Design Director, Provider Experience

About the role

This role owns the design vision and execution for the provider EHR experience at Headway. The goal is to make Headway the practice partner that providers choose to build their entire practice on. This involves working closely with product, engineering, and senior leadership to define what an AI-native practice management experience looks like across scheduling, documentation, session experience, and client engagement.

Responsibilities

• Hire, attract, and manage a team of designers.
• Set a high craft bar that inspires senior designers and coaches the team to consistently make strong experience and quality tradeoffs.
• Own strategic design initiatives hands-on as a player-coach, lead the design of key AI-native features while elevating your team's output.
• Ensure cross-pillar design coherence—connect the provider EHR experience seamlessly with patient-side flows and marketplace capabilities (search, booking, onboarding).
• Prototype with AI tools like Claude, Cursor, and MagicPatterns to build and iterate on flows and IAs. Let AI generate the pixels and code while you define the right patterns, behaviors, and quality.
• Partner with product and engineering to decide when to move into production.
• Conduct research and directly talk to providers to validate solutions, with the research team's support.
• Contribute to the design system and culture—share your AI practice, prompts, and patterns with the broader design team.

Qualifications

• 5+ years leading a design team for complex B2B SaaS platforms with consumer-grade UX.
• Experience with hyper-growth startups (Series C+) and larger companies with mature design practices.
• Proven track record partnering with product managers, engineers, and leadership to drive experience vision and influence organizational direction through design thinking.
• Experience designing AI-native or AI-augmented product experiences—rethinking workflows around what AI makes possible.
• Portfolio demonstrating both high-craft individual work and systematic approaches to design at scale.