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 recruiting@jerry.ai 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.

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, 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 recruiting@jerry.ai 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.

• Develop creative, customer-centric, performance-based training materials. • Manage learning product development projects, including scoping, managing Subject Matter Experts (SMEs), and working with other departments. • Work with our Customer Excellence teams and SMEs to create storyboards/scripts and production-ready content that meet employees' needs. • Report on and communicate the results of educational content to cross-functional stakeholders. • Stay current on new learning approaches, behavioral science, and technology, and apply that knowledge to our learning products. • Become a Smartsheet product expert • Be an Administrator for the Learning Management System (LMS). Maintain systems, create user profiles, create usage reports, publish SCORM, video, and other digital content etc. • Other job duties as assigned.

• Lead end-to-end design for a product area- from discovery and concept to delivery and iteration. • Work in product trios (Product, Engineering, Design) to define problems, validate opportunities, and shape product strategy. • Modernize legacy platform experiences by simplifying complex workflows and designing scalable, modular solutions. • Use data, user research, and business insights to prioritize impact and ensure alignment with company strategy. • Partner with engineers to ensure high-quality implementation and advocate for design excellence in execution. • Contribute to and evolve our design system, ensuring consistency and usability across the platform. • Mentor junior designers and contribute to team rituals and design culture.