Jerry.ai is building the first app to manage all your physical assets: starting with your car, then home, and motorcycle, etc.
Our insurance marketplace is our core product today, we help people save time and money on insurance shopping (including car, home, etc). Now, we are expanding into broader problems that make owning a car expensive, confusing, and stressful. The next chapter: being helpful every time someone drives.
We have raised $240M, grown revenue 60X in six years, reached 5M customers, and built a team from some of the best consumer and technology companies in the world.
Why we’re hiring this role
DriveShield is one of our big product bets to make Jerry useful not just when someone shops for insurance, but every time they drive. DriveShield helps drivers track trips, understand their driving score, earn points, get personalized safety tips, build better habits, and even reduce risk of collisions. The opportunity for this is huge, but the challenge is: most people don’t wake up excited to check their driving behavior data. Driving scores can be confusing. Safety advice can be unhelpful. Rewards can feel arbitrary. If the experience is not clear, motivating, and trustworthy, people won’t care.
We need a Senior Product Manager who can turn DriveShield from a useful feature into a daily habit for millions of drivers.
Why you will (or won’t) like the work
You will own a real behavior-change problem. Your job is to make drivers care, come back, and improve.
You will be hands-on. You will work deeply in product, data, UX, research, and experimentation.
This category is not inherently “sexy”. Insurance and driving safety are not things people think about everyday, only when something bad happens and it’s too late. Your job is to help them before something goes wrong, and the potential for impact is huge.
The roadmap will not be handed to you. You will find the highest-leverage problems, build conviction, and ship.
The bar is high. You will work with a talent-dense team from companies like Nvidia, LinkedIn, DoorDash, Amazon, Klarna, and Lemonade.
The upside is huge. Jerry has raised $240M, grown revenue 60X in five years, reached 5M customers, and is building toward 50M.
What you’ll own
Your mandate is to make DriveShield clearer, more motivating, and more valuable — measured through adoption, engagement, retention, and trust.
Make DriveShield a habit: Own the journey from first trip to next action: understanding a score, seeing what changed, earning points, getting guidance, and feeling motivated to drive safer.
Improve the core experience: Modernize trip tracking, driving scores, points, safety tips, progress, and guidance. The goal is not prettier screens. It is an experience that is easier to understand, trust, and return to.
Build engagement loops that feel useful: Figure out what makes drivers come back after a trip: sharper score explanations, better notifications, personalized insights, clearer rewards, new habit mechanics, or new links between safer driving and savings.
Explore what DriveShield becomes next: Help define new safety and mobility capabilities, including smarter insights, crash detection, partner integrations, build-vs-buy opportunities, and AI-powered personalization.
Learn fast from users and data: Use analytics, research, usability studies, prototypes, and A/B tests to understand what works. Move quickly, but not blindly.
Who you are
A consumer product craftsperson. You know that tiny UX decisions can decide whether users trust or abandon a product.
A behavioral product thinker. You care about why people form habits, ignore advice, respond to rewards, or distrust scores.
A detective. You do not stop at “engagement is down.” You find where users dropped, what they saw, and why it happened.
Data-driven, not data-obedient. You can build conviction from messy signals and use experiments to learn quickly.
High-bar and detail-oriented. You notice vague copy, confusing product experiences, missing instrumentation, edge cases, and UX that functions but doesn’t feel delightful.
A strong collaborator. You bring Design, Engineering, Data, Research, Growth, and business partners with you, prioritizing expertly to balance speed and quality.
Comfortable with unglamorous problems. You care about solving real consumer problems in a category that affects almost everyone.
Ideal experience
Consumer product experience across mobile or web.
Work on engagement, retention, personalization, lifecycle, rewards, or habit formation.
Strong partnership with Design, Research, Engineering, and Data.
Comfort with funnel analysis, experiments, and ambiguous user behavior.
Experience in trust-sensitive categories like mobility, insurance, fintech, marketplaces, safety, health, or personal finance.
Startup or fast-paced 0 to 1 experience is a plus.
Jerry is building the first super app for car ownership. We help people save money on car insurance today, and we are expanding into the broader problems that make owning a car expensive, confusing, and stressful.
We have raised $240M, grown revenue 60X in five years, reached 5M customers, and built a team from some of the best consumer and technology companies in the world. DriveShield is one of the product bets that can make Jerry useful not just when someone shops for insurance, but every time they drives.
While we appreciate your interest and application, only applicants under consideration will be contacted.
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 removed]_](mailto:[email removed])
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
Jerry.ai is America’s first and only super app to radically simplify car ownership. We are redefining how people manage owning a car, one of their most expensive and time-consuming assets.
Backed by artificial intelligence and machine learning, Jerry.ai simplifies and automates owning and maintaining a car while providing personalized services for all car owners' needs. We spend every day innovating and improving our AI-powered app to provide the best possible experience for our customers. From car insurance and financing to maintenance and safety, Jerry.ai does it all.
We are the #1 rated and most downloaded app in our category with a 4.7 star rating in the App Store. We have more than 5 million customers — and we’re just getting started.
Jerry.ai was founded in 2017 by serial entrepreneurs and has raised more than $240 million in financing.
Join our team and work with passionate, curious and egoless people who love solving real-world problems. Help us build a revolutionary product that’s disrupting a massive market.
About Jerry
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.
