H
Headway
Senior Software Engineer (Infrastructure)
Skills
PythonDatadogAIAWSKubernetesTerraform
15 days ago
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Important information
Contract type:
Permanent
Salary:
$182,750 – $278,500 / year
Location:
United States
Work mode:
Onsite
Published on:
10 October 2026
What they need
- Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide
- Infrastructure Engineering is one of three teams in Engineering Foundations, alongside Agentic Engineering and Eddy, Headway’s internal AI platform
- We own the infrastructure Headway runs on, as well as the performance and scalability of Headway’s FastAPI/Python monolith, and the AWS infrastructure it runs on
- We are the paved road the rest of engineering builds on: databases, deploys, asynchronous platform, observability, autoscaling, and self-serve compute infrastructure
- As AI dramatically increases code velocity across the org, our mandate is to make every change safe from the start and build systems that get safer as they get faster
- You will be on the Infrastructure team, which owns the cloud platform Headway runs on
- You will be the senior engineer driving work to isolate blast radius, make autoscaling trustworthy, and build a self-serve infrastructure platform so that the Infrastructure Engineering team focuses on the strategic and unusual, not the routine
- Deployment architecture and blast-radius containment. Redesign deployment so that a mistake in one part of our service cannot block or take down others. Continue to drive our shift toward per-service deploy isolation and functional-area slices that contain failures rather than propagating them across the platform
- 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: 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. Make infrastructure costs visible and attributable so teams can make informed tradeoffs
- Python runtime and dependency health. Own how the monolith behaves under load: garbage collection, event loop contention, and the runtime limits that bite first. Lead the framework and package upgrades most teams defer- You thrive in ambiguity, operate with a high degree of ownership, and are as comfortable setting technical direction as you are building
- You make other engineers better through architecture reviews, runbooks, and paved-road tooling that raises the baseline for everyone who ships on the platform
- A senior engineer who combines deep cloud and infrastructure expertise with the instincts to drive alignment across teams
- 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
- Track record making deploys safe and self-serve for other teams, not just your own
- 5 or more years in platform, infrastructure, or SRE roles at companies running significant production traffic
- Hands-on autoscaling and capacity engineering, and container orchestration with ECS and/or EKS
- Kubernetes and EKS depth
- FinOps and cloud cost optimization experience
- Experience in healthcare or other regulated environments
- Observability tooling at scale (Datadog)
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