Senior Engineering Manager – Infrastructure

🕒 October 17

🇺🇸 United States – Remote

💵 $265.2k - $331.5k / year

⏰ Full Time

🟠 Senior

👮‍♀️ Software Engineering Manager

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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

• Lead the Infrastructure team within Engineering Foundations • Own cloud infrastructure, deployment pipelines, LLM infrastructure, database platform, observability, and incident response • Hire and develop engineers through senior and staff levels • Run an effective on-call rotation • Set team strategy and vision • Own the reliability, performance, and scalability of Mamba, Headway’s FastAPI/Python monolith, and its AWS infrastructure • Drive the transition toward self-serve infrastructure and strategic platform work • Lead architectural and deployment validation to reduce incident blast radius • Define production-readiness expectations for AI workloads • Co-own container security and secrets management with the Security team • Make the platform accessible and understandable to product engineering teams • Report to the Head of Engineering Foundations • Collaborate with Engineering Leadership, Security, and product engineering teams

🎯 Requirements

• 5–7+ years of engineering leadership experience, including experience leading infrastructure or platform teams • 5+ years of experience as a Software or Infrastructure Engineer • Experience leading the shift from an infrastructure-owned-everything model to a self-serve platform • Experience managing the interface between platform and product engineering teams, including ownership boundaries and self-serve tooling • Ability to manage support queues, strategic roadmaps, on-call rotations, and external dependencies • Familiarity with AWS infrastructure at scale • Familiarity with Datadog or similar observability tooling • Familiarity with deployment pipelines at companies where reliability is a product requirement • Hands-on daily experience with AI coding tools • Successful completion of a hands-on AI coding interview • Experience owning platform strategy and presenting it to senior leadership • Experience leading significant architectural transitions • Experience building or governing LLM infrastructure and AI platform primitives • Experience in healthcare or another regulated environment is helpful

🏖️ Benefits

• Robust health and wellness benefits • Retirement savings • Meaningful ownership opportunities through equity • Reasonable accommodations for persons with disabilities

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