Engineering Manager (Claims)

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.

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.

An engineering team — hiring to a high bar, growing the people on it, and setting the culture your team operates by.

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.

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.

Cross-functional partnership — 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.

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. Your team is the one that keeps that from happening.

You have 3–5+ years of experience as a Software Engineer and came up as a builder. You're comfortable in a design review, you read PRs when it matters, and your team trusts your technical read.

You've managed engineers for 2+ years — 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.

You've built systems other teams depended on — services, APIs, pipelines, or third-party integrations — at meaningful scale. You think clearly about failure modes and treat reliability as a feature, not an afterthought.

You're a builder of intelligent systems with the right leverage — comfortable evaluating where automation, prediction, or AI belongs, and where it doesn't.

You give direct, kind feedback. You've told someone a hard truth and left the relationship stronger for it.

You're energized by mission-driven work. You see how better insurance infrastructure is better access to mental health care.

Bonus points for:

• 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.

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

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.