Job Description

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. 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.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. 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 This 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.

You Will

• 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.

Who You Are

• 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.

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 participates in E-Verify. To learn more, click here.

A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @ findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.