Head of Compliance & Regulatory Affairs

Job Description

At Corgi, we're building a full stack AI insurance platform. 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. Insurance is one of the most heavily regulated industries in the country, and as we scale across states, and toward potential public-company status, we need someone who can build a world-class compliance and regulatory function. We're well-funded and backed by top investors, providing the resources you wish you had when building your own program. We don't care about traditional roles or titles - just that you're smart, proactive, and bring ownership and drive to help us build something massive. If you've spent your career protecting companies from the inside, designing controls, navigating regulators, and giving leadership the clear-eyed counsel that keeps a business out of trouble, we'd love to talk to you.

What You'll Do

As our Head of Compliance & Regulatory Affairs, you will report directly to our General Counsel, Peter Skaliy, and own the company's compliance program, regulatory strategy, and risk advisory function. This is a strategic, management-track role you'll be designing the framework, advising leadership, and working with counsel on contested matters.

Key Responsibilities

• Design, build, and lead Corgi's enterprise compliance program: policies, procedures, training, monitoring, and reporting.
• Own state insurance regulatory compliance: licensing, market conduct, rate and form filings, financial reporting, and examination readiness across all jurisdictions where we operate.
• Advise leadership and the board on securities matters as we scale — including disclosure controls, insider trading policies, and IPO-readiness work.
• Partner with the General Counsel and the executive team on corporate governance: board and committee processes, charters, codes of conduct, and ethics policies.
• Build and oversee data privacy and information security compliance (GLBA, CCPA, GDPR where applicable, and state-level frameworks).
• Lead AML/KYC, sanctions, anti-fraud, and consumer protection programs appropriate to a digital insurance carrier.
• Proactively identify regulatory and reputational risk; design controls and remediation plans to mitigate them before they become problems.
• Manage relationships with regulators, examiners, and external advisors; serve as a senior point of contact for inquiries and exams.
• Direct and supervise outside counsel on regulatory investigations, enforcement matters, and contested proceedings without serving as front-line litigation counsel.
• Provide strategic risk advisory to the CEO and leadership team on new products, market expansion, M&A, and corporate transactions.

What We're Looking For

• JD from an accredited law school (or equivalent compliance credential); active bar license in good standing.
• 8+ years of combined experience in regulatory, compliance, or corporate counsel roles, ideally with meaningful securities, or financial-services regulatory exposure.
• Track record building or significantly scaling a compliance function — preferably in insurance, fintech, or another regulated industry.
• Sophisticated judgment, excellent written and verbal communication, and the ability to distill complex regulatory risk for non-legal stakeholders.
• Comfortable operating at the intersection of strategy, governance, and risk; energized by ambiguity and rapid change.
• Strong leadership and program-building instincts: you've designed controls and processes from scratch, managed external advisors, and mentored junior team members.

Why You Should Join

• Strategic Seat at the Table: You'll report to the General Counsel and partner with the executive team on the decisions that will define the company for decades — not just review them after the fact.
• Build, Don't Inherit: This is a ground-floor opportunity to design a compliance and regulatory program for a category-defining company, with the resources and executive support to do it right.
• Impact & Speed: Work in a fast-paced environment where your contributions will have immediate, tangible effects on the company's success.