Principal Product Designer, Payer

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, you will anchor design for the entire group, lead the design vision, and execute on experiences that ensure clinical excellence, accurate coding, and meaningful provider feedback—all while maintaining the unique provider experience that differentiates Headway. Design at Headway is AI‑forward. Designers are expected to use AI tools like Claude, Cursor, and MagicPatterns to prototype and involve them through launch and iteration directly in code. We prefer designers who already integrate AI as a primary part of their workflow. In This Role, You’ll 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 that make complex requirements manageable. Design for multiple audiences: providers receiving feedback and payers evaluating our network. Start in planning mode, using tools such as Claude.ai and the internal AI platform to clarify the problem space, understand data, and establish initial assumptions. Prototype with Claude Code/Cursor and MagicPattern to build and iterate on flows and information architecture; let AI generate pixels and code while you set the patterns, behaviors, and quality. Partner with product and engineering to decide when to move into production. Conduct research and directly talk to customers to validate solutions for most BAU projects, with the research team’s support. Contribute to the design system and culture, sharing AI practice, prompts, and patterns with the design team. You’ll 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. You have shipped products that balance competing constraints—user needs, business requirements, regulatory obligations. Your visual and interaction design work is polished and precise. You understand that good craft is not decorative—it is the grammar that makes complex systems understandable and usable. Thrive in complexity and ambiguity You are comfortable with incomplete requirements and use design to clarify and define problems. You can scope work appropriately, deciding when to prototype quickly and when to invest in thorough exploration. You balance strategic thinking with hands‑on execution—you can develop vision then roll up your sleeves to execute. You’re AI fluent You actively use 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 $249,600 - $312,000, based on qualifications, experience, and geographic location. This role may also be eligible for an equity grant, depending on position and level. We offer a comprehensive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. 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, plus a holiday break between December 25th and 31st Flexible PTO Employee Assistance Program (EAP) Training and professional development Equal Opportunity Statement We believe a team’s strength is in its people and 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 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. #J-18808-Ljbffr