Senior Product Designer, Client Management

Headway is building a new mental healthcare system everyone can access. As a Senior Designer leading our new Client Management pod, you'll own the design of Headway's calendar, scheduling, and messaging experiences. These are 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. Our design team works AI-first. Designers use Claude Code and Cursor to prototype, ideate, and ship improvements to our codebase. We want designers who already work this way and treat AI as a primary part of their practice.

Responsibilities

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.

Requirements

Have 5+ years of product design experience, with real time spent on complex, workflow-heavy product surfaces.; Bring exceptional visual and interaction craft. You 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.; Prototype and test ideas quickly with Claude Code, Cursor, or your AI tool of choice. AI generates the pixels and prototype. You define the patterns, behaviors, and quality bar.; Want your work to make a meaningful difference — these surfaces shape how providers run their practice and how reliably patients get care.; We want designers who already work this way and treat AI as a primary part of their practice.

Benefits

Equity compensation; Medical, Dental, and Vision coverage; HSA / FSA; 401K; Work-from-Home Stipend; Therapy Reimbursement; 16-week parental leave for eligible employees; Carrot Fertility annual reimbursement and membership; 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st; Flexible PTO; Employee Assistance Program (EAP); Training and professional development