Principal Product Designer, Payer

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 70000 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 GV 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

At Headway trust is foundational. Patients trust us to connect them with quality providers. Providers trust us to handle the complexity of insurance. And payers trust us to maintain clinical and coding integrity across our entire network.

As a Principal Product Designer on the Payer group youll be the design anchor for the entire group focused on building the experiences that upholds this trust. Youll lead the design vision and execution for how we support clinical excellence ensure coding accuracy and provide meaningful feedback to providers to influence their behaviorall while maintaining the provider experience that makes Headway different.

Design at Headway is AI forward. 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 designers whore already working this way and see AI as a primary part of their workflow.

In this role youll:

• Operate as a group lead in close partnership with Head of payer product and Eng director to define the payer strategy and roadmap.
• Translate regulatory requirements and clinical standards into intuitive human-centered experiences that make complex requirements feel manageable
• Design for multiple audiences: providers receiving feedback and payers evaluating our network

• Start in planning mode use tools like and internal AI platform to clarify the problem space understand data and initial assumptions.
• Prototype with Claude Code/Cursor and MagicPattern to build and iterate on the flows and Information Architecture. Let AI generate the pixels and code while you define the right patterns behaviors and quality. Partner with product & Eng to decide when to move into production.
• Conduct research and directly talk to customers to validate the solution for most of BAU projects with the research teams support.
• Contribute to the design system and culture share your AI practice prompts and patterns with the design team.

Youll be a great fit if you:

Have deep experience building complex systems with strong craft

• 8 years as a product designer with experience designing for operational tools regulated workflows or multi-sided platforms
• Youve shipped products that balance competing constraintsuser needs business requirements regulatory obligations
• Your visual and interaction design work is polished and precise
• You know that good craft isnt decorativeits the grammar that makes complex systems understandable and usable

Thrive in complexity and ambiguity

• Youre comfortable with incomplete requirements and use design to help clarify and define the problem
• You can scope work appropriately knowing when to prototype quickly and when to invest in thorough exploration
• You balance strategic thinking with hands-on executionyou can develop the vision and then roll up your sleeves to execute it

Youre AI fluent

• Youre actively using AI tools like Claude Cursor and MagicPatterns to prototype and stay involved through launch and iteration directly in code.

Compensation and Benefits:

The expected base pay range for this position is $249600 - $312000 based 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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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 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 @ 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.