Product Design Lead

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.

To date, Shepherd has raised over $20M from leading investors, including:

• Spark Capital
• Costanoa Ventures
• Y Combinator
• Susa Ventures
• Intact 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.

You enjoy working in a face‑paced environment working closely with leadership on defining product goals and design outcomes. You sweat the details, crafting designs and a product you’re proud to share with the world. You respond to customer feedback, oftentimes challenging our earlier assumptions and hypotheses. You enjoy experimenting with different ideas in search of the best solutions. Finally, you care about customers – especially ones who are not tech native, figuring out ways to break down complex workflows into easy‑to‑use ones.

As our founding designer, you will have a wide product surface area, covering customer facing products, Shepherd’s internal platform, and more.

As our first full time designer, you will work closely with our engineering team and our Cofounder + CTO, Mo, taking their feedback and making fast iterations. We don't expect you to get it right the first time (no one does) but we do expect you to seek out and quickly turn around feedback both from the team and our users.

We aren't a super traditional team, but we are an extremely effective one. We love unique backgrounds, hard workers, and intelligent people who take pride in everything they do. This is a high impact, high visibility role where you will partner closely with teams across Shepherd to evaluate key questions, solve problems, and drive results.

We have offices in San Francisco and New York. We love working together in person and are looking for candidates who can be onsite at our San Francisco HQ.

• Own all of design at Shepherd, shaping our design language, branding, user experience and more
• Create a design process and review process with engineering
• Work closely with the Cofounder/CTO and Head of Product on ideation
• Work closely with customers to understand their needs and design mocks and/or prototypes to collect feedback
• Work closely with engineering to make sure we’re building products that are easy to use and intuitive

• 5+ years of experience, preferably at a SaaS company
• Experience shipping at least one full product or a significant feature as the lead designer
• Experience iterating with engineers and other team members on both visual and UX designs to get the experience and details just right
• Great presentation, collaboration and communication skills
• Fluency in Figma and prototyping tools
• Understanding of the technical limitations and workflow for building web interfaces

• 🏥 Premium Healthcare — 100% contribution to top-tier health, dental, and vision
• 🏖️ 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, or Dallas‑Fort Worth Offices — Premium office spaces on both coasts with daily lunches provided
• 📚 Professional Development — Access to premium coaching, including leadership development
• 🏦 401(k) Plan — Competitive 401(k) plan offered
• 🐶 Dog‑friendly office — Plenty of dogs to play with and make friends with in the SF office

Compensation Range: $200K - $220K