Michael Okerlund

Michael Okerlund is CEO of Cloud Court and a former IP litigator and general counsel.

He focuses on how LegalTech and AI can leverage aggregate testimony and litigation data to generate strategic insights.

Most Recent

Mining the Rich Data in P&C Claims Testimony

Property and casualty insurers that analyze testimony at scale will price risk more accurately than competitors relying on instinct alone.

Six Things

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? 

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.

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.

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.

A Strategic Shift in Insurance Distribution

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

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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