn't stop there—that consensus must truly cascade down."
Correction: This article has been updated to more accurately reflect the specific aspects of the loss notice process automation.