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Head of Specialty Product & Underwriting

Business
Corgi
Department
Product
Location
Chicago, IL
Workplace
On-site
Employment
Full-time
Pay
$150K – $300K
Experience
6+ years

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.

ForbesAs covered in Forbes, May 2025.
The Economic TimesAs covered in The Economic Times, Jul 2025.
Insurance BusinessAs covered in Insurance Business, Jan 2026.
The Wall Street JournalAs covered in The Wall Street Journal, Sep 2025.
Inc.As covered in Inc., Sep 2025.
ForbesAs covered in Forbes, May 2025.
Insurance BusinessAs covered in Insurance Business, Jan 2026.
Inc.As covered in Inc., Sep 2025.
The Economic TimesAs covered in The Economic Times, Jul 2025.
The Wall Street JournalAs covered in The Wall Street Journal, Sep 2025.
Corgi

Coverage may be underwritten by affiliated or partner insurers, including Corgi Insurance Company, Inc., a property and casualty insurance carrier (NAIC #17989).

Certain coverages may be underwritten by risk retention groups, which are state-chartered insurance companies that provide liability coverage to their members pursuant to the Liability Risk Retention Act (15 U.S.C. § 3901 et seq.).

Corgi Insurance Services, Inc. is a licensed insurance producer (CA License #6012791) and acts as program administrator, not as the insurer.

Certain coverages may be available through partner insurers that are admitted in the applicable state and rated A- (Excellent) or better by AM Best. Availability varies by state, line of business, and risk characteristics. Not all coverages are available through every insurer.

Coverage is subject to underwriting approval. Availability varies by jurisdiction, and not all products are available in all states. Limits, retentions, and terms shown on this page are illustrative and may differ from your actual policy. Review your complete policy packet, including declarations, policy forms, endorsements, and accompanying disclosures, for the issuing insurer, coverage terms, conditions, limitations, exclusions, and applicable notices. Your policy documents govern coverage. See our Disclaimers page for full licensing and insurer information.

Securities products and services are offered through ANOS Capital, LLC, a registered broker-dealer and member of FINRA and SIPC, registered with the MSRB, and a subsidiary of Corgi Insurance Services Inc. Corgi Insurance Services Inc. is not a registered broker-dealer or investment adviser. Insurance products are offered through Corgi Insurance Services, Inc. and are not securities.

Corgi ETFs are distributed by Paralel Distributors LLC, which is not affiliated with ANOS Capital. Investing involves risk, including loss of principal. Options involve risk and are not suitable for all investors. For the Options Disclosure Document, contact info@anoscap.com.

Testimonials and customer figures relate to Corgi's insurance services only. Check ANOS Capital on BrokerCheck.