Head of Specialty Product & Underwriting

Corgi Insurance

Corgi is building an AI financial infrastructure company

Head of Specialty Product & Underwriting $150K - $300K • Chicago, IL, US Job type Full-time Role Product Experience 6+ years Visa US citizen/visa only

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About the role

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.

Our E&S program is live and the first book is flowing. Now we need someone to own it.

The Role

As Head of Specialty Product & Underwriting, you'll own Corgi's E&S book end to end. You'll set appetite, write the guidelines, shape the products, and be accountable for how the book performs. You'll work side by side with our software engineers and product team to turn underwriting judgment into forms, rating logic, and workflows that let us quote and bind at a speed the market hasn't seen.

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 Own

Appetite and guidelines: Define what we write, where, and on what terms. Write and maintain underwriting guidelines, authority levels, and referral rules as the book grows.

Product: Shape coverage across our E&S lines. Partner on policy forms, endorsements, and filings for our own paper.

Rating and pricing: Work with software engineers and actuarial resources to build and refine rating logic, and make sure what the system produces reflects sound underwriting.

Risk and portfolio management: Support portfolio strategy by tracking exposure, concentration, and aggregation across the book, and help shape reinsurance and risk decisions as we scale.

Book performance: Own loss ratio, mix, rate adequacy, and growth. Monitor results, spot trends early, and adjust appetite and pricing accordingly.

Team: Hire and lead underwriters as the book scales, and set the standard for how underwriting is done at Corgi.

You'd Be a Great Fit If You

Have 5+ years in commercial E&S and have owned a book and its results

Have set appetite and written underwriting guidelines

Bring strong wholesale broker relationships

Enjoy building on a small, fast-moving team

Bonus Points If You

Have worked closely with software engineers or a rating engine

Why Corgi

Own a live E&S book from day one at a carrier built on modern infrastructure

Build the underwriting function, the products, and the team from the ground up

Work directly with founders and engineers who can ship what you design, fast

Meaningful early-stage equity in a company rethinking how insurance gets written

Location

Chicago, in office.

Compensation

$150,000 - $300,000, equity included.

About Corgi Insurance

Corgi is a full-stack insurance carrier building better, faster insurance products for startups. We’re not a broker, so we underwrite and issue policies directly, with fewer handoffs and less friction. Cutting out intermediaries lets us tailor coverage to how companies actually operate and price risk more efficiently.