Kyle Nakatsuji

Kyle Nakatsuji is the founder and CEO of Clearcover, an AI-native auto insurance carrier, and Dearborn Labs, a forward-deployed AI practice helping P&C carriers and MGAs operationalize artificial intelligence. Over five years running production AI on real insurance operations, Kyle's team built one of the most automated carriers in the industry: 90% of claims handled by AI, 93% digital bind rate, and 3x the operational efficiency of traditional carriers. In 2026, Kyle launched Dearborn Labs to bring that operational playbook to the broader insurance market. Unlike traditional consultancies or point-solution vendors, Dearborn Labs embeds cross-functional teams that ship production AI systems in weeks, not months. Before founding Clearcover, Kyle was a venture investor at American Family Insurance, where he led insurtech investments. He speaks regularly on AI strategy in insurance and is based in Wisconsin.