Head of Property Underwriting

Job Description

Corgi | Chicago (in office) | Property Underwriting

$175,000 - $300,000 base + equity

About Corgi

Corgi is an AI-first property and casualty insurance carrier backed by Y Combinator (S24). We're building a surplus lines carrier from the ground up: our own paper, our own forms, our own rating, and software that gets a policy bound in hours instead of weeks.

We're building our property book on our own paper, from commercial property to builders risk. We need someone who owns how we underwrite it and how much of it we let pile up in one place.

About the Role

As Head of Property Underwriting, you'll own how Corgi underwrites property risk: appetite, guidelines, valuation, catastrophe exposure, and results. You'll decide what we write, where, and at what aggregate, and you'll be accountable for how the property book performs. You'll work side by side with our SWEs and product team to turn that judgment into rating logic, data checks, and referral rules the system enforces on every quote.

This is a builder role on a small, fast-moving team. You won't inherit a mature department. You'll design one.

What You'll Do

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• Set property appetite by occupancy, construction, protection, and geography, and write and maintain the underwriting guidelines, authority levels, and referral rules that govern it.
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• Own valuation discipline: insurance-to-value, statement of values review, coinsurance, and deductible structure, including wind, hail, earthquake, and wildfire.
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• Work with SWEs and actuarial resources to build and refine property rating logic, and wire catastrophe model output and hazard data into how we quote.
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• Partner on policy forms and endorsements for our own paper, from causes of loss to valuation and deductible terms.
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• Own the property loss ratio, mix, and rate adequacy, and adjust appetite and pricing as results and catastrophe experience come in.
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• Support risk and portfolio management across the property book: manage accumulation by peril and zone, set concentration limits, and bring probable maximum loss and aggregate views to reinsurance and capital decisions.
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• Hire and lead property underwriters as the book scales.
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Who You Are

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• 5+ years underwriting commercial property with real authority, and you've owned a book and its results.
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• You've set appetite and written property underwriting guidelines.
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• You're fluent in COPE, statements of values, insurance-to-value, and catastrophe model output, and you know when the model is wrong.
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• You enjoy building on a small, fast-moving team. If your instinct is to schedule a meeting about scheduling a meeting, this isn't the right fit.
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Nice to Have (Not Required)

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• E&S property experience, including catastrophe-exposed risks.
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• Builders risk or inland marine experience.
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• Experience working closely with SWEs.
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• CPCU or a similar designation.
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Why Join

Ground Floor Ownership. You're not property underwriter number 40 at a carrier where appetite gets set three committees up. You own the property book from day one, and meaningful early-stage equity reflects that.

Build It From Zero. Build the property underwriting function, the guidelines, and the team from the ground up.

Speed. Work directly with founders and SWEs who can ship what you design, fast. What you design becomes working product, not a PDF in a shared drive.

Founder-Led Culture. Many on the team are ex-founders. We care about results, ownership, and hunger. Your title matters less than what you ship.