Jerry
2 days ago — Be among the first 25 applicants
Why join Jerry? Jerry is building the first AI‑powered assistant for car ownership, making it easy and affordable for 80% of Americans who rely on cars daily. From buying and insurance to financing, safety, and repairs, we’re reimagining the entire ownership experience. It’s a $2 trillion 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 for insurance, maintenance, and safety. We reached profitability in 2024, have $240 M in funding, and are on track to become a $10 B company by 2030.
Why this role matters Design is how we make car ownership feel easy and even enjoyable. As a
Senior Product Designer , 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 user flows and wireframes to high‑fidelity visuals and prototypes, helping 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
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.
Equal Employment Opportunity Statement 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.
Compensation and Benefits 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. 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.
Seniority level Mid‑Senior level
Employment type Full‑time
Job function Design, Art/Creative, and Information Technology
Industries Software Development
Referrals increase your chances of interviewing at Jerry by 2x
Locations and Salary Chicago, IL $90,000.00-$99,000.00 3 days ago
Oak Brook, IL $68,000.00-$77,000.00 1 week ago
Chicago, IL $150,000.00-$180,000.00 1 week ago
Chicago, IL $150,000.00-$180,000.00 1 week ago
Senior Product Designer - Health and Wellness
Oak Brook, IL $106,000.00-$130,000.00 1 week ago
Chicago, IL $150,000.00-$180,000.00 1 week ago
Chicago, IL $150,000.00-$180,000.00 1 week ago
Volunteer: Give career advice to a future User Interface (Ui) Designer
We’re unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI.
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Why join Jerry? Jerry is building the first AI‑powered assistant for car ownership, making it easy and affordable for 80% of Americans who rely on cars daily. From buying and insurance to financing, safety, and repairs, we’re reimagining the entire ownership experience. It’s a $2 trillion 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 for insurance, maintenance, and safety. We reached profitability in 2024, have $240 M in funding, and are on track to become a $10 B company by 2030.
Why this role matters Design is how we make car ownership feel easy and even enjoyable. As a
Senior Product Designer , 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 user flows and wireframes to high‑fidelity visuals and prototypes, helping 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
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.
Equal Employment Opportunity Statement 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.
Compensation and Benefits 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. 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.
Seniority level Mid‑Senior level
Employment type Full‑time
Job function Design, Art/Creative, and Information Technology
Industries Software Development
Referrals increase your chances of interviewing at Jerry by 2x
Locations and Salary Chicago, IL $90,000.00-$99,000.00 3 days ago
Oak Brook, IL $68,000.00-$77,000.00 1 week ago
Chicago, IL $150,000.00-$180,000.00 1 week ago
Chicago, IL $150,000.00-$180,000.00 1 week ago
Senior Product Designer - Health and Wellness
Oak Brook, IL $106,000.00-$130,000.00 1 week ago
Chicago, IL $150,000.00-$180,000.00 1 week ago
Chicago, IL $150,000.00-$180,000.00 1 week ago
Volunteer: Give career advice to a future User Interface (Ui) Designer
We’re unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI.
#J-18808-Ljbffr