Born AI-Native
Clearcover wasn't an insurance company that adopted AI. It was an AI company that learned insurance — from the inside, for a decade.
In 2016, we started Clearcover at 415 North Dearborn Street in Chicago with a question most people in insurance weren't asking: what happens when you build an insurer from scratch on AI?
Not AI bolted onto legacy systems. Not a chatbot stapled to a 40-year-old policy admin platform. A ground-up operating system where every workflow — quoting, underwriting, claims, customer service — was designed around technology from day one.
We spent the next decade finding out what works and what doesn't. We built models that quote in under a minute. Automated claims processes that used to take weeks. Agentic servicing tools that now handle 50%+ of inbound chats.
"A ground-up operating system where every workflow was designed around technology from day one."
We also learned the hard parts. The places where AI breaks in insurance aren't where most people think. It's not the algorithms. It's the context — the fragmented data, the institutional knowledge trapped in people's heads, the regulatory nuance that no foundation model understands out of the box.
That's what a decade of operating teaches you. Not theory. Operating knowledge.
Dearborn Labs is how we bring that operating system to the rest of the industry.
Every carrier is facing the same question we asked in 2016. Most are trying to answer it with partners who've never run a book of business, never filed a rate, never explained an AI decision to a regulator.
We have. For ten years. And now we're building the tools, frameworks, and implementation partnerships to help carriers who want to move — but need a guide who's already made the trip.
Operators. Builders. Forward Deployed.
AI Navigators
We help companies cut through the noise. AI capabilities shift daily. We help non-technologist operators identify what's real, what's relevant to their business, and what's actually worth pursuing.
Forward-Deployed Operators
We embed with teams until transformation is complete. We understand their systems, constraints, and culture because we become part of their organization during transformation.
Long-term Transformation Partners
We ship working systems, not recommendations. We don't leave when the project is "done." We partner, we build, we maintain, we train. Our success is measured by our clients' operational improvements, not billable hours.
A Differentiated Approach
Strategy and execution by insurance operators with a decade of production AI. We didn't study the problem. We lived it.
// Name origin
The name comes from where we started. 415 North Dearborn. The lab where we built the thing before we knew what to call it.
Ready to build with us?
Start with a discovery sprint. We'll show you what's possible.