Engineering Manager (Revenue Engine)

Headway; San Francisco (CA); On-site; USD 190,000 - 230,000; Full time

Job summary

Headway is building a scalable revenue engine in San Francisco and seeks an Engineering Manager to lead an end-to-end team focused on the billing platform and payer interoperability. You will ensure correct, auditable financial outcomes and partner across product, data, operations, and finance.

You will drive architectural decisions, improve observability, incident response, and automation, and elevate the team's ability to deliver reliable software at scale.

Qualifications

• Experience leading an engineering team end-to-end.
• Ability to partner with product, data, operations, and finance.
• Strong focus on system design and reliability.
• Advocate for data-informed decision making.
• Ability to drive architectural direction and technical credibility.

Responsibilities

• Lead an engineering team end-to-end within Revenue Engine.
• Own technical direction, architecture, and reliability targets.
• Collaborate with product and cross-functional partners to deliver on roadmap.
• Improve observability, incident response, and automation in billing platforms.
• Mentor engineers and shape team culture and growth.

Skills

Engineering management

Cross-functional

Product-minded

Data-informed

System design

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 Engineering at Headway

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

The 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.

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 "right" 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, 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