Senior Engineering Manager, Billing Infrastructure

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.

Lead the platform that owns what Headway believes about the money on every appointment, and when anyone is allowed to act on it. Help drive building our new orchestration layer, a codified financial state machine for an appointment’s financial lifecycle: explicit states, enforced guardrails, automated reconciliation, immutable explainability, and safe simulation of financial logic. A senior, high-leverage platform role at the center of every financial system at Headway, with a documented charter and a direct line to how quickly the company can close its books.

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide.

Every appointment on Headway has a financial story: what the patient owes, what the provider is paid, what the payer is billed, and whether all three ever line up. At 1.5M+ appointments a month, up from 5.6M appointments in all of 2023 to 14.5M in 2025, that story has to be told correctly, automatically, and the same way every time.

As Senior Engineering Manager, you’ll own the technical strategy for the Billing System platform and drive its next chapter. Our new orchestration layer: the codified state machine that knows what state every appointment is in and what actions are allowed next is in design phases now; you’ll play a key role in building and planning from initial to full governance. Beyond orchestration: guardrail APIs that gate other systems’ writes, automated payer remittance ingestion, automatic refunds and recoups, and the non-happy-path machinery (refilings, fee-schedule corrections, settled state that has to reopen and re-settle safely) where the real engineering difficulty lives. You’ll set technical direction across state-machine design, immutable snapshot and explainability guarantees, shadow-mode simulation, and a path toward durable workflow orchestration, while partnering with Finance and Accounting, who consume your system’s output as the company’s financial record.

This is a platform-definition role, not a cleanup role. The billing system already exists and already commits real financial outcomes; the mandate is to extend it into the authority that governs when every financial action can happen, at 1.5M+ appointments a month and accelerating.

We’re looking for a senior engineering leader with the technical depth to shape a complex financial platform and the organizational credibility to govern it. You’ll work closely with Engineering Leadership, Product, Data, Finance, and Accounting to define how Headway records, moves, and stands behind its money.

Below are experiences we think help senior engineering managers succeed in this role:

• You have 5+ years of experience as an Engineering Manager, including experience leading platform or infrastructure teams at scope beyond a single team — multiple teams, a broad cross-org platform mandate, or both.

• You have 5–7+ years of experience as a Software Engineer with depth in backend and distributed systems: financial state machines, event-driven architectures, workflow orchestration, or high-reliability data pipelines in domains where correctness is non-negotiable.

• You’ve led platform work whose customers are other engineering teams — defining contracts, setting standards, and getting peers to build behind guardrails rather than around them.

• You have a track record in domains where data integrity and financial correctness were the product: billing, payments, ledgers, claims, or a similarly consequential platform.

• You’ve partnered with Finance, Accounting, or compliance functions whose work depends on what your systems produce, and you can make that relationship work when interests diverge.

• You have strong prioritization and roadmap judgment and can sequence work across a chain of dependent migrations while managing real cross-team dependencies.

Nice to have: ledger, double-entry, invoicing, or reconciliation systems experience; healthcare billing or EDI exposure; fintech or payments background; experience through external audit or a financial close-cycle transition; has built simulation, shadow-mode, or backtesting infrastructure for consequential financial logic.

After you apply to Headway, here are some details of what to expect during the interview process.

• Initial screen: You'll connect with someone in recruiting so you can learn more about the team, Headway's mission and exciting growth, and we can get a better idea of your background.

• First rounds: You'll meet with an engineering leader on the team to go deeper into your team and people leadership experiences.

• Final rounds: You'll meet team members across product and engineering leadership for multiple behavioral interviews and two technical interviews (System Design & AI Coding), leaving you with a fuller picture of what it's like to work at Headway.

• References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!

The expected base pay range for this position is $265,200 - $331,500, 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

• 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

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.

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.

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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.