Senior Engineering Manager (Infrastructure)

ABOUT ENGINEERING AT HEADWAY

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide. The engineering team at Headway is a small but mighty team using technology to build that future (and have a fun time while doing it!).

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.

As AI dramatically increases code velocity across the org, our mandate is to make every change safe from the start and build systems that get safer as they get faster, working toward a model where routine infrastructure is self-serve and the team spends the majority of its time on strategic platform work. That means owning the reliability, performance, and scalability of Mamba, Headway's FastAPI/Python monolith, and the AWS infrastructure it runs on. This is a technical leadership role: you'll set strategy and vision for the team, report to the Head of Engineering Foundations, and lead through credibility in design reviews and incident response, not through distance from the work.

An engineering team: hiring to a high bar into a growing team, developing engineers through the senior and staff levels, and running an effective on-call rotation for a team the rest of engineering depends on.

The infrastructure platform: a system every other Headway team builds on, and a roadmap spanning cloud infrastructure, deployment pipelines, LLM infrastructure, the data layer, and observability.

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