Senior / Staff Product Designer - Provider

Headway’s mission is to build a new mental healthcare system everyone can access by automating insurance admin work for providers. We're hiring Senior and Staff Product Designers to own the provider experience at Headway. The work calls for strong craft, sharp product instincts, deep customer obsession, and real fluency in an AI-native environment where prototyping in code is core to the role. Designers use Claude Code and Cursor to prototype, ideate, and ship improvements. Our mission is to help providers build a thriving practice on Headway that practically runs itself, on product surfaces that are fast, reliable, and a delight to use.

Responsibilities

Own the provider product experience end to end; Prototype and test ideas quickly with Claude Code, Cursor, or AI tool of choice; Partner closely with product managers, engineers, and researchers; Design workflows for provider tasks (credentialing, scheduling, clinical documentation, billing); Run experiments with clear success metrics; Contribute to Helix design system and share AI prompts/patterns; Staff level: Lead both 0→1 and at-scale work; Staff level: Design AI-native provider experiences; Staff level: Set the standard for AI-native practice; Staff level: Mentor other designers; Staff level: Influence product direction

Requirements

5+ years of product design experience; Portfolio showing strong craft, structured thinking, and measurable business impact; Track record of owning complex surfaces end to end; Experience designing B2B or professional tools where users are experts who need efficiency and reliability; Systems thinker; Product strategy instinct; Fluent in experimentation with multi-sprint experiment arcs; Fluent with AI prototyping tools (e.g., Claude Code, Cursor); Motivated by Headway's mission; Staff level: 8+ years of product design experience; Staff level: 0→1 work defining provider-facing product surfaces; Staff level: experience designing agentic or AI-powered workflows; Staff level: mentorship and elevating other designers; Staff level: influence product direction

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 plus Holiday Break; Flexible PTO; Employee Assistance Program (EAP); Training and professional development