Senior Engineering Manager (Infrastructure)

Headway as a Senior Engineering Manager (Infrastructure) and lead the Infrastructure team, which is essential for the success of all other engineering teams. You will own cloud infrastructure, deployment pipelines, LLM infrastructure, the database platform, observability, and incident response. This is a technical leadership role where you will set strategy and vision for the team, report to the Head of Engineering Foundations, and lead through credibility in design reviews and incident response.

About Headway

Comfortable managing through competing demands: a support queue, a strategic roadmap, an on-call rotation, and fast-moving external dependencies all at once

You've personally led the shift from "infra team owns everything" to a self-serve platform other engineers build on themselves — not just inherited or operated a system where that transition had already happened

You're personally hands-on with AI coding tools day to day — not just driving your team's AI adoption as a program. Every candidate goes through a hands-on AI coding interview as part of this loop

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

You are an infrastructure leader who is as comfortable in a postmortem as you are in a planning doc. You know how to run a team that carries a support queue while still making progress on strategic platform work. You hold the technical bar yourself and earn credibility with the team through the quality of your judgment, not your title

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

You have led a team through a significant architectural transition, such as moving from a monolith toward service isolation, or from manual to automated operations

Responsibilities

• You will also drive the team's operating model toward self-serve infrastructure and lead architectural and deployment validation work.
• Lead the Infrastructure team, overseeing cloud infrastructure, deployment pipelines, LLM infrastructure, and the database platform.
• Drive the team's operating model toward self-serve infrastructure, allowing the team to focus on strategic platform work.
• Set strategy and vision for the team, report to the Head of Engineering Foundations, and lead through credibility in design reviews and incident response.
• We're looking for experienced engineering team leaders and people managers who are relationship-obsessed, drive results, and enable their teams to build for technical excellence

Requirements

• 5+ years of experience as a Software or Infrastructure Engineer, with enough depth to lead credibly in design reviews and incident response
• 5-7+ years of experience of engineering leadership experience, with experience leading infrastructure or platform teams
• You have experience building or governing LLM infrastructure and AI platform primitives

Preferred

• You have experience in healthcare or another regulated environment

USD 265,200 - 331,500