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.

Revenue Engine is the group that owns it. We're the systems of record and the systems of movement for Headway's money: the billing platform that decides and commits what everyone owes, and the claims platform that exchanges that truth with every payer we work with. When we're right, providers get paid on time, patients get bills they can trust, and Headway can close its books quickly. When we're not, a person has to figure out why; today, more often than we'd like, that's exactly what happens.

Our work is to take systems that are largely right and making them provably right. Explainable after the fact, resilient to the failure of any one component, and correct by construction rather than by human review. It's also work where "correct" is genuinely hard to define. Payers are fickle counterparties: they respond inconsistently, silently, partially, late, or in ways that contradict what they told us last month. Some of the most interesting engineering in this group is deciding what a system should believe when the outside world won't give it a straight answer, and making that belief auditable.

We're hiring two Engineering Managers into Revenue Engine. Both roles lead a team end-to-end, and report to a leader who will give you the autonomy to run it while being a close thought partner. We're a technical engineering org: managers here lead through credibility in design reviews, not through distance from the work.

The two teams

Claims Platform

Claims Platform owns the round-trip between Headway and the payer / clearinghouse ecosystem. Outbound: reliably transmitting claims. Inbound: interpreting whatever comes back: 835 remittances, 277 claim statuses, RARC/CARC codes, rejections, and the long tail of payer responses that don't fit any of those neatly. And in between: recording the result faithfully, so that billing, collections, and the provider and patient experience all operate against the same source of truth.

Why it's interesting: durable workflow orchestration on infrastructure that moves real money, a clean financial-integrity domain, real-time payer-response processing, and a north-star metric: what fraction of appointments get a clear, conclusive payer response with a direct line to company margin.

Billing Infrastructure

Billing Infrastructure owns what Headway believes about an appointment's finances, and when. The billing system is a centralized platform (a suite of APIs) that acts as the conductor for Headway's financial outcomes, modeled after a real-world medical biller. It doesn't own how each responsibility is calculated; it owns orchestrating the specialists that do, in the right order, and committing the result. Two functions: compute (orchestrate patient responsibility, payer responsibility, and provider payout across the teams that own each input) and commit (write those results, and the inputs behind them, as immutable snapshots so any financial commitment is fully explainable after the fact).

Why it's interesting: designing the state machine that decides which financial actions an appointment is eligible for and in what order; guardrail APIs that can refuse a write the domain doesn't allow yet; immutable snapshots of every input and output, so a commitment made months ago can be reconstructed and explained exactly; a shadow mode that lets other teams simulate pricing and billing logic (and compare ML models) against real data without ever committing a financial outcome; and the non-happy paths that make it real, where a refiling, a fee-schedule change, or a correction has to reopen settled state and re-settle it safely.

What you'll own

• An engineering team: hiring to a high bar, growing the people on it, and setting the culture your team operates by.
• A core surface of Headway's financial systems: a platform other teams depend on, and a roadmap you co-own with your product partner.
• Technical direction: architecture, build-vs-buy trade-offs, reliability targets, data-model decisions, and the standard the team operates to.
• Correctness and operability: the metrics that define "right" for your domain, the observability to prove it, incident response and on-call, and the steady conversion of manual toil into automation.
• Cross-functional partnership: with the other Revenue Engine teams, with the platform teams whose inputs and outputs you depend on (benefits, payments, payouts, corrections, claims operations), and with Finance and Accounting, who consume your systems' output as the company's financial record.

Who you are

We're looking for engineering team leaders and people managers who are product-minded, data-informed, and drawn to systems where correctness is the product. As an Engineering Manager in Revenue Engine, you'll work closely with Engineering Leadership, Product, Data, Operations, and Finance to shape how Headway records and moves money. This is an exciting opportunity for a passionate, mission-aligned engineering leader to make an immediate impact at a high-growth company.

Below are additional experiences we think help engineering managers succeed at Headway:

• You have 3+ years of experience as an Engineering Manager, building and leading teams that delivered business outcomes through technical investment.
• You have 3-5+ years of experience as a Software Engineer, with depth in backend and distributed systems: event-driven architectures, workflow orchestration, or high-reliability data pipelines.
• You've led work where correctness and data integrity were non-negotiable (financial systems, payments, billing, claims, or a similarly consequential domain), including migrations you had to de-risk rather than simply schedule.
• You're comfortable defining "correct" in an ambiguous domain: setting the metric, instrumenting it, and defending it as inputs, counterparties, and volume change underneath you.
• You have strong prioritization and roadmap judgment, and you can sequence work for a small team against a clear metric while managing real dependencies on other teams.
• You're technical enough to be a credible thought partner in a design review, and you'd rather be close to the architecture of a money-movement system than removed from it.
• You've built durable partnerships with non-engineering stakeholders (operations, finance, or compliance) whose work depends on what your systems produce.

Nice to have: healthcare claims, EDI or clearinghouse experience; fintech or payments background; experience standing up observability and SLAs on a system that didn't have them; experience growing a small team into a larger one.

Our interview process

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!

Compensation and Benefits:

The expected base pay range for this position is $222,800 - 278,500, 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