Headway
Senior Software Engineer - Infrastructure
$183K–$278K
Remote · Remote · Senior · Full-time · Posted Oct 2, 2026
- Experience
- 5 or more years in platform, infrastructure, or SRE roles at companies running significant production traffic.
About the job
Architect and operate Headway’s cloud platform, improving deployment safety, scaling, self-service infrastructure, and cost visibility.
What you'll do
- Redesign deployments to isolate failures and reduce blast radius.
- Own container infrastructure, networking, capacity planning, and autoscaling across AWS.
- Build a Terraform self-service platform and improve cloud cost attribution and Python runtime health.
What they ask for
- Deep AWS expertise and production ownership of compute and networking at scale, including ECS, EKS, RDS, networking, and IAM.
- Strong infrastructure-as-code experience, particularly Terraform, including self-service platform design.
- Hands-on autoscaling, capacity engineering, and container orchestration with ECS and/or EKS.
- Track record making deployments safe and self-service for other teams.
Nice to have
- FinOps or cloud cost optimization experience; Kubernetes and EKS depth; or Datadog observability at scale.
- Experience in healthcare or other regulated environments.
Pay
$182,750 – $278,500 USD base salary
Tools
AWS, ECS, EKS, RDS, IAM, Terraform, Datadog, Python
AI focus
Evaluate broader EKS adoption for AI workloads and attribute LLM spend; the role also supports infrastructure safety as AI increases code velocity.
Model-written summary · the original posting is authoritative