Product Design Lead

About Goodbill

About the role

You will:

• Own product design end-to-end. From discovery and customer conversations through wireframes, prototypes, high-fidelity mocks, and production. You're responsible for the full arc. You'll talk to customers daily: joining sales calls, customer syncs, running user research, sitting in on support tickets, whatever it takes to build the right thing.
• Build the design system. Take our nascent Figma component library and turn it into a real system that is consistent, scalable, and opinionated enough to accelerate engineering throughput dramatically.
• Design for AI-native experiences. Rethink traditional healthcare workflows through the lens of what AI makes possible. You're not adding AI to existing patterns; you're designing new patterns that couldn't exist without it.
• Ship to production. Use AI-assisted development tools (we use Devin, but you're welcome to use Claude Code, Cursor, Codex, or whatever you prefer) to take your designs from Figma to deployed code, even if incrementally. You'll be empowered and expected to close the gap between design and production yourself.
• Shape brand and positioning. Goodbill's visual identity is always evolving. You'll have a strong voice in where it goes, always ensuring we present a sharper, more intentional expression of who we are and where we're headed.
• Partner deeply with engineering, operations, and leadership. You'll report to our CTO and work closely with our CEO. You'll design alongside 3–4 engineers in a team that moves extremely fast. Your designs need to be clear enough to build from immediately and flexible enough to evolve as we learn.

You are:

• A systems thinker who sweats the pixels. You can hold the entire product in your head while obsessing over a 2px alignment issue. You see how a component decision cascades across five surfaces and you care about all of them.
• Ruthless about killing your darlings. You don't get emotionally attached to your work. You get attached to outcomes. If a better solution emerges, from a customer conversation, an engineer's suggestion, or your own second look, you move to it without ego.
• AI-fluent. You use AI tools daily for prototyping, production, and pixel-perfection. You understand what agentic AI products feel like and you design for them natively, not as an afterthought.
• Fast and decisive. You thrive in environments where speed matters. You know when a rough wireframe is the right artifact and when a polished prototype is worth the time. You default to shipping over perfecting.
• Customer-obsessed. You're not designing from your desk. You're on calls, reading tickets, watching sessions. You build empathy through direct contact, not assumptions.
• Comfortable with complexity. Healthcare is messy: regulatory requirements, EDI standards, insurance jargon, and emotionally-charged moments for patients. You're energized by the challenge of making all of that disappear behind a clean interface.
• A strong communicator. You can articulate design rationale to engineers, executives, and customers with equal clarity. You bring people along without slowing down.
• Collaborative. You’ll work closely with Product, Operations, Sales, and Client Success to design features that move real dollars in the healthcare system.

Bonus

• Experience designing in healthcare, fintech, or other regulated domains.
• Familiarity with healthcare billing, claims processing, or insurance administration.
• You've built or contributed to a design system from the ground up.
• You’ve worked in an early-stage startup (pre-seed/seed/Series A).
• You've shipped code to production using AI-assisted design and development tools.

Why Goodbill

• Massive problem, huge upside. Americans and employers spend nearly half a trillion dollars a year on hospital care — much of it wasted. We’re fixing that with AI and software.
• Recognition + traction. Named one of TIME’s Best Inventions of 2023; serving 5,000+ employers and 250,000 patients; backed by top VCs (Eniac, Maveron, Founders’ Co-op, Reach Capital, Liquid2).
• Rare design range. You'll design enterprise admin tools and consumer experiences in the same week, possibly the same day. Few roles offer this breadth at this stage.
• Ground-floor impact. You're building the design function. Your decisions on systems, patterns, and brand will define Goodbill's product for years.
• Mission-driven team. We live our values: do it for the patient, lead without ego, be transparent, own it, move quickly, sweat the details.

We offer

• Competitive pay (cash and equity)
• Unlimited PTO (Seriously — it’s not an empty benefit. We work too hard for anything else.)
• Health, dental, and vision plans covered 100% for you and 50% for dependents
• A monthly fitness stipend
• Internet or co-working space stipend
• Primary care membership stipend
• Remote office equipment stipend
• Quarterly team retreats