Staff Product Manager, Billing Infrastructure

About the role

Behavioral health is booming, demand keeps growing, but getting paid for it keeps getting harder. For providers, getting paid for it is the hard part. Reimbursement is wildly variable and timely, in-full payment can be the difference between a practice staying open and a patient losing access to care. That's the stakes underneath the systems you'll build, for Headway's 80K+ providers, getting billing right isn't back-office hygiene, it's what keeps their doors open. You will own two connected halves of Headway's billing platform. First, building the billing system into an engine where every new appointment comes out right, going forward and second, turning that financial data into the datasets, dashboards, and general-ledger outputs Finance and Accounting rely on to close the books. Today, this infrastructure is fragmented - manual reconciliation, undetected payment failures, and limited real-time visibility create operational drag and growing risk as we scale. Your job is to turn it into a unified platform that Finance, Engineering, Support, and Compliance can all build on and trust. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens. You will partner with Data and Engineering to monitor payment/reconciliation health and drive systemic fixes, not point patches.

Key facts

What you'll do

• Prevent breakage going forward: define the billing state machine, enforced handoffs, and guardrails so new appointments come out right without manual intervention.
• Make financial data usable: build the trusted datasets, dashboards, and general-ledger/audit outputs Finance and Accounting rely on to close the books - moving time-to-close from yearly to quarterly to monthly.
• Own the billing platform architecture and roadmap - the ledger, reconciliation, and data-integrity systems underneath patient charges, provider payouts, and payer collections.
• Partner with Data and Engineering to monitor payment/reconciliation health and drive systemic fixes, not point patches.
• Partner with Finance, Accounting, and Compliance so financial reporting and audit prep are trustworthy and fast, not multi-week fire drills.
• Serve as the platform other teams build on - Provider Payouts, Payer Collections, and Pricing consume your platform's guarantees without you owning their roadmaps.
• Define and enforce the canonical data model for billing, ensuring consistency across providers, payers, and payment flows.
• Lead cross-functional alignment on billing policies, payment rules, and exception handling to ensure clarity at scale.
• Drive measurable improvements in payment accuracy, reconciliation speed, and insight into revenue leakage.
• Translate complex billing workflows and failures into clear narratives for executives, Finance, and Support.
• Design for auditability and traceability so every transaction can be inspected and explained.
• Balance pragmatic short-term fixes with long-term platform investments that reduce future operational burden.
• Work closely with providers to understand pain points and translate them into product requirements for billing infrastructure.
• Champion testing and observability for billing changes to prevent regressions in production.

Requirements

• 8+ years building billing platforms, ledgers, or accounting systems - ideally in healthcare, fintech, or marketplaces with complex payment flows.
• Comfortable diving deep with engineering teams on complex technical problems and driving hard architectural decisions.
• Trusted partner to Finance, Accounting, and Compliance, not just Engineering - you can translate ledger reality into language each audience acts on.
• Strong and clear communicator - clear and concise translating between accounting/ops language and engineering language.
• Experience defining and operating billing state machines, reconciliation logic, and general-ledger integrations in a high-volume environment.
• A track record of building systems where data integrity is non-negotiable and errors are detectable and recoverable.
• Comfort with ambiguity and the ability to make progress without perfect information in fast-moving, startup environments.
• Willingness to deep-down into specifics of payment flows, reconciliation differences, and regulatory constraints impacting billing.

Nice to have

• Experience in mental health, insurance, or benefits administration.
• Background working with compliance, legal, or audit teams on financial controls.
• Familiarity with electronic funds transfer (EFT), electronic remittance advice (ERA), and 835/837P data formats.
• Experience implementing idempotency, retries, and exactly-once processing for billing-critical workflows.
• Knowledge of revenue recognition rules and how they apply to recurring SaaS billing in multi-currency environments.

Practical notes

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