Senior Software Engineer - Infrastructure

Location

Remote, United States

Employment Type

Full time

Compensation

• $182,750 – $278,500 • Offers Equity

About the Position

Headway’s mission is to fix the mental healthcare system by building a new system everyone can access. We've automated the administrative work, and now we're looking for exceptional people to help us achieve this mission. Join us, and help change mental healthcare for the better.

Responsibilities

• Deployment architecture and blast-radius containment. Redesign deployment so that a mistake in one part of our service cannot block or take down others. Continue to drive our shift toward per-service deploy isolation and functional-area slices that contain failures rather than propagating them across the platform.
• Container footprint and networking. Own the ECS and EKS footprint, evaluate broader EKS adoption for AI workloads, and design the next iteration of inter-service network connectivity.
• Capacity and scaling. Own capacity for a spiky workload: floors computed ahead of demand rather than chased by reactive scaling, self-deriving from data, with drift caught early.
• Self-serve infrastructure platform. Build the Terraform self-serve platform with guardrails so engineering teams own their standard infrastructure changes and Reliability Engineering reviews only the non-standard ones.
• Cloud cost attribution and controls. Stand up per-team cost attribution across AWS, Datadog, and LLM spend. Make infrastructure costs visible and attributable so teams can make informed tradeoffs.
• Python runtime and dependency health. Own how the monolith behaves under load: garbage collection, event loop contention, and the runtime limits that bite first. Lead the framework and package upgrades most teams defer.

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

Nice to Have

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

We Offer

• Competitive salary
• Equity options
• Comprehensive health and wellness benefits
• Retirement savings
• Professional development budget

About the Company

Headway is a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.). We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

Headway participates in E-Verify. To learn more, click here.

A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.