Design Engineer

Shepherd is an AI-native commercial insurance platform transforming how high-hazard industries get covered. 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.

The infrastructure behind the AI boom — data centers, semiconductor fabs, renewable energy assets — has to be built and insured. But traditional carriers weren't built for this speed:

• Complex commercial construction projects routinely wait weeks for a single quote

• Legacy carriers rely on static applications and disconnected systems

• Brokers chase carriers through calls, emails, and resubmissions

We built Shepherd to solve that. Our AI performs the same underwriting workflows in seconds, and integrates real-time data from construction technology partners — Procore, Autodesk, OpenSpace, DroneDeploy, and others — to see risk as it actually exists, not just as it was reported on a static form.

We're pursuing the most ambitious technical vision in commercial insurance: fully autonomous underwriting. We're closing in on the first fully agentic submission in the industry — email in, price out, no human intervention until the last mile.

With Shepherd, safety, speed, and quality no longer trade off against one another — they compound. We're building:

• Faster decisions

• Smarter, more accurate pricing

• Better risk outcomes for insureds who invest in safer practices

We're not just modernizing insurance products. We're building the risk infrastructure for the next generation of financial services.

In March 2026, Shepherd raised a $42M Series B — bringing total funding to over $60M — led by Intact Private Capital, the investment arm of one of the largest insurers in the world. Intact is not only our lead investor but also a carrier partner, a testament to the confidence the incumbent industry has in what we're building. Our investors:

• Intact Private Capital

• Spark Capital

• Costanoa Ventures

• Y Combinator

• Susa Ventures

• And several others

We're a team of technologists and insurance enthusiasts, bridging the two worlds together. Check out our About page to learn more.

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 accessibility and performance as core parts of craft, not compliance checkboxes

• Clear communication and comfort pairing across design, engineering, and product

Bonus if you have experience contributing to a design system or component library, familiarity with experimentation or analytics tooling, or prior work on complex B2B workflows, fintech, or insurance.

Why Shepherd

We're a small team solving a genuinely hard problem with real stakes. Commercial insurance is a trillion-dollar market that's been underserved by technology for decades. The work here has density — every surface you design is used by people making real underwriting decisions, and you'll see the impact quickly. You'll have a direct line to leadership, real ownership over what you build, and a team that cares deeply about craft.

Some of the things you'll be designing

🏥 Premium Healthcare
100% contribution to top-tier health, dental, and vision

🥕 Fertility benefits and family building support

🏖️ Unlimited PTO
Flexibility to take the time off, recharge, and perform

🥗 Daily lunches, dinners, and snacks
We work together, and enjoy meals together too

🖥️ SF, NYC, Dallas-Fort Worth, Chicago and LA Offices

📚 Professional Development
Access to premium coaching, including leadership development

🏦 Competitive 401(k) Plan

🐶 Dog-friendly office
Plenty of dogs to play with and make friends with in the SF office