Headway
Healthcare
DesignDirector,ProviderExperience
Neural analysis suggests this role is
optimal for Director candidates.
“Design Director, Provider Experience at Headway. Skills: Provider EHR, AI-native practice, Design leadership. Drive EHR experience strategy. Drive EHR experience vision”
What You'll Achieve.
Make Headway partner; Build entire practice
Industry & Context.
Experience tradeoffs; Quality tradeoffs
What They're Looking For.
Must Have
5+ years leading design team, Experience with hyper-growth startups, Experience with mature design practices, Proven track record partnering with PMs, Proven track record partnering with engineers, Proven track record partnering with leadership, Experience designing AI-native experiences, Experience designing AI-augmented experiences, Portfolio demonstrating high-craft work, Portfolio demonstrating systematic approaches
Nice to Have
Series C+ startup experience
What You'll Do.
Drive EHR experience strategy
Drive EHR experience vision
Partner with engineering
Partner with senior leadership
Define AI-native experience
Own strategic initiatives
Lead AI-native feature design
Ensure design coherence
Connect EHR experience
Connect patient flows
Connect marketplace capabilities
Prototype with Claude Code
Prototype with Cursor
Prototype with MagicPatterns
Contribute to design system
Contribute to design culture
How You'll Work.
Team & Collaboration
Partner with product; Partner with engineering; Partner with leadership; Cross-pillar design coherence; Partner with product; Partner with eng
Full Job Description
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 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 l
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