Senior Engineering Manager

Responsibilities

• Lead the Infrastructure team within Engineering Foundations, partnering with Agentic Engineering and Eddy, Headway’s internal AI platform.
• Hire, develop, and retain engineers through senior and staff levels while running an effective on-call rotation.
• Own the infrastructure platform roadmap across cloud infrastructure, deployment pipelines, LLM infrastructure, the database layer, and observability.
• Drive a shift from reactive support toward self-service infrastructure and strategic platform work.
• Lead architectural and deployment validation efforts to reduce incident blast radius and duration.
• Define production-readiness expectations for AI workloads.
• Co-own container security and secrets management with the Security team.
• Make the platform accessible and understandable to product engineering teams.
• Set strategy and vision, establish measurable infrastructure goals, and communicate foundational investment needs to senior leadership.
• Maintain the reliability, performance, and scalability of Mamba, Headway’s FastAPI/Python monolith, and its AWS infrastructure.
• Participate in design reviews, incident response, and postmortems.

Requirements

• 5–7+ years of experience as an Engineering Manager, including experience leading infrastructure or platform teams.
• 5+ years of experience as a Software or Infrastructure Engineer.
• 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 competing demands including support queues, strategic roadmaps, on-call rotations, and external dependencies.
• Familiarity with cloud infrastructure at scale, particularly AWS.
• Experience with observability tooling such as Datadog.
• Experience with deployment pipelines in environments where reliability is a product requirement.
• Experience owning platform strategy and representing it to senior leadership.

Nice-to-haves

• Experience leading 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.

Compensation and Benefits

• Annual salary range: $265,200–$331,500.
• Headway is committed to providing reasonable accommodations for qualified individuals with disabilities.