The Future of Insurance – Kyle Nakatsuji, Founder & CEO, Dearborn Labs

Episode Info

Kyle Nakatsuji is the Founder and CEO of Dearborn Labs and Clearcover. He joined the show during Season 1 to talk about Clearcover (which is the subject of one of the case studies in The Future of Insurance – Volume II. The Startups). He rejoins the show to share about their latest venture, Dearborn Labs. Here is the detail on the launch of Dearborn Labs from their press release:

Clearcover, Inc. Launches Dearborn Labs to Deploy Production AI Inside Carriers and MGAs 

Backed by nearly a decade of proven results, the firm’s AI concierge model designs, builds and deploys customized AI infrastructure into insurers’ existing operations to eliminate fragmented pilots 

CHICAGO, March 5, 2026 — Clearcover, an AI-native auto insurance carrier, today announces the launch of Dearborn Labs, a forward-deployed AI practice that builds and operates AI systems inside property and casualty insurance carriers and MGAs. 

"Most carriers have already invested in AI. The problem isn't the tools," said Dearborn Labs Founder Kyle Nakatsuji. "It's that the landscape changes faster than any single solution can keep up with, and nobody's connecting the data and context across operations to make those tools compound. That's not a software problem. It's an operating problem." 

Unlike traditional SaaS, Dearborn Labs adds an operational layer to customize AI within a company’s unique model, driving measurable business outcomes. 

"We don't hand over a strategy deck. We deploy into your operation and ship production systems in weeks," said Nakatsuji, adding that modern insurers need to turn isolated AI capabilities into a growth engine. "Your claims data should make your underwriting smarter. Your underwriting context should shape your distribution. We build the infrastructure that makes that happen." 

While the insurance industry has invested heavily in AI, most carriers and MGAs have not yet seen system-level returns. 

Nakatsuji's team at Clearcover integrated AI into nearly every core function of daily production across multiple states and significantly improved results: Over 90% of claims intake runs through AI agents, 93% of policies are bound digitally and claims handling operates at three times the efficiency of traditional carriers.

Episode Overview:

• Clearcover's Tech Foundation: Built on a decade of tech innovation for better customer experiences and efficiency in insurance.
• Dearborn Labs' Mission: A new venture focused on helping insurers adopt AI, offering a hybrid service and technology approach.
• Urgency of AI Adoption: The current AI advancements necessitate immediate action; waiting means falling behind.
• Beyond Off-the-Shelf Solutions: Dearborn Labs focuses on tailored AI strategies and team deployment, not just software sales.
• The Critical Data Layer: Effective AI requires a unified data foundation to provide context across all business functions.
• Incremental Steps, Exponential Gains: While the industry is incremental, AI allows for rapid progress and significant results.
• AI as "Employees": AI agents can act as specialized "staff," drastically changing operational efficiency and economics.
• Future Uncertainty, Present Action: The pace of AI change is unprecedented, making immediate engagement crucial for future relevance.

This episode is brought to you by The Future of Insurance book series (future-of-insurance.com) from Bryan Falchuk.

Follow the podcast at future-of-insurance.com/podcast for more details and other episodes.

Music courtesy of Hyperbeat Music, available to stream or download on Spotify, Apple Music, and Amazon Music and more.