[Hiring] Staff Product Designer @Headway

Role Description

Group practices are one of Headway's biggest growth levers — and one of its most complex design challenges. Unlike solo providers, group practices operate through owners, admins, supervisors, and supervisees, each with different permissions, workflows, and goals. A single group practice might onboard dozens of providers simultaneously, manage supervisory billing relationships across multiple states, and need practice-level reporting that doesn't exist today.

This is also a massive business opportunity. Supervisory billing — enabling provisionally licensed therapists to bill insurance through Headway — represents a ~250K new provider TAM and over $100M in annual revenue potential. It's the #2 reason we lose group practice sales (after rates), and we're just getting started: we launched in-product onboarding in Q1 and are expanding state-by-state throughout 2026.

As a Staff Product Designer for Group Practices, you'll be the design anchor for the only segment-based pod at Headway. You won't just own a surface — you'll own a customer. That means designing across the full lifecycle:

• How group practices discover and join Headway
• How they onboard and activate supervisees
• How they manage packaging tiers and track practice performance

You'll think like a business builder — understanding the revenue model, making sharp prioritization calls, and designing product experiences that directly drive growth.

We're building an AI-first design team at Headway. Designers are expected to use AI tools like Claude, Cursor, and MagicPatterns to prototype and stay involved through launch and iteration directly in code. We're looking for designers who are already working this way and see AI as a primary part of their workflow.

In this role, you will:

• Own the design of the group practice experience end-to-end — from onboarding and supervisory billing, to packaging and SLA compliance, to practice management and admin tooling.
• Drive supervisory billing from early product to nationwide scale — design the onboarding, activation, and in-product experience for supervisors and supervisees as we expand from NY to all 50 states.
• Design for admins and owners as your primary persona — build bulk workflows, role-based views, multi-provider management, and practice-level analytics that solo-focused products don't support.
• Adapt platform-wide launches for group practices — ensure they work for the group practice context, often requiring fundamentally different design approaches.
• Start in planning mode, using tools like Claude.ai to clarify the problem space, understand data, and test initial assumptions.
• Prototype with Claude Code/Cursor and MagicPatterns to build and iterate on flows and IAs.
• Partner with product & Eng to decide when to move into production.
• Partner closely with Sales and Customer Success — translate their insights into product direction and design decisions.
• Contribute to the design system and culture — share your AI practice, prompts, and patterns with the design team.

Qualifications

• 8+ years of product design experience, with significant time spent designing for multi-user systems with different roles and permissions (admins, operators, end users).
• 0→1 product experience — you've designed new product lines, validated business models through design, or taken a product area from early concept to scale.
• Think like a business builder — you understand revenue models, can connect design decisions to business outcomes, and make sharp prioritization calls about where design effort creates the most value.
• Have designed for platforms or marketplaces where segment-specific needs must be balanced with platform consistency — you know when to customize and when to unify.
• Bring strong visual and interaction design craft across both growth surfaces (onboarding, activation) and product surfaces (dashboards, tooling, operational workflows).
• Are comfortable partnering with Sales and CS as key stakeholders — not just PM and Eng — and translating customer relationships into product insights.
• Are comfortable with AI prototyping tools (Claude Code, Cursor, MagicPatterns) and see them as a core part of how you work.
• Want your work to make a meaningful difference in people's lives — by helping group practices thrive on Headway, you're expanding access to affordable mental healthcare at scale.

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