Senior Product Designer, Client Management

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that. But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens. We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better. About Provider Experience At Headway: Providers run their entire practice on Headway — and the tools they use every day shape both the quality of care patients receive and providers' ability to sustainably run their practice. Some of the biggest administrative burdens in a provider's week comes from managing their calendar, staying on top of messages, and coordinating scheduling with their clients. About This Role: As a Senior Designer leading our new Client Management pod, you'll own the design of Headway's calendar, scheduling, and messaging experiences — the surfaces thousands of providers touch every day. You'll bring systems-minded craft to complex, state-heavy problems (availability, booking and reschedule, timezones, notifications, provider–patient messaging) and keep it all coherent with how providers manage their clients. Your work helps providers spend less time on logistics and more time on care — and keeps availability accurate so patients can book. We're building an AI-first design team at Headway. Designers are expected to use AI tools like Claude, Cursor, and MagicPatterns to prototype and stay involved through launch and iteration directly in code. We're looking for designers who already work this way and see AI as a primary part of their workflow.

Calendar & scheduling. Availability, booking and reschedule flows, Google Calendar OAuth, and getting the hard states right (timezones, conflicts, edge cases). Messaging. Provider–patient messaging, attachments, and the notification/reminder system around it. EHR-craft papercuts. Systematically identify and fix the highest-value usability issues providers have flagged across these surfaces. Coherence with client management. Keep scheduling and messaging consistent with how providers manage their client list and profiles, in partnership with Product. Research & craft. Talk to providers with the research team's support; raise the craft bar and contribute scheduling/messaging patterns to the Helix design system. You'll Be a Great Fit If You: Have 5+ years of product design experience, with real time spent on complex, workflow-heavy product surfaces. Bring exceptional visual and interaction craft — and sweat the edge cases and states that make workflow surfaces trustworthy. Are a systems thinker who can take a messy, multi-state problem and shape it into a coherent experience. Are data-informed — you use qualitative and quantitative insight together to drive decisions. Are a strong cross-functional partner who builds alignment and drives momentum with PM, Eng, and Data. Are comfortable with AI prototyping tools (Claude Code, Cursor, MagicPatterns) and see them as core to how you work. Want your work to make a meaningful difference — these surfaces shape how providers run their practice and how reliably patients get care. Compensation &