In Episode 304 of the FNO: InsureTech Podcast, hosts Rob Beller and Lee Boyd welcome back Kyle Nakatsuji for his third appearance on the show. Kyle is the CEO and Founder of Clearcover and the founder of Dearborn Labs, a new venture focused on helping insurance organizations turn AI from strategy into execution.

Kyle explains how Dearborn Labs helps carriers, MGAs, and agencies cut through AI noise, identify high impact use cases, and implement solutions that deliver real business results. Drawing on nearly a decade of deploying production AI, he shares practical insights from claims and operations, why execution and adoption matter most, and why waiting to act is becoming increasingly risky.

Kyle also shares a brief update on Clearcover as it enters its tenth year, including improved underwriting results, a return to growth, and the launch of Clearcover Access in Florida.

Key Highlights

[03:05] Kyle Nakatsuji Returns for His Third Appearance
Why this moment feels different for AI adoption across the insurance industry.

[05:10] Clearcover at Ten Years
How a renewed focus on underwriting discipline and loss ratios set the stage for growth.

[07:40] Launching Clearcover Access in Florida
Why flexible payments and predictable fees better reflect how policyholders manage money.

[10:25] The Origin of Dearborn Labs
What Kyle saw in the market that led him to launch a firm focused on AI execution, not theory.

[13:10] Why Insurers Are Drowning in AI Noise
How vendors, pilots, and strategy decks distract from real business impact.

[16:00] Discovery Before Deployment
Why identifying the right problem to solve is the most important step in any AI initiative.

[18:55] AI Agents in Claims Operations
How Clearcover uses AI to replace recorded statements and reduce claim cycle times by up to three days.

[22:30] Adoption Matters More Than Technology
Lessons learned from rolling out AI tools inside a regulated insurance environment.

[26:00] Cross Functional Agent Based Workflows
Why claims, underwriting, and operations must work together for AI to deliver value.

[30:15] Humans, Oversight, and Judgment in an AI Driven World
What roles remain uniquely human as AI takes on more knowledge work.

[34:10] The Cost of Waiting
Why delaying meaningful AI adoption is becoming riskier for insurers.

[37:45] What Comes Next for AI in Insurance
Kyle's perspective on where agent based systems are heading and how insurers can prepare now.

Ep 304: Kyle Nakatsuji, CEO & Founder, Clearcover & Dearborn Labs

FNO: InsureTech