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Principal Product Designer, Payer
Headway Remote (🇺🇸 San Francisco, California, United States of America)
Lead the design vision and execution for the Payer group to ensure clinical excellence and coding accuracy. Partner with product and engineering leadership to define the payer strategy and roadmap using AI-forward workflows.
Responsibilities
- Operate as a group lead in close partnership with the Head of Payer Product and Engineering Director to define the payer strategy and roadmap
- Translate regulatory requirements and clinical standards into intuitive, human-centered experiences
- Design for multiple audiences: providers receiving feedback, and payers evaluating the 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 defining 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 AI practice, prompts, and patterns with the design team
Requirements
- 8+ years of experience as a product designer, with experience designing for operational tools, regulated workflows, or multi-sided platforms
- Deep experience building complex systems with strong craft
- Strong portfolio showing systems thinking and ability to ship elegant, cohesive experiences
- Experience designing for multiple audiences, including providers and payers
- Familiarity with AI tools like Claude, Cursor, and MagicPatterns
- Excellent communication, documentation, and presentation skills
- Understanding of accessibility standards (WCAG) and commitment to inclusive design
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
Key Skills
About Headway
Headway is building a new mental healthcare system that everyone can access making it easy for therapists to accept insurance and grow their practice. 1 in 4 people in the US have a treatable mental health condition, but the vast majority do not get the care they need. The primary reason is cost: the majority of therapists do not accept insurance, meaning paying for therapy is prohibitively expensive for prospective patients. This is where we got our start – Headway has built the first software-enabled network of therapists who accept health insurance, making it easy for therapists to grow their practices, and possible for patients to find quality care they can afford. Headway was founded in 2019 and are now powering 600,000+ appointments per month. To scale its vision, Headway has raised over $325 million in funding from a16z (Andreessen Horowitz), Thrive, Accel, and GV (formerly Google Ventures), Spark Capital, Forerunner Ventures and Health Care Service Corporation. Join us, a
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