Senior Engineering Manager, Billing Infrastructure

1 in 4 people in the US have a treatable mental health condition but most providers dont accept insurance making therapy too expensive for most people. Headways 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. Weve automated that.

But were going further. Over 90000 providers across all 50 states run their practice on our software serving over 2.6 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 and building much of it with AI. We arent just a billing layer; we are becoming the platform where care actually happens.

Were 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.

The Role

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 appointments 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.

About Engineering at Headway

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

About this role

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 youll 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; youll 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. Youll 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 systems output as the companys 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.

Who you are

Were looking for a senior engineering leader with the technical depth to shape a complex financial platform and the organizational credibility to govern it. Youll 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 57 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.

• Youve 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.

• Youve 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.

Our interview process

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

• Initial screen: Youll connect with someone in recruiting so you can learn more about the team Headways mission and exciting growth and we can get a better idea of your background.

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

• Final rounds: Youll 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 its like to work at Headway.

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

Compensation and Benefits

The expected base pay range for this position is $265200 - $331500 based on a variety of factors including qualifications experience and geographic 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 teams 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 teams 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 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 @ 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.

Required Experience:

Manager