Staff Infrastructure Engineer
Headway · Remote · Remote · San Francisco, CA · Seattle, WA · New York City ·
COMPENSATION
$265k – $331k
Listed on the employer's job board (Ashby)
- Staff level role
- Fully remote (US)
- AWS + Terraform
- Python + FastAPI
- Healthcare mission
Headway is building a new mental healthcare system by automating insurance administration and providing practice management tools. The Infrastructure Engineering team owns the platform foundations, including the FastAPI/Python monolith and AWS infrastructure, enabling scale for therapists and patients nationwide.
As a Staff Engineer, you will serve as the technical anchor for the compute and networking platform. You will drive initiatives to isolate blast radius, improve autoscaling reliability, and build a self-serve infrastructure platform that allows other teams to operate independently.
What you'll do
- Redesign deployment architecture to contain blast radius and prevent cross-service failures
- Own ECS and EKS footprint and design next-generation inter-service network connectivity
- Engineer capacity planning based on data rather than reactive scaling for spiky workloads
- Build a Terraform-based self-serve platform with guardrails for engineering teams
- Implement per-team cost attribution across AWS, Datadog, and LLM spend
- Optimize Python runtime performance including garbage collection and event loop contention
What you'll need
- 8+ years in platform, infrastructure, or SRE roles with significant production traffic
- Deep AWS expertise in compute, networking, ECS, EKS, RDS, and IAM at scale
- Strong experience with Terraform and designing self-serve infrastructure platforms
- Proven track record in hands-on autoscaling, capacity engineering, and container orchestration
- Experience making deployments safe and self-serve for multiple engineering teams
- Ability to drive technical decisions and influence across team boundaries at a staff level
Nice to have
- Experience with FinOps and cloud cost optimization strategies
- Deep knowledge of Kubernetes and EKS
- Proficiency with observability tooling at scale, specifically Datadog
- Background in healthcare or other highly regulated environments
- Experience working with event-driven systems
Stack
- AWS
- Terraform
- Python
- FastAPI
- ECS
- EKS
- Datadog
How you'll work
- Fully remote position within the United States
- Part of the Engineering Foundations team