Staff Product Designer Payments

This role sits at the intersection of patients providers and insurance designing the billing and payment experiences that make Headway's financial engine feel simple transparent and trustworthy.

This is a complex high-stakes design challenge. A single appointment at Headway touches insurance verification claims processing provider payouts and patient billing — all with different timelines edge cases and failure modes. Today confusion around billing is one of the top drivers of support tickets and a key factor in provider trust.

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’re already working this way and see AI as a primary part of their workflow. 

• Own the end-to-end payment and billing experience across patients and providers. Navigate complexity with systems thinking. Payment flows touch insurance confirmation claims ERA ingestion refunds cancellation fees and provider payouts. You'll map these dependencies and design experiences that absorb complexity rather than expose it.
• Start in planning mode use tools like Claude.ai to clarify the problem space understand data and initial assumptions. 
• Prototype with Claude Code/Cursor and MagicPattern to build and iterate on the 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. 
• Conduct research and directly talk to customers to validate the solution for most of BAU projects with the research team’s support.
• Contribute to the design system and culture share your AI practice prompts and patterns with the design team.

Compensation and Benefits:

The expected base pay range for this position is $212000 - $265000 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

What We Do

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 1 in 4 people in the US have a treatable mental health condition but the majority of providers don’t accept insurance making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. Headway was founded in 2019. Since then we’ve grown into a diverse national network of over 60000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz) Accel GV (formerly Google Ventures) Spark Capital Thrive Capital Forerunner Ventures and Health Care Service Corporation.

Why Work With Us

The demand for mental health care has never been higher underscoring the need for solutions like Headway that increase accessibility to clinical care. 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.

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