Staff Product Designer

Staff Product Designer

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 a Staff Product Designer, you'll help shape how Jerry looks, feels, and works. Defining what great design means at scale. You'll lead design initiatives from 0 →1, elevate design quality across products, and influence how we tell our story through craft and clarity. Your work will directly shape the experience for millions of users and set the standard for years to come.

What You'll Work On

• Lead design for key products across Jerry's core offerings — insurance, safety, repairs, and beyond.
• Ship 0→1 features that modernize car care for everyday drivers.
• Partner with research, product, and data to identify opportunities and turn insights into impactful design.
• Create elegant, frictionless experiences that drive measurable gains in engagement and retention.
• Build and evolve Jerry's design system to ensure consistency, scalability, and visual excellence.
• Thoughtfully apply AI to make our experience faster, clearer, and more personal.
• Raise the bar for UX and visual design in the form of clarity, speed, and craft.

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 demonstrates exceptional visual design, thoughtful UX, and shipped consumer products at scale.
• 12+ years of product design experience (agency or in-house), ideally across mobile and web.
• Proven ability to own projects end-to-end — from research and concept to launch and iteration.
• Experience building and evolving design systems in collaboration with engineering.
• Comfort working in fast-paced environments and shipping quality work quickly.
• Excellent communication and storytelling skills to align cross-functional teams.

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

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 View email address on click.appcast.io.

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.