The ad says“You have experience building or governing LLM infrastructure and AI platform primitives”
The ad says“Familiarity with cloud infrastructure at scale (AWS), observability tooling (Datadog or similar), and deployment pipelines at companies where reliability is a product requirement”
The ad says“5-7+ years of experience as an Engineering Manager, with experience leading infrastructure or platform teams”
The ad says“You are an infrastructure leader who is as comfortable in a postmortem as you are in a planning doc”
The ad says“You have experience building or governing LLM infrastructure and AI platform primitives”
Values
The ad says“Familiarity with cloud infrastructure at scale (AWS), observability tooling (Datadog or similar), and deployment pipelines at companies where reliability is a product requirement”
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
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
As a Senior Engineering Manager at Headway, you will work closely with Engineering Leadership, Security, and product engineering teams across the org to help shape the future of the engineering organization
Preferred experience
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
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
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
Comfortable managing through competing demands: a support queue, a strategic roadmap, an on-call rotation, and fast-moving external dependencies all at once
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
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
Familiarity with cloud infrastructure at scale (AWS), observability tooling (Datadog or similar), and deployment pipelines at companies where reliability is a product requirement
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
You have experience in healthcare or another regulated environment
You have experience building or governing LLM infrastructure and AI platform primitives
