Product Design

The Role

We're looking for a great designer — someone who is genuinely cracked at their craft and excited to apply it to one of the most complex product surfaces in fintech.

Shepherd's platform spans underwriting workspaces, AI automation tooling, submission pipelines, broker portals, and pricing interfaces. The problems here are legitimately hard: dense information architecture, real-time AI outputs, high-stakes decisions, expert users. This is the kind of surface that separates designers who are good at making things look clean from designers who can make complex things feel simple.

You're AI-native — not as a buzzword, but as a working practice. You use AI to move faster, explore more, and get closer to the real thing earlier. And you're comfortable going beyond Figma when it serves the work — whether that's writing a quick prototype, editing component code, or sitting in a PR to understand how your design actually lands.

What You'll Do

• Own design for meaningful product areas — how underwriters price risk, how brokers submit and track placements, how AI surfaces recommendations across the platform. These are complex, expert-facing tools where every design decision has real consequences.

• Talk to underwriters, brokers, and ops. Understand the domain well enough to form strong opinions about what good looks like, and bring that clarity into your work.

• Design for AI transparency and trust. A growing share of our platform involves AI making recommendations, extracting data, and taking automated actions. Design the patterns that make that feel reliable and legible — not magic, not noisy.

• Move fast with high craft. Use AI tools to accelerate research, exploration, and iteration. Ship things that are actually good — not just done.

• Work closely with engineers, not just alongside them. Hand off with the kind of detail that reduces back-and-forth. When it helps, write code — edit a component, prototype a flow, inspect a PR. The closer you are to the implementation, the better your designs get.

• Contribute to the design system. Build components and patterns that scale. Raise the quality floor for every surface, not just the ones you're directly working on.

What You Bring

• 3+ years of product design experience at a tech company or startup

• A portfolio showing end-to-end work on complex, data-heavy products

• Strong visual and interaction design fundamentals — hierarchy, purposeful motion, making dense information readable

• An AI-native workflow: you use tools like Claude, Cursor, or v0 as regular parts of how you design and prototype

• Comfort going beyond Figma — writing or editing code, building working prototypes, understanding how your designs get implemented

• A bias toward depth: you ask good questions, form strong opinions, and can articulate the reasoning behind your decisions

• Strong communication and a collaborative instinct, especially across design and engineering

Bonus if you have experience designing for insurance, fintech, or other complex B2B domains, or prior work on AI-heavy surfaces where transparency and trust are core UX challenges.

Why Shepherd

You'll work on a product that is genuinely hard to design — expert users, high-stakes decisions, AI in the loop. The team is small, which means your work has real visibility and real impact. You'll have direct relationships with engineers, PMs, and leadership, and you'll see the effects of your decisions quickly. Commercial insurance is moving.

Some of the things you'll help design