# Senior Engineering Manager, Billing Infrastructure at Headway

- Company: Headway
- What the company does: Backed by Accel, a16z and GV.
- Company website: https://headway.co/
- Type: Startups
- Level: Senior
- Location: New York City
- Work setup: On-site
- Pay: $265K to $332K base salary per year (USD)
- Posted: 2026-09-10
- Apply by: 2026-10-25
- Apply: https://jobs.ashbyhq.com/headway/748fe666-44a1-4509-af9f-6ce6c3252e12
- Page: https://www.1752.vc/careers/jobs/headway-senior-engineering-manager-billing-infrastructure/

## About 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 appointment’s financial lifecycle: explicit states, enforced guardrails, automated reconciliation, immutable explainability, and safe simulation of financial logic.

## What they're looking for

- 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’ve 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
- You’ve 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

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