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

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