Staff Infrastructure Engineer

Headway
San Francisco, Seattle, New York
Workplace: RemoteFull timeUSD 265,000 - 331,000 annuallyFunction: DevOps, Cloud & InfrastructureExperience: 8+ yearsSkills: ["Ownership","Technical leadership","Alignment","Architecture reviews","Runbook development"]

Own the cloud platform that powers every engineer’s deployments at scale. Drive safer deployment architecture with blast-radius containment, trustworthy autoscaling, and a self-serve infrastructure platform built on Terraform with guardrails. Lead compute, networking, and container orchestration across ECS/EKS, and make AWS and LLM spend attributable via cost controls. Improve runtime and dependency health for Headway’s FastAPI/Python monolith so changes ship safely and quickly.

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Headway
Headway
23 hours ago

Staff Infrastructure Engineer

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Source: Company careers pageValidated by: Fursa AI
Last checked: 12 hours agoStatus: Live

Job Summary

Own the cloud platform that powers every engineer’s deployments at scale. Drive safer deployment architecture with blast-radius containment, trustworthy autoscaling, and a self-serve infrastructure platform built on Terraform with guardrails. Lead compute, networking, and container orchestration across ECS/EKS, and make AWS and LLM spend attributable via cost controls. Improve runtime and dependency health for Headway’s FastAPI/Python monolith so changes ship safely and quickly.
Location: San Francisco, Seattle, New York
Workplace: Remote
Employment Type: Full time
Job Function: DevOps, Cloud & Infrastructure
Seniority: Mid level

Key Responsibilities

  • •Architect deployment processes and implement blast-radius containment so failures don’t propagate across the platform.
  • •Own container footprint and networking, including ECS/EKS footprint, inter-service connectivity, and evaluating broader EKS adoption for AI workloads.
  • •Drive capacity and scaling for spiky workloads using data-derived scaling and early drift detection.
  • •Build the Terraform self-serve infrastructure platform with guardrails so teams can manage standard changes with Reliability Engineering reviewing non-standard work.
  • •Implement cloud cost attribution across AWS, Datadog, and LLM spend; improve Python monolith runtime and dependency health under load.

Pay and Benefits

Salary: USD 265,000 - 331,000 annually

Key Requirements

  • •8+ years in platform, infrastructure, or SRE roles at companies running significant production traffic.
  • •Deep AWS expertise with production ownership across compute and networking (ECS, EKS, RDS, networking, IAM).
  • •Strong infrastructure-as-code experience, especially Terraform, including building self-serve platforms for other engineering teams.
  • •Hands-on experience with autoscaling/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.
Experience:8+ yearsCloud infrastructurePlatform engineeringSREProduction traffic
Skills:OwnershipTechnical leadershipAlignmentArchitecture reviewsRunbook development
Tech Stack:AWSECSEKSRDSIAMTerraformDatadogFastAPIPythonKubernetesLLMContainersAutoscaling

Company Brief

Headway
Headway is a technology-driven mental health platform that connects patients with licensed therapists and streamlines insurance-based mental healthcare access for providers and practices across the United States.
Industry: Mental Health
Company Size: Large (251 to 1,000 employees)
Growth: Scaleup
Headquarters: New York, United States
Founded: 2017
Website