Insurance Compliance & Regulatory Senior Lead

Jerry is the #1 rated app for car owners. We help over 5 million people save money on insurance, repairs, and loans—all in one place. Since 2019, we’ve become one of the fastest-growing tech companies in the U.S.

We are looking for an Insurance Compliance & Regulatory Senior Lead to join our Insurance Operations team. Reporting directly to our Senior Manager of Insurance Ops, this role is ideal for an experienced insurance operations leader who excels at solving complex systemic issues, building rigorous compliance frameworks, and acting as the strategic bridge between our customers, carrier partners, state regulators, and internal product teams.

Jerry is building the first AI-powered advisor to manage all your physical assets.

Your car, home, and motorcycle aren't just purchases, they're the physical embodiment of the life you've worked hard to build. Yet the experience of owning them is stuck in the 90s. Every step of the journey — buying, insuring, maintaining, repairing, selling — is fragmented, complicated, and expensive.

Imagine having a trusted friend in your pocket who takes care of everything: they find you the right car or home at the right price, lock in the best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair, and help you sell at the best price when the time is right. That friend is Jerry.

We started with car insurance in 2019, became one of the top 3 brokers in the U.S., then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, and achieved profitability in 2024. We're now expanding into home, motorcycle, RV, and beyond.

Led by serial entrepreneurs and backed by Y Combinator, our team comprises talented and big-hearted leaders from places like Nvidia, Meta, Amazon, BCG, McKinsey, Bain, and GEICO. Our culture is the #1 reason people join Jerry and stay — we are a small and mighty team of competitive but kind people who think and act like owners, care deeply about the quality and impact of our work, and are relentless in our pursuit of learning and mastery over our craft.

We are proud to consistently rank as one of Y Combinator's Top Companies, Forbes and Statista's Best Startup Employers, and to have received other accolades in fintech and insurtech innovation, workplace culture, and leadership.

We are a remote-first company, but if you prefer in-person or hybrid, we also have offices in Palo Alto, New York City, Chicago, and Toronto.