Senior Engineering Manager (Infrastructure)

Headway•New York, NY

10h

About The Position

Headway's mission is to fix the mental healthcare system by building a new system that everyone can access. They have automated the administrative work of credentialing, claims, and payment reconciliation, and are building tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in platform foundations to enable this at scale. The engineering team uses technology to build this future, guided by principles of focusing on the mission, shipping small to learn fast, treating everything as a product, and optimizing for trust. This role will lead the Infrastructure team, which is responsible for cloud infrastructure, deployment pipelines, LLM infrastructure, the database platform, observability, and incident response. The goal is to make every change safe from the start and build systems that get safer as they get faster, moving towards self-serve routine infrastructure and allowing the team to focus on strategic platform work. This includes owning the reliability, performance, and scalability of Headway's FastAPI/Python monolith and its AWS infrastructure. It is a technical leadership role focused on strategy and vision, reporting to the Head of Engineering Foundations.

Requirements

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 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

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.
Owning the infrastructure platform, which includes cloud infrastructure, deployment pipelines, LLM infrastructure, the data layer, and observability.
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.
Leading the architectural and deployment validation work that contains the scope and duration of incidents when they happen.
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.