Director, Workers' Underwriting

Location: Chicago, IL (Flexible within the United States)

Experience: 4-7+ years

Corgi is building the next generation of financial institutions. We’re rethinking how insurance, financial products, and other complex financial services are built and operated from the ground up.

Corgi is a licensed insurance carrier with several property and casualty (P&C) lines of business, and we are expanding into additional lines. We’re building modern insurance products and operating systems from the ground up, combining deep insurance expertise with technology to make insurance work better.

We move quickly, work across disciplines, and expect people to take meaningful ownership from day one. Our teams are small, ambitious, and highly execution-oriented.

We are looking for an experienced Workers’ Compensation insurance professional to help build Corgi's Workers’ Compensation business and take ownership of important underwriting decisions.

This role is a strong fit for a senior Workers’ Compensation leader who has owned underwriting results and wants to build a business from the ground up. You should be comfortable leading broker, regulator, and cross-functional relationships across the full underwriting lifecycle.

You will help define the overall underwriting strategy for the business, establish the appropriate controls and governance, and build the team and infrastructure required to operate a sophisticated Workers’ Compensation insurer.

This is a hands‑on role for someone who understands the Workers’ Compensation lifecycle and wants to help shape how a new business is built from the ground up.

• Lead the development of Corgi's Workers’ Compensation underwriting strategy.
• Establish underwriting appetite, guidelines, authority structures, and risk controls.
• Develop frameworks for pricing, risk selection, reserving, portfolio management, and profitability.
• Help establish appropriate state-by-state underwriting and operational processes.
• Work with actuarial, regulatory, legal, claims, and finance teams on the development of the business.
• Develop relationships with regulators, reinsurers, brokers, and other industry stakeholders.
• Evaluate complex Workers’ Compensation risks and provide senior underwriting judgment.
• Establish portfolio monitoring and performance-management frameworks.
  
  Help recruit and develop the initial Workers’ Compensation team.
• Serve as a senior subject‑matter expert across the organization.

• 4-7+ years of Workers’ Compensation experience, including senior underwriting leadership.
• Several years of hands‑on Workers’ Compensation underwriting experience, ideally at a carrier or specialty insurer.
• Deep knowledge of multi‑state Workers’ Compensation markets.
• Experience with NCCI and independent rating bureau states (e.g., California, New York, Pennsylvania), and familiarity with monopolistic‑fund states.
• Experience across guaranteed cost, large deductible, and other loss‑sensitive programs.
• Strong understanding of pricing, underwriting, claims, reserving, and portfolio economics.
• Experience working with regulators and other external stakeholders.
• Strong communication skills and the ability to build trust with brokers and internal partners.
• Ability to operate at both the strategic and technical level.

• Experience taking ownership of a book, underwriting initiative, or cross‑functional project.
• Experience at a leading Workers’ Compensation carrier such as Travelers, The Hartford, AmTrust, Zurich, Chubb, Berkshire Hathaway (GUARD / BHHC), Liberty Mutual, or ICW Group.
• Deep regulatory and state‑market knowledge.
• Track record of building, growing, or turning around a Workers’ Compensation book.
• Experience with trucking and transportation…