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HeadwayHeadwayNew York, NY

Principal Product Designer, Payer

Leads design vision and execution for payer group, building experiences for clinical excellence, coding accuracy, and provider feedback using AI tools like Claude and Cursor. Requires 8+ years designing complex, regulated systems with strong craft and AI fluency.

250k – 312k/yr
Remote8+ YOEProduct Design

About the role

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.

Requirements

  • 8+ years as a product designer, with experience designing for operational tools, regulated workflows, or multi-sided platforms.
  • Shipped products that balance competing constraints—user needs, business requirements, regulatory obligations.
  • Visual and interaction design work is polished and precise.
  • Comfortable with incomplete requirements and use design to help clarify and define the problem.
  • Scope work appropriately, knowing when to prototype quickly and when to invest in thorough exploration.
  • Balance strategic thinking with hands-on execution.
  • AI fluent: Actively using AI tools like Claude, Cursor, and MagicPatterns to prototype and stay involved through launch and iteration directly in code.

Compensation and Benefits

Base pay range: $249,600 - $312,000, based on qualifications, experience, and location. Eligible for equity grant.

  • Equity compensation
  • Medical, Dental, and Vision coverage
  • HSA / FSA
  • 401K
  • Work-from-Home Stipend
  • Therapy Reimbursement
  • 16-week parental leave
  • Carrot Fertility reimbursement
  • 13 paid holidays + Holiday Break
  • Flexible PTO
  • Employee Assistance Program (EAP)
  • Training and professional development

Skills

FigmaClaudeCursorMagicpatternsAi PrototypingDesign SystemsInteraction DesignVisual DesignUser ResearchInformation Architecture

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