Why you should join us
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 the car in 2019, now we’re expanding into new verticals (e.g. home, motorcycle, RV, boat) and accelerating our growth.
About this role
We’re at an inflection point in our journey. After 2 years of profitable growth with a stable core business(car insurance marketplace), we’re ready to expand our product offeringsand accelerate customer growth.
We’re looking for 2-3 Product Managers to drive progress across one of our key new product bets, including motorcycle insurance(just launched), home insurance(also just launched), new insurance products for other assets like boatand RV(concept phase, as well as non-insurance products to make carand home ownership easier such as helping customers save money on their property taxes(about to launch.
Each of these new product areas comes with its own operational complexity, its own customer personasand painpoints,and its own path to scale. And we’re looking for builders who are excited to take ownership of one of these new bets.
Why You Will (Or Won’t) Like Working Here
0-to-1 scope: The products you will work on are new territory for us. There are no established frameworks, no prior PM who has figured it out.
Product complexity: Property tax rules vary county by county. Specialty vehicle insurance involves regulatoryand product complexity that doesn’t exist in standard auto. These are not clean, well-scoped problems to solve.
Real impact: You will have meaningful ownership. And what you do will likely materially impactthe trajectory of our business over the next few years.
What you’ll own
There are several new product bets inthe motion. The specific product you will work on will largely depend on your prior experience, interests/preferences,and our business priorities when you jointhe team.
The goalin every case remainsthe same: ramp quickly on a new domain, distill dataand insights to identifythe highest leverage areas to prioritize(including quantitative data from our Data Science teamand qualitative data from our Customer Insights & Research team), buildand ship new products, get customer feedback quickly, apply learningsand iterate,and compound on what works.
Whether it’s home, motorcycle, boat or RV products, you will be a key contributor to our product roadmapand own execution from early concept or early launch to finding product-market fit,and scaling.
Who you are
A first-principles thinker: You approach problems with curiosityand use data to develop clear hypotheses before you reach for a solution. You’re analytically strong but your instinct is to ask “what are we trying to solve here?” before jumping to “what should I build?”
An owner: You act like your name is on the door. If something is broken, you feel responsible for fixing it, even if it’s outside of your swim lane.
Empathetic & Curious: You care deeply about understanding what drives how they think, feel and behave.
Diligent: Your follow through is impeccable. When you own something, nothing falls throughthe cracks.
What you bring
5+ years in management consulting(MBB or equivalent), consumer-facing product management, or equivalent role at a high-growth startup
Consumer product instincts, either from direct product building experience or from close work alongside consumer product teams
Comfort with data: able to run your own analysisand build conviction from messy signals
We offer a comprehensive benefits package to regular employees, including health, dental,and vision coverage, paid time off, paid parental leave, 401(K) plan withemployer 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
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 ofthe life you’ve worked hard to build. Yetthe experience of owning them is stuck inthe 90s. Every step ofthe 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 youthe right car or home atthe right price, lock inthe best insurance rate without you lifting a finger, remind you before that service appointment turns into an expensive repair,and help you sell atthe best price whenthe time is right. That friend is Jerry.
We started with car insurancein 2019, became one ofthe top 3 brokers inthe U.S., then added driving insights, diagnostics,and a repair marketplace. We’ve reached 5M+ customers, raised $240M+,and have been profitable since2024. We’re now expanding into home, motorcycle, RV,and beyond.
Led by serial entrepreneursand 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 Jerryand stay — we are a smalland mighty team of competitive but kind people who thinkand act like owners, care deeply aboutthe qualityand impact of our work,and are relentless in our pursuit of learningand mastery over our craft.
We are proud to consistently rank as one of Y Combinator’s Top Companies, Forbesand Statista’s Best Startup Employers,and to have received other accoladesin fintechand insurtech innovation, workplace culture,and leadership.
We are a remote-first company, but if you prefer in-person or hybrid, we also have officesin Palo Alto, New York City, Chicago,and Toronto.
