Kyle Nakatsuji

Kyle Nakatsuji is the founder and CEO of Clearcover, an AI-native auto insurance carrier, and Dearborn Labs, which helps P&C carriers and MGAs operationalize artificial intelligence.

Before founding Clearcover, he was a venture investor at American Family Insurance, where he led insurtech investments. He speaks regularly on AI strategy in insurance.

Most Recent

MGAs Don't Have an AI Problem.

MGAs Don't Have an AI Problem

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MGAs have grown to $114 billion in premium but lack time and capital to build AI infrastructure themselves.

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Traditional Insurers Can Still Win AI Race

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Incumbents have operational context advantages AI-native startups can't replicate, but the window to leverage them is closing.

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So Your Start-Up Will Sell Insurance?

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There are four distribution models to consider: lead generation, agency/brokerage, managing general agency and carrier.

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New Products and Combined Approaches

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New insurance experiences can combine “Insurance 2.0” distribution and structural and product innovation and have a dramatic impact.

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Is P2P a Realistic Alternative?

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By redefining the traditional structure, P2P can offer unique benefits. So can private-investor-backed insurance. But with caveats....

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Insurance 2.0: How Distribution Evolves

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In designing business models and products for Insurance 2.0, customers should be thought of as <em>intent-driven</em> or <em>opportunity-driven.</em>

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Insurance AI

The Underlying Question for Insurance AI

By Paul Carroll

The question is: When is good enough good enough? The answer depends on whether you see AI as a math/science problem or as a legal/regulatory one.

It Wasn't a Decision. It Was a Default.

There is a question about AI no one is asking out loud: Are the efficiencies worth more as a cost saving, or as time freed up for other work? 

1

The AI-Informed Homeowner Is Already Here

Homeowners are using AI to research coverage and compare policies before meeting agents, fundamentally reshaping the insurance buying process.

2

What Cyber Underwriting Is Missing

Cyber underwriting has become adept at measuring technology. The missing signal may be the condition of the organization responsible for keeping it secure.

3

Resting Heart Rate Reshapes Underwriting

Resting heart rate emerges as a powerful, underused mortality predictor that may outperform traditional underwriting metrics like cholesterol and BMI.

4

A Strategic Shift in Insurance Distribution

Insurance carriers are shifting from merely managing producer networks to leveraging distribution data for strategic competitive advantage.

5

Smart Glasses Transform Insurance Claims, Inspections

Smart glasses are standardizing insurance inspections through real-time documentation and AI-guided workflows that improve transparency and reduce claim processing delays.

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Becoming a Frontier Insurer

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AI Won’t Fix the Agency. Re-architecting It Will

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Mining the Rich Data in P&C Claims Testimony

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Michael Okerlund

Testimony as the Currency of P&C Claims

MGAs Don't Have an AI Problem

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MGAs Don't Have an AI Problem.

A Breakthrough for AI Agents on Claims

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5 Lessons Learned From NYC Flooding

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Jonathan Jackson

Five Lessons Learned from NYC Flooding

Making AI Work in Commercial Submission Intake

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Making AI Work in Commercial Submission Intake

R&W Insurance Deserves a Closer Look

By

Joseph Cosentino

R&W Insurance Gains