About the role
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 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