Your car and your home are your most important assets, yet the experience of owning one is stuck in the 90s. Every part of the journey (buy/sell, insurance, maintenance/repairs, etc) is fragmented, complicated, and expensive.
Jerry.ai is building the first app to manage it all. We started with your car ($2T market in the U.S.) — launched car insurance in 2019, became one of the top 3 brokers in the country, then added driving insights, diagnostics, and a repair marketplace.
We've reached 5M+ customers, raised $240M+, and scaled our revenue 80X (since our app launch in 2019). And we've been profitable since 2024.
We’re now ready to expand beyond car ownership into adjacent verticals (home, motorcycle, RV, etc) to manage all of your physical assets in one place. You will own one of these new bets from 0-1.
This is not a pure strategy role. You will be hands-on, standing up a new business line, including scoping/sizing a new market, research and analysis, building a new product, leading go-to-market, testing and iterating, and eventually, building a team to scale it.
Phase 1: Ramp on existing products. For the first few months, you will join an existing product team, and learn how we think about and develop products. You will learn how to conduct customer research, write product specs, work with engineers and designers, use tools like Figma and Codex to prototype, design and run experiments, analyze outcomes, and incorporate learnings into iterative product decisions.
Phase 2: Build a new business. Take one of our target verticals (e.g. commercial auto insurance, property tax, RV insurance, etc) from concept to a revenue-generating product. Run the incubation, build and ship the product, test and iterate, and then hire a team to run it.
An entrepreneur at heart. You want to learn how to build a business from the ground up, and how to scale it.
Tolerance for ambiguity. You’re comfortable making decisions with incomplete information and pivoting quickly as your understanding evolves.
Deeply curious. You are fascinated by the “why” behind customer behaviors and market dynamics.
Data-obsessed. If a funnel drops 2% or an A/B test returns an unexpected result, you dive immediately into the analysis to figure out the root cause. And you aren’t satisfied until you understand what really happened.
5+ years experience at a consulting firm, investment bank, high-growth startup or equivalent.
Track record of independently owning ambiguous problems and delivering outcomes.
Strong analytical skills; comfortable running data analysis in SQL, Excel or Python.
Experience juggling multiple complex work streams without letting anything drop.
Comfort and ability to interface with executive stakeholders on a daily basis.
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 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
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.
Compensation Range: CA$170K - CA$220K
