Design Director, Provider Experience

1 in 4 people in the US have a treatable mental health condition but most providers dont accept insurance making therapy too expensive for most people. Headways 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. Weve automated that.

But were going further. Over 75000 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 arent just a billing layer; we are becoming the platform where care actually happens.

Were 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:

Headways 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 were reimagining these workflows with AI at the center: transcript-powered session notes AI-enabled scheduling co-pilot features etc.

Were 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. Were looking for a design leader whos 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 teams 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 teams 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 $249600 - $312000based on a variety of factors including qualifications experience and geographic 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 teams 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.

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