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of Clearcover and Dearborn Labs to explore why the first wave of digital transformation in insurance may already be outdated.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 world
If 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.
