Senior Engineering Manager - Infrastructure & AI Platform

Headway; New York, Northern (NY, KY); Hybrid; USD 180,000 - 280,000; Full time

Job summary

Headway is seeking a Senior Engineering Manager to lead the Infrastructure team within Engineering Foundations. You will own cloud infrastructure, deployment pipelines, LLM infrastructure, and the data layer, while hiring and growing a high-performance team shipping with AI-accelerated velocity.

You will drive production readiness, security collaboration, and architectural validation to reduce blast radius, ensuring Headway's platforms remain reliable as the org scales its medical AI and therapy

Qualifications

• Proven leadership of infrastructure or platform teams.
• Experience in large-scale cloud environments (AWS).
• Track record of shipping reliable systems and improving velocity.
• Ability to balance on-call support with strategic work.
• Familiarity with AI/LLM infra and security considerations.

Responsibilities

• Lead the Infrastructure team within Engineering Foundations.
• Own cloud infrastructure, deployment pipelines, and LLM infra.
• Define production readiness and container security with Security.
• Shift the team from reactive to strategic, enabling self-serve infra.
• Oversee reliability, performance, and scalability of essential platforms.

Skills

Engineering management

Platform leadership

Cloud infrastructure

Observability tooling

LLM infrastructure

Team leadership

Strategic planning

Tools

AWS

Datadog

CI/CD pipelines

Job description

Headway is seeking a Senior Engineering Manager to lead the Infrastructure team within Engineering Foundations. You will own cloud infrastructure, deployment pipelines, LLM infrastructure, and the data layer, while hiring and growing a high-performance team shipping with AI-accelerated velocity.

You will drive production readiness, security collaboration, and architectural validation to reduce blast radius, ensuring Headway's platforms remain reliable as the org scales its medical AI and therapy