Design Director, Provider Experience

About the Role:

Headway's EHR is the daily operating system for tens of thousands of mental health providers — where they schedule sessions, document care, manage clients, and run their practice. This role owns the design vision and execution for that experience, with the goal of making Headway the practice partner that providers choose to build their entire practice on.

This is a complex, high-stakes design challenge. A single session on Headway touches scheduling, telehealth, clinical documentation, outcome measurement, insurance verification, and billing. Today, we're reimagining these workflows with AI at the center: transcript-powered session notes, AI-enabled scheduling, co-pilot features, etc.

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 a design leader who's already working this way and can raise the bar for the entire team.

In This Role, You Will:

• Drive the provider EHR experience strategy and vision — partner with product, engineering, and senior leadership to define what an AI-native practice management experience looks like across scheduling, documentation, session experience, and client engagement.
• Hire, attract, and manage a team of designers. Set a high craft bar that inspires senior designers, and coach the team to consistently make strong experience and quality tradeoffs.
• Own strategic design initiatives hands-on as a player-coach, lead the design of key AI-native features while elevating your team's output.
• Ensure cross-pillar design coherence — connect the provider EHR experience seamlessly with patient-side flows and marketplace capabilities (search, booking, onboarding).
• Prototype with Claude Code/Cursor and MagicPatterns to build and iterate on flows and IAs. Let AI generate the pixels and code while you define the right patterns, behaviors, and quality. Partner with product and eng to decide when to move into production.
• Conduct research and directly talk to providers to validate solutions, with the research team's support.
• Contribute to the design system and culture — share your AI practice, prompts, and patterns with the broader design team.

Below are additional experiences we think help leaders succeed at Headway:

• 5+ years leading a design team for complex B2B SaaS platforms with consumer-grade UX.
• Experience with hyper-growth startups (Series C+) and larger companies with mature design practices. Know what good looks like for building an empowered design team.
• Proven track record partnering with product managers, engineers, and leadership to drive experience vision and influence organizational direction through design thinking.
• Experience designing AI-native or AI-augmented product experiences — not just adding AI features, but rethinking workflows around what AI makes possible.
• Portfolio demonstrating both high-craft individual work and systematic approaches to design at scale.

Compensation and Benefits:

The expected base pay range for this position is $249,600 - $312,000 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