Staff Infrastructure Engineer

Stack

Responsibilities

• ▹Deployment architecture and blast-radius containment: redesign deployment so that a mistake in one part of the service cannot block or take down others, continuing the shift toward per-service deploy isolation and functional-area slices
• ▹Container footprint and networking: own the ECS and EKS footprint, evaluate broader EKS adoption for AI workloads and design the next iteration of inter-service network connectivity
• ▹Capacity and scaling: own capacity for a spiky workload, with floors computed ahead of demand rather than chased by reactive scaling, self-deriving from data, with drift caught early
• ▹Self-serve infrastructure platform: build the Terraform self-serve platform with guardrails so engineering teams own their standard infrastructure changes and Reliability Engineering reviews only the non-standard ones
• ▹Cloud cost attribution and controls: stand up per-team cost attribution across AWS, Datadog and LLM spend, making infrastructure costs visible and attributable
• ▹Python runtime and dependency health: own how the monolith behaves under load (garbage collection, event loop contention, runtime limits) and lead the framework and package upgrades most teams defer

Requirements

• ▹8 or more years in platform, infrastructure or SRE roles at companies running significant production traffic
• ▹Deep AWS expertise and production ownership of compute and networking at scale (ECS, EKS, RDS, networking, IAM)
• ▹Strong infrastructure-as-code experience, particularly Terraform, including designing self-serve platforms for other engineering teams
• ▹Hands-on autoscaling and capacity engineering, and container orchestration with ECS and/or EKS
• ▹Track record making deploys safe and self-serve for other teams, not just your own
• ▹Staff-level influence: you drive decisions across team boundaries and raise the infrastructure bar org-wide without requiring management authority

Nice to have

• ▹FinOps and cloud cost optimization experience
• ▹Kubernetes and EKS depth
• ▹Observability tooling at scale (Datadog)
• ▹Experience in healthcare or other regulated environments
• ▹Experience with event driven systems

Soft skills

About the company

Headway is building a more accessible mental healthcare system in the US: it automates insurance administration, and over 75,000 providers run their practice on its software, serving over 1 million patients. A Series D company with $325M+ in funding.