Senior Headway Jobs (NOW HIRING)

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. 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.
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. 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.

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

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem - across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.
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A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.