Ep. 49 | How Agentic AI Will Rebuild Insurance Operations with Kyle Nakatsuji, Founder of ClearCover

Most insurers are asking how to add AI to existing workflows.Kyle Nakatsuji thinks that's the wrong question.In this episode of Building Tomorrow's Insurer, Nigel Fellowes-Freeman sits down with the founder of Clearcover and Dearborn Labs to explore why the first wave of digital transformation in insurance may already be outdated.After spending a decade building one of the world's best-known tech-native insurers, Kyle believes Agentic AI is forcing the industry to rethink everything from claims and underwriting to operating models and core systems.Together they discuss:• Why even modern insurers may need rebuilding for the AI era• The difference between automation and agentic systems• Why many AI initiatives stall between pilot and production• The future of headless insurance platforms• How AI changes the economics of underwriting and claims operations• Whether insurers should build proprietary AI workflows or rely on vendors• Why context, judgement and human relationships still matter• The future of embedded insurance in an AI-native worldIf you're a CEO, CIO, COO, Chief Claims Officer or transformation leader trying to understand what insurance operations could look like over the next five years, this conversation provides a practical look at what's changing now.Topics:Agentic AI in insurance, insurance digital transformation, AI claims automation, insurance operations, insurtech innovation, embedded insurance, AI underwriting, future of insurance technology, Clearcover, Dearborn Labs.