Design Engineer

Design Engineer WHAT WE DO Shepherd is a technology-driven Managing General Underwriter (MGU) transforming commercial Property & Casualty insurance for high-hazard industries. Our mission is to make risk frictionless for the builders and operators shaping the physical world — protecting progress from concept through construction and into decades of operation. We’re building the fastest, smartest commercial risk platform, where underwriting expertise, data, and automation work together to deliver: - Faster decisions - Smarter, more accurate pricing - Better risk outcomes With Shepherd, safety, speed, and quality no longer trade off against one another — they compound. We’re not just modernizing insurance products. We’re building the risk infrastructure for the next generation of financial services, where technology, underwriting, and partnerships operate in harmony to support the world’s most important industries — and the progress they make possible. OUR INVESTORS To date, Shepherd has raised over $20M from leading investors, including: - Spark Capital https://www.sparkcapital.com/ - Costanoa Ventures https://costanoa.vc/ - Y Combinator https://www.ycombinator.com/ - Susa Ventures https://www.susaventures.com/ - Intact Ventures https://www.intactfc.com/about-us/intact-ventures - And several others OUR TEAM We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About https://www.shepherdinsurance.com/about page to learn more. THE ROLE Design at Shepherd lives at the intersection of craft and code. This isn't a role where design ends at a Figma handoff. You'll own product surfaces end to end — from concept through production — and prototype directly in React and TypeScript before a single ticket is written. We work AI-first. That means using AI tools like Cursor and Claude Code to explore, scaffold, and build earlier in the process — with Figma coming in for systems and polish. We're looking for a Design Engineer who thinks like a product designer, ships like a front-end engineer, and treats AI as a genuine collaborator. What You'll Do - Own product surfaces end to end — underwriting workspaces, submission ingestion, AI recommendation surfaces, broker-facing portals. Use layout, motion, and interaction to make complex insurance workflows feel obvious. - Prototype in code and validate fast. Build working prototypes in React and TypeScript, test them with real users — underwriters, brokers, our ops team — before you systemize anything. - Work AI-first with Cursor and Claude Code. Use them as your starting point for drafting intent, scaffolding components, and exploring implementations. Apply your own judgment to close the gap between "good enough" and great. - Bridge design systems, product, and engineering. Translate Shepherd's design principles into reusable components and patterns so the team can move faster without sacrificing craft. - Design for AI transparency. Our underwriting automation surfaces recommendations, extracts data, and takes actions on behalf of users. Design the patterns that make that legible — showing what the AI did, why, and what comes next — without overwhelming the interface. - Champion accessibility and performance. Semantic HTML, focus states, reduced motion, Core Web Vitals. These aren't afterthoughts; they're part of the bar. - Share what you're learning. Document the prompts, patterns, and workflows you've developed. Help raise the floor across the team. What You Bring - Strong ownership across both design and front-end engineering, from idea to shipped interface - Fluency in Figma, React, TypeScript, semantic HTML, and modern CSS - Active use of tools like Cursor and Claude Code, with real opinions on how to get quality output - A portfolio showing high visual and interaction craft in live products or working prototypes - A systems mindset — you think in components and patterns, not one-off screens - Care for acces ... (truncated, view full listing at source)