Senior Product Designer, Design Systems

Headway's Mission

One in four people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway's mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

About the Role

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.

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. You're the design anchor for the entire segment.

• 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. Let AI generate the pixels and code while you define the right patterns, behaviors, and quality. 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.

You'll Be a Great Fit If You:

• Have 8+ years of product design experience, with significant time spent designing for multi-user systems with different roles and permissions (admins, operators, end users)

• Have 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

Compensation and Benefits:

The expected base pay range for this position is $212,000 - $265,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.

We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.

• Benefits offered include:

  • 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

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

Headway participates in E-Verify. To learn more, click here.

A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at . Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @ findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.