Headway

Healthcare

DesignDirector,ProviderExperience

$250–312k San Francisco, California, United States FULL TIME
Market Sentiment
HIGH DEMAND

Neural analysis suggests this role is
optimal for Director candidates.

The Brief

“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.

Healthcare
Problems you'll solve

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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