Staff Product Designer

Because your car is the single (or second) most expensive thing you’ll ever own, and the hardest and most painful to manage. 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 (car services are verticalized, service providers are analog, etc), and no one else is tackling it end to end. 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.

Customers like our

app

(although we think it could be 10X better), we’re well capitalized, and now we’re ready to shape our brand and story, level up our craft, and build our next phase of products. In other words, we have function, now we need form.

Seniority level : Mid‑Senior level

Employment type : Full‑time

Job function :

Design, Art / Creative, and Information Technology

Industry : Software Development

Why This Role Matters

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

You won’t be another cog in a big design machine. You’ll work closely 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.

While we appreciate your interest and application, only applicants under consideration will be contacted.

Equal Employment Opportunity

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 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.

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.

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