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'll be the design anchor for the entire group focused on building the experiences that uphold this trust.

Responsibilities

• Lead the design vision and execution for how we support clinical excellence, ensure coding accuracy, and provide meaningful feedback to providers to influence their behavior—all while maintaining the provider experience that makes Headway different.
• 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.
• Operate as a group lead in close partnership with Head of payer product and Eng director to define the payer strategy and roadmap.

Requirements

• 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).
• Experience shipping products that balance competing constraints—user needs, business requirements, regulatory obligations.
• Precision in visual and interaction design work.
• Knowledge that good craft isn't decorative—it's the grammar that makes complex systems understandable and usable.
• Thriving in complexity and ambiguity.
• Comfortable with incomplete requirements and use design to help clarify and define the problem.
• Ability to scope work appropriately, knowing when to prototype quickly and when to invest in thorough exploration.
• Balancing strategic thinking with hands-on execution—you can develop the vision and then roll up your sleeves to execute it.
• Ai fluency—actively using AI tools like Claude, Cursor, and MagicPatterns to prototype and stay involved through launch and iteration directly in code.

Qualifications

• Exceptional problem-solving skills.
• Strong collaboration and communication skills.
• Experience with user research and usability testing.
• Understanding of healthcare regulations and clinical standards.
• Experience with design systems and design principles.

Skills

• Strong understanding of UX/UI design principles.
• Experience with design tools such as Sketch, Figma, Adobe XD, etc.
• Experience with prototyping tools like Claude, Cursor, and MagicPatterns.
• Experience with design systems and design principles.
• Experience with design thinking methodologies.

Benefits

• Compensation range: $249,600 - $312,000 based on qualifications, experience, and geographic location.
• Equity compensation.
• Medical, Dental, and Vision coverage.
• HSA / FSA.
• 401K.
• Work-from-Home Stipend.
• Treatment 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.