Staff Product Designer

19 hours ago

Toronto, Canada Jerry Full time

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 (

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