Staff Product Designer, Group Practices

You will own the design of the group practice experience end-to-end, including onboarding and supervisory billing. Additionally, you will drive the design for practice management and admin tooling, ensuring alignment with business goals.

Responsibilities

• 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 — when Headway ships packaging, identity verification, or onboarding improvements, you'll 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, who have deep relationships with group practice customers — 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

Requirements

• 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

Key Skills