Senior Engineering Manager, Billing Platform Orchestration

Headway; New York (NY); Hybrid; USD 265,000 - 332,000; Full time

Benefits offered by this job

Equity compensation

Medical, Dental, and Vision coverage

HSA / FSA

401K

Work-from-Home Stipend

Therapy Reimbursement

16-week parental leave

Carrot Fertility annual reimbursement

13 paid holidays + holiday break

Flexible PTO

EAP

Job summary

Headway seeks a Senior Engineering Manager to own the Billing System platform and drive a new orchestration layer for the financial lifecycle of appointments. You will define state-machine design, guardrails, and scalable workflows, partnering with Finance to ensure the company’s financial records are accurate and auditable.

You’ll lead platform work across multiple teams, set technical direction, and guide the governance around when actions are allowed, backed by a track record in reliability

Qualifications

• 5+ years of experience as an Engineering Manager leading platform/infrastructure teams
• 5–7+ years of experience as a Software Engineer in backend and distributed systems
• Experience building or governing financial-grade systems (billing/payments/ledgers)
• Experience partnering with Finance, Accounting or compliance teams
• Strong prioritization and roadmap judgment for cross-team migrations

Responsibilities

• Own the technical strategy for the Billing System platform and its next chapter
• Define and guide a new orchestration layer and codified state machine for financial actions
• Build guardrail APIs, automated remittance ingestion, refunds and recoups
• Collaborate with Finance and Accounting to align outputs with financial records
• Provide governance for when every financial action can occur across 1.5M+ appointments per month

Skills

Engineering Leadership

Backend & Distributed Systems

Platform Governance

State Machines

Workflow Orchestration

Cross‑Team Collaboration

Data Integrity & Financial Correctness

Roadmap Prioritization

Security & Compliance Awareness

Job description

Headway seeks a Senior Engineering Manager to own the Billing System platform and drive a new orchestration layer for the financial lifecycle of appointments. You will define state-machine design, guardrails, and scalable workflows, partnering with Finance to ensure the company’s financial records are accurate and auditable.

You’ll lead platform work across multiple teams, set technical direction, and guide the governance around when actions are allowed, backed by a track record in reliability