Jerry
Overview
You could work anywhere. Jerry is building the first AI-powered assistant to make car ownership accessible and affordable for 80% of Americans who rely on it daily — from buy/sell to insurance, financing, safety, maintenance and repairs, we’re reimagining the entire ecosystem. This is a $2T problem and a difficult one to solve. Today, over 5M Americans trust us to take care of their insurance shopping, maintenance and safety, and we’re just getting started. We launched our app in 2019, reached profitability in 2024, and are on track to become a $10B company by 2030. Millions of people rely on Jerry to make buying, owning and maintaining their car easier and more affordable. We want Jerry to feel like a trusted friend in your pocket — someone who handles the hard parts, explains things clearly, and has your back when it matters most. Design is how that vision comes to life. As one of the first designers on the team, your work will directly shape how Jerry looks, feels, and works at scale. You’ll influence not only what we build next, but also our bar for design that will define Jerry for years to come. What You’ll Work On
Drive measurable gains in user engagement and onboarding across Jerry’s core offerings (shop, safety, repairs) by crafting delightful, friction-less experiences. Ship 0→1 features that modernize car care for the everyday car owner. Conduct and synthesize user research (qual + quant), rapidly prototype in Figma, and validate solutions with usability testing and A/B experiments. Raise the UX quality bar across the board: clarity, speed, and consistency. Thoughtfully apply AI to make Jerry faster, clearer, and more helpful. Who You’ll Work With
Art Agrawal (CEO & Head of Product) — your direct manager until we hire our first Head of Design. Patrick Westwood (Founding Designer) who has already taken Jerry from 0 to 5M users. A broader product org of 11 product managers, 55 engineers, and 12 product analysts/data scientists, all driven to build the best-in-class consumer experience. What We’re Looking For
A portfolio that demonstrates strong visual taste, thoughtful UX, and shipped work in consumer-facing products. Ability to break down complexity and design flows that feel simple, clear, and trustworthy. Experience running user research, prototyping, and testing end to end. Comfort working with engineers and product managers to ship at speed. Bonus: experience in marketplaces, fintech, mobility, or other consumer apps with high complexity. Note: 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 recruiting@jerry.ai 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.
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You could work anywhere. Jerry is building the first AI-powered assistant to make car ownership accessible and affordable for 80% of Americans who rely on it daily — from buy/sell to insurance, financing, safety, maintenance and repairs, we’re reimagining the entire ecosystem. This is a $2T problem and a difficult one to solve. Today, over 5M Americans trust us to take care of their insurance shopping, maintenance and safety, and we’re just getting started. We launched our app in 2019, reached profitability in 2024, and are on track to become a $10B company by 2030. Millions of people rely on Jerry to make buying, owning and maintaining their car easier and more affordable. We want Jerry to feel like a trusted friend in your pocket — someone who handles the hard parts, explains things clearly, and has your back when it matters most. Design is how that vision comes to life. As one of the first designers on the team, your work will directly shape how Jerry looks, feels, and works at scale. You’ll influence not only what we build next, but also our bar for design that will define Jerry for years to come. What You’ll Work On
Drive measurable gains in user engagement and onboarding across Jerry’s core offerings (shop, safety, repairs) by crafting delightful, friction-less experiences. Ship 0→1 features that modernize car care for the everyday car owner. Conduct and synthesize user research (qual + quant), rapidly prototype in Figma, and validate solutions with usability testing and A/B experiments. Raise the UX quality bar across the board: clarity, speed, and consistency. Thoughtfully apply AI to make Jerry faster, clearer, and more helpful. Who You’ll Work With
Art Agrawal (CEO & Head of Product) — your direct manager until we hire our first Head of Design. Patrick Westwood (Founding Designer) who has already taken Jerry from 0 to 5M users. A broader product org of 11 product managers, 55 engineers, and 12 product analysts/data scientists, all driven to build the best-in-class consumer experience. What We’re Looking For
A portfolio that demonstrates strong visual taste, thoughtful UX, and shipped work in consumer-facing products. Ability to break down complexity and design flows that feel simple, clear, and trustworthy. Experience running user research, prototyping, and testing end to end. Comfort working with engineers and product managers to ship at speed. Bonus: experience in marketplaces, fintech, mobility, or other consumer apps with high complexity. Note: 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 recruiting@jerry.ai 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.
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