Headway

Healthcare

DesignDirector,ProviderExperience

$180–270k ~AI est. United States Remote Friendly
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 experience, AI-native design, Design vision. Drive provider EHR experience strategy. Drive provider EHR experience vision”

Industry & Context.

Healthcare

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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