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Design Director, Provider Experience

1 month, 1 week ago
United States
Full-time
Lead
Design Lead
Design and User Experience
Design Systems Microservices
Apply Now
Headway

Headway

Headway is revolutionizing mental healthcare by connecting patients with therapists who accept insurance, making quality care accessible and affordable for all.

Health Care Providers & Services
251-1K
Founded 2017
$226M raised
View All Jobs 5

Description

  • Drive the provider EHR experience strategy and vision across scheduling, documentation, session experience, and client engagement.
  • Partner with product, engineering, and senior leadership to define what an AI-native practice management experience should look like.
  • Hire, attract, manage, and coach a team of designers while setting a high craft bar.
  • Own strategic design initiatives hands-on as a player-coach and lead key AI-native features.
  • Ensure design coherence across provider EHR, patient-side flows, and marketplace capabilities such as search, booking, and onboarding.
  • Prototype workflows and information architecture using AI tools such as Claude Code, Cursor, and MagicPatterns.
  • Work with product and engineering to determine when prototypes should move into production.
  • Conduct research and speak directly with providers to validate solutions.
  • Contribute to the design system and share AI practices, prompts, and patterns with the broader design team.

Requirements

  • 5+ years leading a design team for complex B2B SaaS platforms with consumer-grade UX.
  • Experience with hyper-growth startups, ideally Series C+, and larger companies with mature design practices.
  • Proven ability to partner with product managers, engineers, and leadership to shape experience vision and influence organizational direction.
  • Experience designing AI-native or AI-augmented product experiences.
  • Portfolio demonstrating both high-craft individual work and systematic design approaches at scale.
  • Experience using AI tools such as Claude, Cursor, or MagicPatterns to prototype and iterate is strongly preferred.
  • Comfort working in a hands-on player-coach role.
  • Ability to work effectively on complex, high-stakes product workflows in a regulated environment.

Benefits

  • Base salary range of $249,600 to $312,000.
  • Potential eligibility for an equity grant.
  • Medical, dental, and vision coverage.
  • HSA / FSA options.
  • 401K retirement savings plan.
  • Work-from-home stipend.
  • Therapy reimbursement.
  • 16-week parental leave for eligible employees.
  • Carrot fertility annual reimbursement and membership.
  • 13 paid holidays plus a holiday break between December 25 and December 31.
  • Flexible PTO.
  • Employee Assistance Program (EAP).
  • Training and professional development.

Interested in this position?

Apply directly on the company website

Apply Now

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