Head of Captive Finances

At Corgi, we're building the first fully automated insurance carrier. Our goal is to rebuild the $1T+ insurance industry from the ground up using AI. We’re not just building a company; we’re building infrastructure for the next hundred years. If you’ve built things from scratch and know what it means to move fast and own outcomes, we want you on the team. We’re well-funded and backed by top investors, providing the resources you wish you had when building your own business. We don’t care about traditional roles or titles—just that you’re smart, proactive, and bring founder-level ownership and drive to help us build something massive. The Role

We’re looking for a

Head of Captive Finances

to join our growing finance and insurance operations team. You’ll be responsible for supporting the formation, administration, and compliance of captive insurance entities under Corgi’s management. This is not a traditional back-office role. You’ll be deeply involved in automating the end-to-end captive management process—from regulatory filings to financial reporting—and will collaborate with engineering and finance to design the next generation of captive management infrastructure. The ideal candidate has a strong understanding of insurance accounting, regulatory filings, and compliance, combined with a builder mindset. Whether you’ve worked at a captive manager, public accounting firm, or insurance carrier, this role offers the opportunity to take that experience and help modernize an entire industry segment. What You’ll Do

Assist in the formation and ongoing management of captive insurance entities, including compliance with domicile regulations Support preparation and filing of NAIC and state regulatory reports, including quarterly and annual statements Coordinate audits, actuarial reports, and regulatory examinations for captives under management Prepare and review financial statements, premium calculations, and policyholder documentation Maintain general ledgers, reconciliations, and journal entries for multiple captives Manage correspondence with regulators, auditors, and other external stakeholders Partner with engineering to design and test tools for automated financial reporting, regulatory filings, and compliance workflows Help establish internal control frameworks, policies, and scalable operational processes as we expand our captive portfolio What We’re Looking For

Bachelor’s degree in Accounting, Finance, Risk Management, or related field 1–3 years of experience in captive management, insurance accounting, or public accounting (audit or insurance clients preferred) Strong understanding of U.S. GAAP and Statutory Accounting Principles (SAP) Ability to work through legal texts Excellent organizational and analytical skills with strong attention to detail Comfortable working in a fast-paced, high-growth environment Excited by the idea of building systems and automating traditional insurance workflows Nice to Have’s

CPA, ACI, ARM, or equivalent professional certification (or progress toward one) Experience working with or for captive insurance managers, risk retention groups, or insurance carriers Exposure to fintech, insure tech, or automation tools for finance and compliance Prior experience preparing NAIC or domicile-specific filings (e.g., Vermont, Delaware, Utah) Understanding of reinsurance structures, fronting arrangements, and risk pooling Familiarity with NAIC regulatory filing requirements and domicile-specific reporting standards Why Corgi

You’ll be joining a small, elite team at the intersection of finance, insurance, and technology, building the foundational infrastructure for the next century of insurance. You’ll work directly with experienced finance, legal, and engineering leaders and gain exposure to the entire lifecycle of insurance operations in a modern, automated environment.

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