Infrastructure Engineer

Salary: $198,000 - 238,000 per year Requirements:

• We are looking for 8+ years of experience in platform, infrastructure, or SRE roles at companies with meaningful production traffic
• We need deep AWS expertise and hands-on ownership of compute and networking at scale, including ECS, EKS, RDS, networking, and IAM
• We value strong infrastructure-as-code experience, especially with Terraform, including building self-serve systems for other engineering teams
• We expect practical experience with autoscaling, capacity planning, and container orchestration using ECS and/or EKS
• We want a proven track record of making deployments safe and self-service for other teams, not only your own
• We seek Staff-level influence, with the ability to drive cross-functional decisions and lift the infrastructure bar across the organization without formal authority
• Nice to have: FinOps and cloud cost optimization experience
• Nice to have: strong Kubernetes and EKS depth
• Nice to have: observability tooling experience at scale, especially Datadog
• Nice to have: experience in healthcare or other regulated environments
• Nice to have: experience with event-driven systems

• We will rely on you to architect and own our cloud platform so every engineer can deploy on it
• We need you to make deployments routine, scaling automated, infrastructure self-service, and costs attributable
• You will redesign deployment architecture to contain blast radius so failures in one area do not impact others
• You will continue our move toward per-service deployment isolation and functional-area slices that limit failure propagation
• You will own our ECS and EKS footprint, evaluate broader EKS adoption for AI workloads, and design the next iteration of service-to-service networking
• You will take ownership of capacity planning for spiky workloads, using data-driven floors and early drift detection
• You will build a self-serve Terraform platform with guardrails so teams can manage standard infrastructure changes independently
• You will establish per-team cloud cost attribution across AWS, Datadog, and LLM spend so teams can make better tradeoffs
• You will own Python runtime and dependency health for our monolith, including garbage collection, event loop contention, and package upgrades
• You will serve as the technical anchor for our compute, networking, and deployment platform
• You will lead work that isolates blast radius, improves autoscaling reliability, and reduces routine operational burden for Infrastructure Engineering
• You will strengthen the engineering baseline through architecture reviews, runbooks, and paved-road tooling

• AI
• AWS
• Architect
• Cloud
• Datadog
• IAM
• Kubernetes
• LLM
• Python
• REST
• Spark
• Terraform
• DevOps
• FastAPI
• Network

More:

We are Headway, and our mission is to make mental healthcare accessible by removing the insurance and administrative barriers that keep therapy out of reach for many people. Our platform supports over 75,000 providers across all 50 states and serves more than 1 million patients. We are a Series D company backed by investors including a16z, Accel, and Spark Capital, with more than $325M in funding. Our Infrastructure Engineering team sits within Engineering Foundations alongside Agentic Engineering and Eddy, our internal AI platform. We provide the paved road for the rest of engineering, covering databases, deploys, asynchronous infrastructure, observability, autoscaling, and self-serve compute on AWS. We are committed to inclusion, reasonable accommodations for qualified individuals with disabilities, and building a team that reflects the diversity of the communities we serve.

last updated 33 week of 2026