Senior Software Engineer – Infrastructure

🕒 October 2

🇺🇸 United States – Remote

💵 $182.8k - $278.5k / year

⏰ Full Time

🟠 Senior

👷 Infrastructure Engineer

🦅 H1B Visa Sponsor

This company has sponsored H1B visas in the past.

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Headway

WebsiteLinkedInAll Job Openings

201 - 500 employees

Founded 2019

🛡️ Insurance

💼 Consulting

📦 Logistics

Insurance • Consulting • Logistics

Headway is a platform that connects individuals with mental health providers, helping them find the right fit according to their needs and insurance coverage. By partnering with numerous insurance providers, Headway ensures that users can access mental health care affordably. It offers both in-person and virtual care options, and manages the payment and billing processes for a hassle-free experience. The platform's aim is to simplify the search and access to therapy and psychiatric support for users, allowing them to focus on their mental health without the administrative burdens.

📋 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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