Senior Engineering Manager (Infrastructure)

Headway

1d•$265,200 - $331,500

About The Position

Headway is seeking a Senior Engineering Manager to lead its Infrastructure team within Engineering Foundations. The team provides the platform that other engineering teams build on, and owns cloud infrastructure, deployment pipelines, LLM infrastructure, the database platform, observability, and incident response. The role includes setting team strategy and vision, hiring and developing engineers, and maintaining a high technical bar through hands-on involvement in design reviews and incident response. The position reports to the Head of Engineering Foundations. The manager will lead the reliability, performance, and scalability of Mamba, Headway’s FastAPI/Python monolith, and the AWS infrastructure it runs on. A key objective is to make infrastructure safer as AI increases development velocity, shift routine infrastructure work toward self-service, reduce incident blast radius, and enable the team to focus on strategic platform work. The role also partners with Engineering Leadership, Security, and product engineering teams on production readiness for AI workloads, container security, secrets management, and platform accessibility.

Requirements

5–7+ years of engineering leadership experience, including experience leading infrastructure or platform teams.
5+ years of experience as a Software or Infrastructure Engineer, with sufficient technical depth to lead design reviews and incident response credibly.
Personally led a transition from an infrastructure team that owns everything to a self-service platform used by other engineers.
Experience managing the interface between a platform team and dependent product engineering teams, including setting ownership boundaries and building self-service tooling.
Ability to manage a support queue, strategic roadmap, on-call rotation, and fast-moving external dependencies simultaneously.
Familiarity with AWS-scale cloud infrastructure, observability tooling such as Datadog or similar, and deployment pipelines in environments where reliability is a product requirement.
Hands-on use of AI coding tools in day-to-day work; candidates complete a hands-on AI coding interview.
Experience owning platform strategy and presenting it to senior leadership, including setting measurable infrastructure goals and making the business case for foundational investment.
Experienced engineering team leader and people manager who builds relationships, drives results, and enables technical excellence.

Nice To Haves

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.

Responsibilities

Hire engineers to a high bar and develop them through senior and staff levels.
Run an effective on-call rotation for a team that other engineering teams depend on.
Own the infrastructure platform and roadmap across cloud infrastructure, deployment pipelines, LLM infrastructure, the data layer, and observability.
Drive a shift toward self-service infrastructure and reduce routine support work so the team can focus on strategic platform initiatives.
Lead architectural and deployment validation work to reduce the scope and duration of incidents.
Define production readiness expectations for AI workloads.
Co-own container security and secrets management with the Security team.
Ensure the platform is accessible and well-understood by product engineering teams.
Set team strategy and vision, and represent platform strategy to senior leadership.
Set measurable goals for infrastructure work and explain the business case for foundational investment.
Lead through technical credibility in design reviews and incident response.
Manage competing demands across support requests, the strategic roadmap, on-call responsibilities, and external dependencies.