Senior Infrastructure Lead, AI Platform & Scale

Headway; United States; Remote; USD 180,000 - 280,000; Full time

Job summary

Headway is seeking an experienced engineering leader to head the Infrastructure team within Engineering Foundations in the US. You will own cloud infrastructure, deployment pipelines, LLM infrastructure, and observability, while growing a high-performance team shipping AI-accelerated work.

You will set strategy, partner with Security and product engineers, and drive a shift toward self-serve, reliable platform services that improve safety and speed across the organization.

Qualifications

• 5-7+ years of engineering leadership experience, incl. infrastructure or platform teams.
• 5+ years as Software or Infrastructure Engineer with design review/incident response depth.
• Experience moving to a self-serve platform model and defining ownership boundaries.

Responsibilities

• Lead and grow the infrastructure/platform team at Headway.
• Own cloud infrastructure, deployment pipelines, and LLM infrastructure.
• Define production readiness and container security with Security.
• Drive shift from reactive to strategic work and reduce blast radii.
• Set strategy and vision, report to Head of Engineering Foundations.

Skills

Engineering leadership

Infrastructure/platform leadership

AWS cloud infrastructure

Observability tooling

Deployment pipelines

AI coding tools

Platform strategy & leadership

Tools

AWS

Datadog

LLM infrastructure

CI/CD pipelines

Job description

Headway is seeking an experienced engineering leader to head the Infrastructure team within Engineering Foundations in the US. You will own cloud infrastructure, deployment pipelines, LLM infrastructure, and observability, while growing a high-performance team shipping AI-accelerated work.

You will set strategy, partner with Security and product engineers, and drive a shift toward self-serve, reliable platform services that improve safety and speed across the organization.