Senior Software Engineer – Infrastructure

Headway

. Architect and own the cloud platform used by every Headway engineer .

Posted 10/2/2026full-timeRemote • United StatesSenior💰 $182,750 - $278,500 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates extensive expertise in AWS infrastructure management, including ECS and EKS, with a focus on building self-serve platforms and optimizing cloud costs. Proven ability to lead architectural improvements and enhance team capabilities through effective tooling and reviews.

Highest-signal resume keywords

AWS ExpertiseInfrastructure-As-Code (Terraform)Container Orchestration (ECS, EKS)Capacity EngineeringObservability Tooling (Datadog)

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Cloud ArchitectureDeployment ArchitecturePredictive Capacity ManagementPython Runtime OptimizationAutoscalingSelf-Serve Platform DesignEvent Loop Contention ManagementGarbage Collection ManagementCost AttributionTechnical Direction

Soft Skills

LeadershipCollaborationCommunication

Tools & Technologies

TerraformAWSDatadogECSEKSRDS

Industry Keywords

HealthcareRegulated EnvironmentsFinOpsCloud Cost Optimization

Tech Stack

Tools & technologies

AWSCloudKubernetesPythonTerraform

About the role

Key responsibilities & impact

Architect and own the cloud platform used by every Headway engineer
Redesign deployment architecture for per-service deploy isolation and functional-area blast-radius containment
Own the ECS and EKS footprint, evaluate broader EKS adoption for AI workloads, and design inter-service network connectivity
Own capacity for spiky workloads using predictive floors and early drift detection
Build a Terraform self-serve infrastructure platform with guardrails
Enable engineering teams to own standard infrastructure changes while Reliability Engineering reviews non-standard changes
Establish per-team cost attribution across AWS, Datadog, and LLM spend
Make infrastructure costs visible and attributable for informed tradeoffs
Own Python monolith runtime behavior under load, including garbage collection, event loop contention, and runtime limits
Lead framework and package upgrades
Drive technical direction and improve other engineers through architecture reviews, runbooks, and paved-road tooling

Requirements

What you’ll need

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, including ECS, EKS, RDS, networking, and IAM
Strong infrastructure-as-code experience, particularly Terraform
Experience designing self-serve platforms for other engineering teams
Hands-on autoscaling and capacity engineering
Container orchestration with ECS and/or EKS
Track record making deploys safe and self-serve for other teams
FinOps and cloud cost optimization experience (nice to have)
Kubernetes and EKS depth (nice to have)
Observability tooling at scale, including Datadog (nice to have)
Experience in healthcare or other regulated environments (nice to have)
Authorization to work in the United States for any employer
Must answer whether visa sponsorship will be required now or in the future

Benefits

Comp & perks

Equity / meaningful ownership opportunities
Robust health and wellness benefits
Retirement savings
Reasonable accommodations for persons with disabilities
Comprehensive and competitive total rewards package