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 upholds this trust. You'll 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.

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. We’re looking for designers who’re already working this way and see AI as a primary part of their workflow. 

In this role, you'll:

• 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.

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'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. 

Compensation and Benefits:

The expected base pay range for this position is $249,600 - $312,000, based on a variety of factors including qualifications, experience, and geographic location. In 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