Senior Software Engineer – Infrastructure

🔥 2 minutes ago

🇺🇸 United States – Remote

💵 $182.8k - $278.5k / year

⏰ Full Time

🟠 Senior

👷 Infrastructure Engineer

👻 Ghost score 0%

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Logo of Headway

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 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

• 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

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

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