Senior Engineering Manager (Infrastructure)

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 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.

Responsibilities

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; The shift from reactive to strategic: driving the team's operating model toward self-serve infrastructure, so the team spends more time on strategic platform work and less on routine support requests; Blast-radius reduction: leading the architectural and deployment validation work that contains the scope and duration of incidents when they happen; The org interface: defining production readiness expectations for AI workloads, co-owning container security and secrets management with the Security team, and making sure the platform is accessible and well-understood by the product engineering teams that depend on it

Requirements

Experienced engineering team leader and people manager who is relationship-obsessed, drives results, and enables their teams to build for technical excellence; 5-7+ years of experience as an Engineering Manager, with experience leading infrastructure or platform teams; 5+ years of experience as a Software or Infrastructure Engineer, with enough depth to lead credibly in design reviews and incident response; Experience managing the interface between a platform team and the product engineering teams that depend on it, including setting ownership boundaries and building self-serve tooling; Comfortable managing through competing demands: a support queue, a strategic roadmap, an on-call rotation, and fast-moving external dependencies all at once; Familiarity with cloud infrastructure at scale (AWS), observability tooling (Datadog or similar), and deployment pipelines at companies where reliability is a product requirement; Experience owning a platform strategy and representing it to senior leadership: setting measurable goals for infrastructure work, and making the case for foundational investment in terms the business understands

Nice to have

Led a team through a significant architectural transition, such as moving from a monolith toward service isolation, or from manual to automated operations; Experience building or governing LLM infrastructure and AI platform primitives; Experience in healthcare or another regulated environment