Staff Product Designer, Payments

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

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.

A single appointment at Headway touches insurance verification, claims processing, provider payouts, and patient billing — all with different timelines, edge cases, and failure modes.

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.