Principal Product Designer, Payer

Headway•San Francisco, NY

2d•Remote

About The Position

Headway's mission is to fix the mental healthcare system by building a new system everyone can access, starting with solving the barrier of insurance. The company has automated the administrative work of credentialing, claims, and payment reconciliation. Over 70,000 providers across all 50 states use Headway's software, serving over 1 million patients. Headway is building tools for therapists to run their practice, improving the experience of finding a therapist, and investing in platform foundations for scale. The company is a Series D company with over $325M in funding and is looking for exceptional people to help achieve its mission. As a Principal Product Designer on the Payer group, you will be the design anchor for the group focused on building experiences that uphold trust with patients, providers, and payers. You will lead the design vision and execution for supporting clinical excellence, ensuring coding accuracy, and providing meaningful feedback to providers to influence their behavior, all while maintaining the provider experience. Design at Headway is AI forward, with designers expected to use AI tools like Claude, Cursor, and MagicPatterns to prototype and stay involved through launch and iteration directly in code. The company is looking for designers who are already working this way and see AI as a primary part of their workflow.

Requirements

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
You've shipped products that balance competing constraints—user needs, business requirements, regulatory obligations
Your visual and interaction design work is polished and precise
You know that good craft isn't decorative—it's the grammar that makes complex systems understandable and usable
Thrive in complexity and ambiguity
You're 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 execution—you can develop the vision and then roll up your sleeves to execute it
You’re AI fluent
You’re actively using AI tools like Claude, Cursor, and MagicPatterns to prototype and stay involved through launch and iteration directly in code.

Responsibilities

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 Claude.ai 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 team’s support.
Contribute to the design system and culture, share your AI practice, prompts, and patterns with the design team.

Benefits

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