AI Product Engineer

Jerry.ai is a profitable, Series C, YC-backed tech startup with 5M+ customers and $240M in funding. We’re building the first AI-powered advisor to manage all your physical assets. We started with car insurance in 2019, now we’re expanding into new verticals (e.g. home, motorcycle, RV, boat) and accelerating our growth.

The opportunity is massive — car insurance alone is a $300B market in the U.S. We spent the last few years building our supply (we work with 100+ insurance carriers) and our technical infrastructure (60% of policies today are sold automatically without human intervention, 90% of inbound customer inquiries are resolved via AI and automation). The next chapter is about accelerating our growth — going from 5M to 50M customers by 2030.

Our insurance marketplace is our core product today, and our ability to automate the end-to-end shopping experience is our core differentiator. The AI & Automation team owns the most critical part of that – how we automate the entire insurance quoting experience for our customers and orchestrate complex, multi-step transactions with external insurance provider systems to finalize policy purchases.

Before off-the-shelf AI agents existed, we built our own proprietary infrastructure to scale automated insurance purchases and customer support. Today, 60% of insurance policies are sold automatically without human intervention, and 78% of inbound customer inquiries are resolved via AI and automation, with 83% reporting a positive experience.

Our current system is working but our use cases are rapidly growing as our business expands beyond car insurance and available AI models are also evolving. We need someone to lead the charge in building our “next generation” AI system, including building new automations for things like document validation (drivers’ licenses, proof of insurance, etc), voicebot expansion into stateful, phone-based interactions, and enable our bots to have direct external system navigation to resolve complex issues more quickly and accurately than human agents.

• Our AI agents and automation system, which has two components:

• 5+ years in software engineering, ideally at an early-stage startup where you’ve owned outcomes end-to-end.

• You are a builder at heart. You don't need someone else to write the spec.

• You've tinkered with a new model within days of its release, and you can explain why one architecture or approach is superior to another.

• Experience putting LLM-based systems into production, including the unglamorous parts: evals, regressions, latency, cost, and failure-handling.

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.