Senior Engineering Manager (Infrastructure)

Headway•New York, NY

2d•$265,200 - $331,500

About The Position

Headway is building a new mental healthcare system to make care accessible to everyone. We've automated the administrative work of insurance, and now over 75,000 providers use our software, serving over 1 million patients. We are developing tools for therapists, improving the process of finding a therapist, and investing in platform foundations for scale. We are a Series D company with significant funding, seeking exceptional individuals to help us achieve our mission and make this the most meaningful experience of their careers. The engineering team at Headway uses technology to build this future. Our guiding principles include focusing on the mission, shipping small to learn fast, treating everything as a product, and optimizing for trust by fostering a safe environment for learning and discussing mistakes.

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.
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

Lead the Infrastructure team, which is responsible for cloud infrastructure, deployment pipelines, LLM infrastructure, the database platform, observability, and incident response.
Hire and grow a high-performance team that ships at AI-accelerated velocity.
Make every change safe from the start and build systems that get safer as they get faster, moving towards self-serve routine infrastructure.
Own the reliability, performance, and scalability of Headway's FastAPI/Python monolith and its AWS infrastructure.
Set strategy and vision for the team, report to the Head of Engineering Foundations, and lead through credibility in design reviews and incident response.
Manage an engineering team, including hiring, developing engineers, and running an effective on-call rotation.
Own the infrastructure platform roadmap, spanning cloud infrastructure, deployment pipelines, LLM infrastructure, the data layer, and observability.
Drive the team's operating model towards self-serve infrastructure.
Lead architectural and deployment validation work to reduce the blast radius 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.