Senior / Staff Product Designer - Provider

HeadwayNew York, NY
Remote

About The Position

Headway is building a new mental healthcare system that is accessible and affordable for everyone. We started by addressing the insurance barrier, automating the administrative work for providers. Now, over 75,000 providers in all 50 states use our software to manage their practices and serve over 1 million patients. We are developing the best tools for therapists, enhancing the experience of finding a therapist, and building a scalable platform for care delivery. We are a Series D company with over $325M in funding and are seeking exceptional individuals to help us achieve our mission. We aim to make your time here the most meaningful of your career and to collectively improve mental healthcare.

Requirements

  • Senior: 5+ years of product design experience with a portfolio showcasing strong craft, structured thinking, and measurable business impact.
  • Staff: 8+ years of product design experience with a portfolio showcasing exceptional craft, systems thinking, and measurable business impact.
  • Experience designing B2B or professional tools for expert users requiring efficiency and reliability.
  • Systems thinking ability to shape complex, state-heavy problems into coherent experiences.
  • Product strategy instinct, shaping product direction from customer insights and contributing a unique point of view.
  • Fluency in experimentation, having run multi-sprint experiment arcs against real metrics.
  • Fluency with AI prototyping tools, treating them as core to your workflow.
  • Motivation by Headway's mission to make mental healthcare accessible and affordable.
  • Experience with 0→1 work, comfortable defining new product surfaces from scratch.
  • Experience designing agentic or AI-powered workflows (e.g., clinical documentation, intelligent billing, replacing manual processes with AI).
  • Ability to hold complex, multi-actor provider workflows in mind and design with awareness of the full pipeline.
  • Experience elevating designers through mentorship, critique, or high-quality work.

Responsibilities

  • Own the provider product experience end to end, from problem framing through launch and iteration.
  • Act as the primary design voice on your team.
  • Prototype and test ideas quickly using AI tools like Claude Code and Cursor, where AI generates pixels and prototypes, and you define patterns, behaviors, and quality standards.
  • Partner closely with product managers, engineers, and researchers to shape product scope and priority.
  • Design for provider workflows including credentialing, scheduling, clinical documentation, and billing, making complex tasks fast and reliable.
  • Run experiments with clear success metrics, measuring task completion, error rates, and provider satisfaction, treating negative results as findings.
  • Contribute to Helix, our design system, and share AI prompts and patterns with the broader design team.
  • Lead both 0→1 and at-scale work, launching new provider capabilities and improving existing ones.
  • Design AI-native provider experiences such as agentic documentation, intelligent billing automation, and workflows that replace manual processes.
  • Set the standard for AI-native practice on the design team, prototyping in code and staying involved through launch.
  • Mentor other designers, raise the craft bar, and shape the design organization through critique, design system contributions, and shared practices.
  • Influence product direction with design rationale, research, and storytelling, contributing to the provider roadmap.

Benefits

  • 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
  • Holiday Break during the week between December 25th and December 31st
  • Flexible PTO
  • Employee Assistance Program (EAP)
  • Training and professional development
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