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 the team to consistently make strong experience and quality tradeoffs.
- Own strategic design initiatives hands-on as a player-coach, lead the design of key AI-native features while elevating your team's output.
- Ensure cross-pillar design coherence — connect the provider EHR experience seamlessly with patient-side flows and marketplace capabilities (search, booking, onboarding).
- Prototype with Claude Code/Cursor and MagicPatterns to build and iterate on flows and IAs. Let AI generate the pixels and code while you define the right patterns, behaviors, and quality. Partner with product and eng to decide when to move into production.
- Conduct research and directly talk to providers to validate solutions, with the research team's support.
- Contribute to the design system and culture — share your AI practice, prompts, and patterns with the broader design team.
Below are additional experiences we think help leaders succeed at Headway:
- 5+ years leading a design team for complex B2B SaaS platforms with consumer-grade UX.
- Experience with hyper-growth startups (Series C+) and larger companies with mature design practices. Know what good looks like for building an empowered design team.
- Proven track record partnering with product managers, engineers, and leadership to drive experience vision and influence organizational direction through design thinking.
- Experience designing AI-native or AI-augmented product experiences — not just adding AI features, but rethinking workflows around what AI makes possible.
- Portfolio demonstrating both high-craft individual work and systematic approaches to design at scale.
Compensation and Benefits:
The expected base pay range for this position is $249,600 - $312,000 based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.
We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.
- Benefits offered include:
- Equity compensation
- Medical, Dental, and Vision coverage
- HSA / FSA
- 401K
- Work-from-Home Stipend
- Therapy Reimbursement
- 16-week parental leave for eligible employees
- Carrot Fertility annual reimbursement and membership
- 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
- Flexible PTO
- Employee Assistance Program (EAP)
- Training and professional development
We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.
Headway participates in E-Verify. To learn more, click here.
A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.
Skills Required
- 5+ years leading a design team for complex B2B SaaS platforms with consumer-grade UX
- Experience designing AI-native or AI-augmented product experiences and rethinking workflows around AI
- Proven track record partnering with product managers, engineers, and leadership to drive experience vision
- Portfolio demonstrating both high-craft individual work and systematic approaches to design at scale
- Experience hiring, attracting, coaching, and managing a team of designers
- Ability to prototype and iterate using AI tools and code (Claude/Claude Code, Cursor, MagicPatterns)
- Experience conducting research and talking directly to providers or end users to validate solutions
- Experience contributing to and evolving a design system and sharing design practices across a team
- Experience at hyper-growth startups (Series C+) or larger companies with mature design practices
What the Team is Saying
Headway Compensation & Benefits Highlights
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Healthcare Strength — Medical, dental, and vision plans offer multiple Cigna options with the employer covering a majority of premiums. Mental-health support includes an HRA reimbursing eligible therapy costs up to $2,100 per year and access to an EAP.
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Parental & Family Support — Up to 16 weeks of fully paid parental leave is available to eligible full-time employees. Family-forming support is enhanced through a partnership with Carrot Fertility.
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Leave & Time Off Breadth — Flexible/generous PTO is paired with 56 hours of paid sick time and 13 paid holidays. A company year-end holiday break (Dec 25–31) is also noted.
Headway Insights
What We Do
Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.
Why Work With Us
The demand for mental health care has never been higher, underscoring the need for solutions like Headway that increase accessibility to clinical care. We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem.
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Headway Offices
Remote Workspace
Employees work remotely.
Headway employees work remotely across the US, with the option to work from offices in New York City, San Francisco and Seattle.
