About the Role

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. 

In This Role, You Will

• 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 $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