You could work anywhere. Why join Jerry?

Jerry is building the first AI-powered assistant for car ownership, making it easy and affordable for the 80% of Americans who rely on their cars every day. From buying and insurance to financing, safety, and repairs, we’re reimagining the entire experience of owning a car.

It’s a $2T industry that’s fragmented, analog, and full of friction — and no one else is tackling it end-to-end. Since launching in 2019, over 5 million people have trusted Jerry to manage their car insurance, maintenance, and safety. We reached profitability in 2024, are backed by $240M in funding, and are on track to become a $10B company by 2030.

Customers love what we’ve built, and we’re just getting started. Now we’re ready to elevate our craft, define our brand, and design the next generation of products that make car ownership feel effortless. In other words: we have function. Now we need form.

Why this role matters

Design is how we make car ownership feel easy… and even enjoyable.

As a Senior Product Designer, you’ll play a key role in shaping how millions of people interact with Jerry’s core products. You’ll collaborate closely with PMs, engineers, and data scientists to translate complex problems and data into clear, intuitive, and visually polished experiences.

You’ll own end-to-end design. From mapping user flows and crafting wireframes to refining high-fidelity visuals, and using prototypes to bring ideas to life. Your work will help drivers make better decisions about insurance, safety, and repairs with confidence and ease.

What you’ll work on

• Partner with PMs and engineers to define user problems, simplify data-heavy experiences, and design solutions that drive measurable outcomes.

• Create user flows, low- and high-fidelity wireframes, prototypes, and final UI for features across Jerry’s core products.

• Lead UX explorations for complex problems — structuring workflows that make car ownership and management feel simple and intuitive.

• Leverage research, analytics, and experimentation to inform design decisions and validate your approach.

• Collaborate with other designers to evolve our design system and raise our craft bar across mobile and web.

• Thoughtfully apply AI to improve clarity, personalization, and automation in the experience.

Who you’ll work with

You won’t be another cog in a big design machine. You’ll collaborate directly with:

• Kruise Sapstein – Head of Design, leading Jerry’s product design vision and building a high-performing, high-craft design culture.

• Art Agrawal – CEO & Head of Product, shaping company direction and customer experience at the highest level.

• A broader product org of 11 PMs, 55 engineers, and 12 analysts/data scientists, all driven (🚗) to build a best-in-class consumer experience.

What we’re looking for

• A portfolio that showcases strong UX thinking, data-informed decision making, and clean, intuitive interface design.

• 5+ years of experience designing consumer-facing mobile or web products (agency or in-house).

• Proven ability to translate complex data and product requirements into simple, elegant workflows.

• Comfortable collaborating with PMs and engineers to define scope, prioritize solutions, and iterate quickly.

• Skilled in Figma and experienced with rapid prototyping tools to communicate ideas clearly.

• Understanding of design systems and how to use or evolve them for consistency and scale.

• Excellent communication skills — able to articulate design rationale clearly to technical and non-technical partners.

Bonus: experience in marketplaces, fintech, insurance, or mobility.

While we appreciate your interest and application, due to the volume of applications we receive, only applicants under consideration will be contacted.

Please note: Jerry.ai is only able to hire employees who currently reside in AZ, CA, CO, FL, GA, IL, MA, NC, NJ, NV, NY, OR, TN, TX, UT, VA, or Ontario, Canada. We cannot accept applications from candidates residing elsewhere at this time.

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

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.