Remote Sports Modeling Jobs in Chicago, IL (NOW HIRING)

Location: London, UK or Remote (US)

Compensation: $150,000–$250,000 (US) or £100,000–£200,000 (UK), total compensation including equity

About Corgi

Corgi is a full-stack insurance carrier building better, faster insurance products from the ground up. We're not just a broker: we design, underwrite, price, and issue policies directly, with fewer handoffs and less friction. Insurance is the largest unautomated industry in financial services, and we're rebuilding it using AI. We've raised $374M from Kindred, TCV, and others at a $2.6B valuation to do so. YC S24.

The Role

We're looking for a Head of Sports Underwriting to own our sports book – pricing, appetite, wordings, and referrals. We're the carrier, not a broker and not an MGA fronting for someone else, so what you decide is what actually happens. The book is still small today – mostly P&C, like general liability, participant liability, D&O, and abuse & misconduct, plus some smaller contingency and A&H lines. We write it for national governing bodies (NGBs), professional teams, and events, and we want to grow it substantially from here.

The ideal candidate can do all of this, not just price it or just write the wording, or has a strong base and is willing to learn quickly. You'll have a real say in pricing, policy design and wording, appetite, and risk selection. Our underwriting runs on an AI-native stack, which empowers our underwriters to have 10x more impact.

What You'll Do

• Own risk selection, pricing, and appetite across NGBs, professional teams, and events.

• Shape policy design and wording, not just the rate.

• Codify your judgment into rating models, appetite rules, and referral logic.

• Review referrals and complex risks, and feed every decision back into the system.

• Build and lead the sports underwriting team from the ground up as the book scales.

What We're Looking For

• 4+ years underwriting sports, leisure, or entertainment risks at a carrier, MGA, or Lloyd's syndicate – this is a specialist seat, not a generalist one.

• Strong P&C fundamentals across liability lines.

• Fluency in sports exposure: sanctioned events, club and NGB structures.

• Well-rounded: credible on pricing, wordings, appetite, and risk selection.

• Comfortable operating in a fast-moving, ambiguous environment.

Nice to Have

• Contingency or A&H exposure alongside your P&C book.

• Experience building rating plans, appetite frameworks, or underwriting guidelines from scratch.

• Experience hiring and leading underwriters.

Why Corgi

• Take an early-stage book to scale and own the team behind it.

• Underwrite on our own paper – no fronting carrier's appetite to work around.

• Build the models and rules that underwrite every sports risk we write.

• Work with us directly, not through layers of management.

• Competitive compensation, equity, and benefits.

Compensation Range: £100K - £200K