Staff Product Manager, Billing Infrastructure

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 60,000 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.

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:

As the Staff Product Manager for our Billing Infrastructure, you'll be responsible for building the backbone that powers patient payments, provider payouts, insurance claims, and accounting. You'll own the strategy to transform our billing systems from fragmented processes into a unified, scalable platform that handles complex healthcare payment flows. Working closely with Engineering, Data, Finance, Operations, and Compliance teams, you'll build systems that process millions of transactions while maintaining complete accounting accuracy.

What you'll do at Headway:

• Own the billing infrastructure strategy and roadmap to achieve goals around payment processing reliability, accounting accuracy and financial compliance


• Build systems that handle complex multi-party payment scenarios including patient payments, provider payouts, and insurance claims


• Work with the Data and Engineering team to monitor and optimize payment success rates through deep data analysis, identifying trends and implementing improvements to reduce payment friction


• Drive technical decisions on architecture and platform scalability with Engineering teams


• Collaborate with Finance, Ops and Engineering teams on developing automated processes that reduce manual intervention and improve accounting accuracy

You'll be great for this role if you:

• Platform and billing experience: You have 7+ years building billing platforms or accounting systems, preferably in healthcare, fintech, or marketplaces with complex payment flows. You understand the intricacies of payment processing, ledger management, and accounting reconciliation


• Technical depth: You're comfortable diving deep with engineering teams on complex technical problems and can drive hard architectural decisions


• Cross-functional leadership: You've led initiatives requiring difficult tradeoffs between system reliability, compliance requirements, and user experience. You can influence stakeholders across Finance, Legal and Compliance.


• Systems thinking: You excel at analyzing complex workflows to identify inefficiencies and drive systematic improvements

The expected base pay range for this position is $215,900 - $254,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance-based variable compensation and 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

#LI-RJ1

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 employees work remotely across the US, with the option to work from offices in New York City, San Francisco and Seattle. Headway participates in E-Verify. To learn more, click here.