Staff Infrastructure Engineer

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Headway

501 - 1000 employees

Founded 2019

🏥 Healthcare

🏪 Marketplace

☁️ SaaS

💰 $100M Series D - Headway on 2024-07

Healthcare • Marketplace • SaaS

Headway is a healthcare technology company (Therapymatch, Inc. ) that operates an insurance-native marketplace connecting people with licensed mental health providers — therapists and psychiatrists — for in-person and online care. Headway matches users with providers by specialty, location, and insurance coverage, handles insurance verification and billing, and offers tools for providers (provider portal and an insurance-native EHR) to reduce administrative burden. The platform partners with 100+ insurance plans, supports many languages, and emphasizes affordable, in-network mental health care.

📋 Description

• Architect and own the cloud platform used by every Headway engineer • Redesign deployment architecture to isolate failures and contain blast radius • Own the ECS and EKS container footprint and evaluate broader EKS adoption for AI workloads • Design the next iteration of inter-service network connectivity • Own capacity engineering for spiky workloads and improve autoscaling reliability • Build a Terraform self-serve infrastructure platform with guardrails • Establish per-team cost attribution across AWS, Datadog, and LLM spend • Own Python monolith runtime performance, including garbage collection, event loop contention, and runtime limits • Lead framework and package upgrades • Provide technical direction through architecture reviews, runbooks, and paved-road tooling • Drive infrastructure decisions across team boundaries and raise the infrastructure engineering bar organization-wide

🎯 Requirements

• 8 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 infrastructure platforms for other engineering teams • Hands-on autoscaling and capacity engineering experience • Container orchestration experience with ECS and/or EKS • Track record making deployments safe and self-serve for other teams • Staff-level influence across team boundaries without requiring management authority • FinOps and cloud cost optimization experience is a nice-to-have • Kubernetes and EKS depth is a nice-to-have • Observability tooling at scale, including Datadog, is a nice-to-have • Experience in healthcare or other regulated environments is a nice-to-have • Experience with event-driven systems is a nice-to-have • Authorization to work in the United States • Willingness or ability to address employment visa sponsorship requirements

🏖️ Benefits

• Comprehensive and competitive total rewards package • Robust health and wellness benefits • Retirement savings • Meaningful ownership opportunities through equity • Reasonable accommodations for persons with disabilities

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