Senior Software Engineer - Infrastructure

Headway

5d•$182,750 - $278,500

About The Position

Headway's mission is to fix the mental healthcare system by making it accessible to everyone. They have automated the administrative work involved in insurance, such as credentialing, claims, and payment reconciliation. Over 75,000 providers use their software, serving over 1 million patients. Headway is building tools for therapists, improving the process of finding a therapist, and investing in platform foundations for scalability. They are a Series D company with significant funding, seeking exceptional individuals to help achieve their mission and make this the most meaningful career experience for their employees.

Requirements

5 or more years in platform, infrastructure, or SRE roles at companies running significant production traffic
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
Hands-on autoscaling and 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
Ability to combine deep cloud and infrastructure expertise with the instincts to drive alignment across teams
Thrive in ambiguity, operate with a high degree of ownership, and be comfortable setting technical direction as well as building
Make other engineers better through architecture reviews, runbooks, and paved-road tooling

Nice To Haves

FinOps and cloud cost optimization experience
Kubernetes and EKS depth
Observability tooling at scale (Datadog)
Experience in healthcare or other regulated environments

Responsibilities

Architect and own the cloud platform that every engineer at Headway deploys on.
Make deploys boring, scaling automatic, infrastructure self-serve, and cost attributable.
Drive work to isolate blast radius, make autoscaling trustworthy, and build a self-serve infrastructure platform.
Redesign deployment architecture for per-service deploy isolation and functional-area slices to contain failures.
Own the ECS and EKS footprint, evaluate broader EKS adoption for AI workloads, and design the next iteration of inter-service network connectivity.
Own capacity for a spiky workload, ensuring floors are computed ahead of demand and self-deriving from data with early drift detection.
Build the Terraform self-serve platform with guardrails so engineering teams own their standard infrastructure changes.
Stand up per-team cost attribution across AWS, Datadog, and LLM spend.
Own how the monolith behaves under load, including garbage collection, event loop contention, and runtime limits.
Lead framework and package upgrades for the monolith.