Staff Product Designer
Jerry
Why Join 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. Staff Product Designer 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. Equal Employment Opportunity 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
$164k - $246k
...transform the accounting profession. At FloQast, design is a driving force behind our AI-powered... ...operate with clarity and precision. Product design shapes: 1) How complex data... ...available at this time What You'll Do As a Staff Product Designer, you will be a principal...SuggestedWork at officeWorldwide3 days per week$125k - $175k
...The Role This role will help drive the impact of our AI‑enabled care platform designed to help clinicians deliver the next guideline‑based step in a patient’s care journey. As a Staff Product Designer, you will design platform‑level, end‑to‑end workflows that solve complex...Suggested$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 cross-functional teams to drive product strategy and ensure alignment with business goals. The ideal...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...Suggested
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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 with various stakeholders to improve user experiences. The ideal candidate will have...Suggested$180k - $240k
Overview Hi, I'm Chris, head of Product Design at Ashby. We’re looking for a versatile, intrinsically motivated designer eager to contribute to rethinking how modern software is designed. At Ashby, you'll wear multiple hats—designer, product manager, consultant, and design...Work at office- 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 ideal candidate should have over 10 years of experience and a strong portfolio showcasing expertise...Flexible hours
$150k - $190k
...destiny. How do we do it? We provide cutting-edge products and services that enhance the trading... ...world. What you'll do: NinjaTrader’s growing Design organization is seeking an experienced, highly skilled, and creative Staff UX Product Designer. Your passion for simplicity...Work at officeRemote workWorldwideMonday to FridayFlexible hours- 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 involves defining design approaches for complex challenges, facilitating collaboration across teams...Flexible hours
- 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...
$164k - $246k
...accounting profession. At FloQast, design is a driving force behind our AI-powered... ...teams operate with clarity and precision. Product design shapes: 1) How complex data becomes... ...at this time What You'll Do: As a Staff Product Designer - Platform/Design...Work at officeWorldwide3 days per week- 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
$60k - $70k
...Applicants must be legally authorized to work in the United States on a permanent basis without requiring employer sponsorship. Staff Designer As the embodiment of design thinking, you bring ideas to life, extending visual language into functional mediums. You turn...Permanent employmentCasual workFlexible hours- ...native development changed engineering first, but it's changing design just as fast. The line between a Figma file and a shipped... ...collapsing - and we want designers who are already shipping on the production side of that line. If you've used AI prototyping tools to ship...Work at office
$90k - $110k
...solutions that close data and process gaps, connect stakeholders, and accelerate job placement and prosperity at scale. Overview The Product Designer plays an essential role in the creation and continuous improvement of STEAMe products. You'll own end‑to‑end user experiences—...Work at officeWork from home$60k - $70k
Vsapartners in Chicago is seeking a Staff Designer to assist in creating visual designs and brainstorming creative concepts. This role requires a strong background in design, collaboration skills, and the ability to integrate ideas across various mediums, including print...- ...In this role, you will start by taking ownership of specific product surfaces. As you demonstrate your ability to master complexity,... ...driven iteration to translate raw user pain points into actionable design improvements Your work will also help scale our design system,...Full timeWork at officeRemote workFlexible hours
$126k
...industry‑leading signage solutions. We are looking for an experienced digital designer to join our creative team and help deliver engaging customer experiences. Responsibilities Develop product design concepts from complex sets of requirements. Produce high‑quality...Flexible hours- ...allowing you to work remotely or from their offices in San Francisco or Toronto. The Opportunity Juniper Square is seeking a Product Designer to join their GPX product team. You’ll focus on designing user experiences for both investment managers and their investors. This...Remote workFlexible hours
- ...Keeper Security is hiring a talented creative and visionary Senior Product Designer to join our passionate team in shaping the next generation of our products and services. The position is 100% remote from select locations and offers a hybrid schedule for candidates near...Temporary workRemote workWorldwide
- 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 Interaction, UX Design, or related fields, with at least one year of digital design experience....Remote jobHourly payWork from homeFlexible hours$78k - $98k
## Senior UX Product DesignerApplylocations: Canada-Toronto, ON-Office: Chicago, IL: Denver, COtime type: Full timeposted on: Posted Yesterdayjob... ....**Why this Role Matters**As a **Senior** **UX** **Product Designer** at Litera, you will play a critical role in shaping intuitive...Work at officeWorldwide3 days per week$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...- Tempus, Inc. in Chicago is looking for a Staff Product Designer to influence design strategies in healthcare technology. You will collaborate with various teams to develop AI-enabled workflows, ensuring they meet user needs and business objectives. This role requires strong...
- Scholarship Solutions, LLC is seeking a product designer based in Chicago to join our AI-native product team. In this role, you will ship UX, UI, and interaction work directly into production, collaborating closely with engineering and product teams. We value innovation...Work at office
$75k - $80k
tms in Chicago is seeking a creative Product Designer to develop fun and marketable products for kids and teens. The ideal candidate will have a degree in Toy or Product Design and 3+ years of relevant design experience. Responsibilities include generating innovative product...- ...Full-time About The Role Hi, I’m JC, Head of Design at Zen Educate. I started sketching out the first versions of our product on evenings and weekends — before we had a team... ...look like: Speaking to educators or school staff to understand a problem in depth Synthesising...Full timeTemporary workCasual workWork at officeLocal areaImmediate startWeekend workAfternoon shift3 days per week
- Quantifind is looking for a UI/UX Designer based in Chicago, Illinois, to take ownership of product surfaces. You will collaborate closely with Product Management and Engineering while driving features from research to high-fidelity specifications. The ideal candidate will...Remote jobFlexible hours
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