Jerry is hiring : Staff Product Designer in Chicago

Join Jerry as a Staff Product Designer

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.

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.

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.

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

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