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.

What You'll Own:

• 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 & Benefits:

The expected base pay range for this position is $180,000 - $225,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:
  
  • 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