Staff Product Designer — AI‑Powered Car Care Experience
Jerry
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 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, only applicants under consideration will be contacted. 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 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. #J-18808-Ljbffr Jerry
$125k - $175k
Tempus AI is seeking a Staff Product Designer in Chicago, IL, to enhance its AI-enabled care platform. This role involves designing complex workflows and collaborating with... ...The ideal candidate brings over 8 years of experience in fast-paced environments, exceptional product...Suggested$125k - $175k
Tempus AI, Inc. is seeking a Staff Product Designer to influence the impact of our AI-enabled care platform. Your role will involve designing platform-level workflows and collaborating... ...various stakeholders to improve user experiences. The ideal candidate will have 8+ years...Suggested- Epsilon is seeking a Senior Staff Product Designer in Chicago to lead the design of user-centered experiences across global advertising and marketing technology platforms. The... ...defining design approaches, leveraging AI for ideation and validation, and establishing...SuggestedFlexible hours
$164k - $246k
...industry, providing an AI-powered Accounting... ...profession. At FloQast, design is a driving force behind... ...clarity and precision. Product design shapes: 1) How... ...time What You'll Do As a Staff Product Designer, you... ...high-trust, and scalable experiences that remove adoption barriers...SuggestedWork at officeWorldwide3 days per week$125k - $175k
...Staff Product Designer Passionate about precision medicine and advancing the healthcare... ...have finally made it possible for AI to impact clinical care in a meaningful way. Tempus' proprietary... ...Approximately 8+ years of experience in fast-paced creative environments...Suggested- Epsilon is seeking a Senior Staff Product Designer to drive innovative, user-centered experiences across its global advertising and marketing platforms. This role involves defining design strategies for complex challenges, working autonomously to deliver solutions that...
- A leading accounting technology firm in Chicago is looking for a Staff Product Designer to define design strategy, enhance AI capabilities, and elevate user experience for its platform. Ideal candidates should have 7+ years of experience in SaaS product design, demonstrate...
- Publicis Groupe Holdings B.V is seeking a Senior Staff Product Designer in Wakefield, MA to drive design for user-centered experiences across Epsilon's platforms. This role... ...modern design sensibilities with a focus on AI-driven methodologies. The ideal candidate will...Flexible hours
$164k - $246k
...industry, providing an AI-powered Accounting... ...profession. At FloQast, design is a driving force behind... ...clarity and precision. Product design shapes: 1) How... ...system and platform-level experiences, driving quality,... ...What You'll Do: As a Staff Product Designer -...Work at officeWorldwide3 days per week$130k - $190k
Product Engineer High level stuff you... ...I picked up an AI teacher qualification... ...out our own AI powered knowledge‑base... ...Managers and Designers are partners... ...career path. We care more about impact... ..., Senior, or Staff here. Instead,... ...clear direction, experience of different...Remote jobFull timeTemporary workWork at officeLocal areaImmediate startMonday to Friday$90k - $110k
...nationally recognized social care referral platform that... ...-sided platforms that power complex ecosystems. We... .... Overview The Product Designer plays an essential... ...own end-to-end user experiences — from user research through... ...requirements Use AI-powered design and...Work at officeWork from home$78k - $98k
## Senior UX Product DesignerApplylocations: Canada-Toronto... ...what’s possible through AI, innovation, and solutions that power millions of legal professionals... ...** **UX** **Product Designer** at Litera, you will... ...into clear, user-centered experiences. Partnering closely with...Work at officeWorldwide3 days per week- Kake is seeking a Product Designer to lead design on client projects, focusing on digital experiences, including AI-powered products. The right candidate will own the design process, from navigation and layout to final release, ensuring functional and visually appealing...Remote job
- Hi! I'm Chris, head of Product Design at Ashby. We're looking for a versatile... ...and Benji (our founders) care deeply about design, which... ..., and provides an excellent experience for the candidate. To... ...teams with intelligent and powerful software that provides insights...Full timeWork at officeRemote work
- ...based healthcare voice AI company building an... ...patients. About the Design Team You’ll join as the Product Designer , working... ...ll help shape how AI-powered enterprise... ...Designer with 3 years of experience who is excited to design... ...genuine understanding and care for patients,...Work at officeLocal area3 days per week
$27 - $42 per hour
...you for who you are, care for your well-being,... ...ideas, such as AI-enabled insights and technology-powered solutions, to enhance... ...professional In addition, staff may have diverse... ...a broader range of experiences earlier in their careers... ...and/or Sunday) Car may be required to travel...CarHourly payFull timeWork experience placementSummer workInternshipLocal areaWorldwideWeekend workAfternoon shift$150k - $190k
...it? We provide cutting-edge products and services that enhance the... ...ll do: NinjaTrader’s growing Design organization is seeking an experienced... ...highly skilled, and creative Staff UX Product Designer. Your... ...deliver best-in-class user experiences, and you will drive both the...Work at officeRemote workWorldwideMonday to FridayFlexible hours- A leading trading platform company is seeking a Staff UX Product Designer in Chicago, IL. The role involves enhancing customer experiences, collaborating with cross-functional teams, and driving innovation in design solutions. Candidates should have a strong portfolio,...Remote work
$115k - $135k
...strong foundation in UI/UX design, you bring a true product mindset to your work. You... ...constructive feedback as a powerful tool for improvement and... ...experts. Additionally, you see AI as a true partner in the... ...years of professional experience in UI/UX design A bachelor...CarFull timeWork at officeFlexible hours$200 per day
...Time. Family Company. We Care. Hiring AreaFor... ...2018 and 2020 Cummins-powered International Pro Stars... ...mile—keeping your road experience worry-free.Competitive... ...NO BALLOON Payment!The Car GiveawayBack by popular... ...our recruiting campaigns designed to attract and hire new...CarWeekly payFlexible hours$120k - $150k
...About Hopscotch Primary Care At Hopscotch Primary Care... ...you want to bring your experience, skill and passion to... ...We are looking for a Product Engineer, Care Delivery to help design and build the next generation... ...of operational and AI-powered tools that support care...Temporary workLive inShift work- Litera Group is seeking a Senior UX Product Designer for a hybrid role based in Chicago, IL. This position is crucial for shaping user-centered experiences to empower legal professionals. You will manage the design processes, influencing product direction through collaboration...
$50 per hour
Prolific is seeking Product Designers and UX Specialists in Chicago, Illinois, to train and evaluate AI models. This role requires a Bachelor's/Master's/PhD in Human-Computer... ..., with at least one year of digital design experience. You'll assess AI-generated designs for...Remote jobHourly payWork from homeFlexible hours- ...experienced Desktop/Workstation Design Engineer to participate in... ...for this position will possess experience with integrating and upgrading... ...relations for years to come. We care about our employees. Therefore... ...use artificial intelligence (AI) tools to support parts of the...Full timeWork at officeRemote workFlexible hours
- Tempus, Inc. in Chicago is looking for a Staff Product Designer to influence design strategies in... ...collaborate with various teams to develop AI-enabled workflows, ensuring they meet... .... We seek someone with 8+ years of experience and a compelling portfolio to demonstrate...
$140k - $155k
DesignX Community, a fast-growing SaaS company in Chicago, is seeking a Senior Product Designer. This role requires deep experience in designing software products end-to-end, from problem definition to implementation. Join a passionate team that values autonomy and team...$90k - $110k
STEAMe LLC, located in Chicago, is looking for a Product Designer to enhance user experiences across their products. This hybrid position requires collaboration with product managers and engineers to create compelling solutions that drive social impact. Candidates should...- Senior Product Designer (Brand + Growth Experience) About NOCD NOCD is the #1 telehealth provider for the treatment of obsessive‑compulsive disorder (OCD... ...clinically proven OCD treatment, by removing barriers to OCD care, and reducing the stigma associated with OCD. We’re...Full timeFreelanceWork at office
- Agoda is seeking a Product Designer to join the Customer Experience Group (CEG) team in Chicago. This role focuses on driving UX while aligning with business goals, enhancing booking-related inquiries and ensuring customer satisfaction. The ideal candidate will have over...
- ...healthcare technology company based in Chicago seeks a skilled Product Designer with 3 years of experience in designing complex, data-driven enterprise software.... ...should be proficient in using tools like Figma and AI technologies to create intuitive user experiences. The...Work at office3 days per week
Do you want to receive more vacancies?
Subscribe and receive similar vacancies to Staff Product Designer — AI‑Powered Car Care Experience. Be the first to apply!
- assistant designer Chicago, IL
- staff product designer Chicago, IL
- product designer ux ui Chicago, IL
- product designer remote Chicago, IL
- product designer senior Chicago, IL
- product designer Chicago, IL
- auto delivery driver Chicago, IL
- car wrap Chicago, IL
- car dealership part time Chicago, IL
- auto sales manager Chicago, IL


