Senior Software Engineer - Infrastructure

The role

You will architect and own the cloud platform that every engineer at Headway deploys on. You will drive work to isolate blast radius, make autoscaling trustworthy, and build a self-serve infrastructure platform.

What you will do

• Redesign deployment for blast-radius containment and per-service deploy isolation.
• Own the ECS and EKS footprint and design inter-service network connectivity.
• Manage capacity and scaling for spiky workloads.
• Build a Terraform self-serve platform with guardrails.
• Stand up per-team cost attribution across AWS, Datadog, and LLM spend.
• Own Python runtime and dependency health for the monolith.
• Lead framework and package upgrades.
• Make other engineers better through architecture reviews, runbooks, and paved-road tooling.

Required qualifications

• 5 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

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

Benefits

• Medical
• dental
• vision
• HSA/FSA
• 401(k) including match for 2027!
• Carrot Fertility reimbursement
• paid parental, medical and caregiver leave

About the company

Headway is a Series D company building a new mental healthcare system. They provide software for over 90,000 providers to manage their practices and serve over 2.6 million patients.