Headway
Healthcare
DesignDirector,ProviderExperience
Neural analysis suggests this role is
optimal for Director candidates.
“Design Director, Provider Experience at Headway. Skills: Provider EHR experience, AI-native design, Design vision. Drive provider EHR experience strategy. Drive provider EHR experience vision”
Industry & Context.
What They're Looking For.
Must Have
5+ years leading design team, Experience with hyper-growth startups, Experience with larger companies, Portfolio demonstrating high-craft work, Portfolio demonstrating systematic approaches
Nice to Have
Consumer-grade UX for B2B SaaS, Experience designing AI-native experiences, Experience designing AI-augmented experiences
What You'll Do.
Drive provider EHR experience strategy
Drive provider EHR experience vision
Partner with engineering
Partner with senior leadership
Define AI-native practice management experience
Make experience tradeoffs
Make quality tradeoffs
Own strategic design initiatives
Lead design of AI-native features
Elevate team's output
Ensure cross-pillar design coherence
Connect provider EHR experience
Connect patient-side flows
Connect marketplace capabilities
Prototype with Claude Code
Prototype with Cursor
Prototype with MagicPatterns
Let AI generate pixels
Decide when to move to production
Contribute to design system
Contribute to design culture
How You'll Work.
Team & Collaboration
Cross-functional teams; Product and engineering; Senior leadership
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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