Engineering Manager (Claims)

About the Role

Mental health care shouldn't come with surprise bills, and it shouldn't cost providers sleep wondering whether they'll get paid for the work they did. At Headway, getting insurance right — reliably, accurately, and in real time — is the single most leveraged problem we solve. It's the difference between a patient who can afford their first session and one who can't; between a provider who chooses Headway and one who doesn't.

We're hiring an Engineering Manager to lead the Claims Platform team inside Headway's insurance group. Claims Platform owns the round-trip between Headway and the payer / clearinghouse ecosystem: outbound claim submission, inbound response interpretation, and the structured record of the result — the "claim stack." When an upstream decision is made on what, when, and where to file or refile a claim, your team makes sure the connection works, the most useful possible response comes back cleanly from the payer or clearinghouse (e.g. Stedi), and the result is recorded faithfully — so Claims Success, Billing Infrastructure, and the appointment lifecycle all operate against the same source of truth.

Your team owns the machinery that turns upstream decisions on where, when and how we file claims decisions into reliable, interpretable, recorded outcomes, measured against a clear north star: the percentage of appointments with a submittable primary claim that receive a conclusive payer response within 90 days. This is infrastructure the rest of the company runs on — and it's about to matter even more. Headway is building Project Switchboard, a single, authoritative financial state machine for every appointment. In that world, the claims lifecycle is triggered cleanly by upstream billing state, the claims state machine is the master of the claim's world, and results flow back only when appropriate. As we scale and move toward automated and agentic workflows, the reliability and correctness of the Claims Platform is what keeps money moving accurately for patients, providers, and payers.

You'll lead this engineering team end-to-end, co-own the roadmap with your PM, and report to a senior manager who will give you the autonomy to run your team while being a close thought partner. We're a technical engineering org — managers here lead through credibility in design reviews and active code contributions, not through distance from the work.

Responsibilities

• Lead an engineering team — hiring to a high bar, growing the people on it, and setting the culture your team operates by.
• Own the Claims Platform surface — a system other Headway teams depend on, and a roadmap you co-own with your product partner. That surface includes:
  • the claims lifecycle and status model,
  • the APIs to file and refile claims,
  • clearinghouse response processing (835 remittance parsing, 277 claim statuses, RARC/CARC handling),
  • claims interpretation (issue types/subtypes, ERA confidence evaluation),
  • the claim stack (claim-to-appointment aggregation, including multiple claims per appointment), and
  • integration with invoices.
• Set technical direction — architectural decisions, build-vs-buy trade-offs, reliability targets, and the standard the team operates to. Near-term this includes:
  • migrating ERA processing from Celery onto Temporal,
  • defining and committing to SLAs that center on the platform's core function,
  • improving analysis of low-confidence ERAs,
  • auditing CPI matching logic, and
  • guiding the deprecation of reverse ETL for secondary insurance.
• Partner cross-functionally — working with leaders across the insurance group (benefits, eligibility, corrections) and adjacent groups (Claims Success, Billing Infrastructure, patient billing, payer partnerships, data platform) to keep the whole system coherent — including the explicit, guardrailed handoffs Project Switchboard depends on.
• Maintain operational health — incident response, on-call sustainability, and the planning rhythm that lets your team ship predictably through high-stakes moments. The failure modes here are real and expensive: when systems diverge on a claim's financial state, the result is mis-paid providers, mis-billed patients, and audit-flagging discrepancies.

Requirements

• 3–5+ years of experience as a Software Engineer, with a background as a builder. You're comfortable in a design review, you read PRs when it matters, and your team trusts your technical read.
• 2+ years of experience managing engineers — whether as a tech lead with a handful of reports stepping into a bigger scope, or as a manager who has already run an engineering team through a scaling moment.
• Experience building systems other teams depended on — services, APIs, pipelines, or third-party integrations — at meaningful scale.
• Clear thinking about failure modes and treating reliability as a feature, not an afterthought.
• Experience building intelligent systems with the right leverage — comfortable evaluating where automation, prediction, or AI belongs, and where it doesn't.
• Ability to give direct, kind feedback. You've told someone a hard truth and left the relationship stronger for it.
• Energized by mission-driven work. You see how better insurance infrastructure is better access to mental health care.

Nice to Have

• Healthcare, insurance, claims, or payments platform experience — especially revenue cycle, EDI / X12 (837, 835, 277), clearinghouse integrations (e.g. Stedi), ERAs, or RARC/CARC handling.
• Experience with workflow orchestration (Temporal or similar) and migrating high-volume live pipelines off legacy async processing.
• Experience partnering closely with operations or support teams to build tooling that scales human work.
• Production ML or data-platform fluency — enough to evaluate, challenge, and partner credibly.
• Scaleup experience, Series B through D.

We expect our engineering managers to remain active technical contributors — pairing with engineers, driving key design decisions, and personally owning select deliverables. You'll lead through doing, not just directing.

Pay

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.

Benefits

• 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