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Headway

Senior Engineering Manager (Infrastructure)

US UTC-10 to UTC-5 $265k to $332k per year Full time Lead or Staff
Where you can live
Remote
Working hours
Overlap with UTC-10 to UTC-5
Salary
USD 265,200 to 331,500 per year
Posted
October 17, 2026
Python FastAPI AWS Spark LLMs Datadog

Summary from the posting

You'll lead the Infrastructure team , one of three teams in Engineering Foundations, alongside Agentic Engineering and Eddy, Headway's internal AI platform , that every other team at Headway builds on. You'll own cloud infrastructure, deployment pipelines, LLM infrastructure (gateway, multi-provider failover, per-team rate limiting), the database platform, observability, and incident response, while hiring and growing a high-performance team shipping at AI-accelerated velocity.

This is a short summary. The full description, requirements and the application form are on Headway's own career page.

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