Jobs at Jerry (Now Hiring) — 96 open — Page 3

Why We Exist

Your car and your home are your most important assets, yet the experience of owning them is stuck in the 90s. Every part of the journey - insurance, repairs, financing, maintenance - is fragmented, complicated, and expensive. Jerry.ai is building the first app to manage it all.

We started with car insurance in 2019, became one of the top three brokers in the country, then added driving insights, diagnostics, and a repair marketplace. We've reached 5M+ customers, raised $240M+, scaled revenue 70X, and became profitable in early 2024.

Why we’re hiring this role

We are fundamentally changing the way people think about and shop for insurance. And 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 and becoming a $10B business by 2030.

The Growth team owns the entire customer sign-up and purchase funnel for our car insurance marketplace (our core product today), and drives how millions of people discover, evaluate, and become a Jerry customer.

Our funnel is healthy (we're profitable at 5M customers), but our product is becoming increasingly complex as we onboard new insurance carriers and expand beyond car insurance. As a result, our Growth team is expanding, and we need a Product Manager who can take on product walkthroughs, user feedback synthesis, new feature builds, product launches, and funnel improvements as we continue growing.

Why You Will (Or Won't) Like Working Here

• Direct exposure: You'll report directly to our VP of Growth with visibility to the c-suite team. You'll have visibility into product strategy, business model tradeoffs, and roadmap decisions from Day One.

• Time zone constraint: The engineering team is partly based in China. You'll need to maintain 3–4 hours of daily overlap with China business hours. This is a real constraint on your schedule, and it's non-negotiable.

• Small team: The Growth team has 3 Product Managers (including you) and the surface area is huge, which means you'll have to be scrappy, but also that you'll have lots of scope and ownership.

• Fast shipping culture: We run weekly sprints. Products that take 6-12 months to ship elsewhere, we launch in 1-2 months. This means faster learning and faster growth, but also a more demanding environment.

What You'll Own

• Phase 1: In your first few months, your job is to learn how to be a product manager and develop a deep, ground-level understanding of how our funnels perform. You'll conduct structured product walkthroughs to map user journeys and identify friction points. You'll own user feedback monitoring: pulling signals from reviews, support tickets, and research and turning them into actionable insight. And you'll drive bug triage and resolution with engineering, making sure quality issues are prioritized and closed.

• Phase 2: As you build context, you'll start leading end-to-end delivery of product initiatives starting with well-scoped launches like landing pages and compliance-driven features, then expanding from there. You'll also contribute to A/B testing and experiment design, partner with Design and Engineering to ship experiences that balance speed, clarity, and trust, and help translate ambiguous customer problems into clear hypotheses and requirements.

Who You Are

• Structured problem solver: You’re comfortable breaking ambiguous problems into clear hypotheses before reaching for a solution, as well as working with incomplete information.

• Diligent: Your follow through is impeccable. When you own something, nothing falls through the cracks.

• Curious about customer psychology: You find customer feedback intrinsically interesting and not some box to check. You care deeply about understanding what drives how they think, feel and behave.

• Strong communicator: You can work effectively across engineering, design, analytics, and marketing, including across time zones. You calibrate how much context others need and give it clearly.

What You'll Bring

• 2+ years of experience in management consulting, product management, or product/business operations

• Strong analytical skills; ability to pull, structure, and interpret data independently.

• Track record of owning ambiguous problems and delivering impact.

• Strong written and verbal communication skills, including the ability to synthesize messy signals into clear recommendations

• Willingness to maintain regular daily overlap with China business hours for engineering coordination

While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.

Please note: Jerry.ai is only able to hire full-time salaried employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada, and full-time hourly employees who currently reside in AZ, FL, GA, NV, NY, NC, TN, TX, UT, or VA. Unfortunately, we cannot accept applications from candidates residing elsewhere at this time.

Jerry.ai is proud to be an Equal Employment Opportunity employer. We prohibit discrimination based on race, religion, color, national origin, sex, pregnancy, reproductive health decisions or related medical conditions, sexual orientation, gender identity, gender expression, age, veteran status, disability, genetic information, or other characteristics protected by applicable local, state or federal laws.

Jerry.ai is committed to providing reasonable accommodations for individuals with disabilities in our job application process. If you need assistance or an accommodation due to a disability, please contact us at [email protected]

The successful candidate’s starting pay will fall within the pay range listed on this job posting, determined based on job-related factors including, but not limited to, skills, experience, qualifications, work location, and market conditions. Ranges are market-dependent and may be modified in the future. In addition to base salary, the compensation may include opportunities for equity grants.

We offer a comprehensive benefits package to regular employees, including health, dental, and vision coverage, paid time off, paid parental leave, 401(K) plan with employer matching, and wellness benefits, among others. Equity opportunities may also be part of your total rewards package. Part-time, contract, or freelance roles may not be eligible for certain benefits.

About Jerry.ai

Your car and your home are your most expensive assets. And for most people, these 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 or, worse, an accident, and help you sell at the best price when the time is right. That friend is Jerry.

Jerry is building the first AI agent to manage all your physical assets. 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 have been profitable since 2024. We're now expanding into home, motorcycle, RV, and beyond.

We’re fully remote with offices in Palo Alto, New York, Chicago, and Toronto.