Senior Engineering Manager (Infrastructure) Headway
Therapist marketplace for insurance-covered mental healthcare.
Permanent
United States of America
Fully-remote
265,2K to 331,5K $ a year
> 5 years
Skills we're looking for
Cloud & infrastructure
Leadership
FastAPI
Datadog
AWS
+1
You'll be part of
United States of America
3246 employees
Our take
1 in 4 US citizens are currently living with treatable mental health conditions, however, a vast majority of people are unable to access the care they need, the primary reason being cost. Headway connects clients with therapists who accept insurance as payment and provides independent practitioners with the tools and resources needed to serve their patients and manage administrative workloads. Headway’s concept is timely, with national mental health under particular strain following events from the past few years. The company facilitates over 600,000 appointments per month and has attracted backing from the likes of Accel and Google Ventures. Covering 16 states and the District of Columbia, the company intends to broaden its presence across the US with over $325M in funding behind it. This is a crucial avenue for further growth, as medical care deserts across the US mean the potential market is vast.
You'll be working on
- You’ll lead the Infrastructure team — one of three teams in Engineering Foundations, alongside Agentic Engineering and Eddy, Headway’s internal AI platform — that every other team at Headway builds on
- You’ll own cloud infrastructure, deployment pipelines, LLM infrastructure (gateway, multi-provider failover, per-team rate limiting), the database platform, observability, and incident response, while hiring and growing a high-performance team shipping at AI-accelerated velocity
- As AI dramatically increases code velocity across the org, our mandate is to make every change safe from the start and build systems that get safer as they get faster, working toward a model where routine infrastructure is self-serve and the team spends the majority of its time on strategic platform work
- That means owning the reliability, performance, and scalability of Mamba, Headway’s FastAPI/Python monolith, and the AWS infrastructure it runs on. This is a technical leadership role: you’ll set strategy and vision for the team, report to the Head of Engineering Foundations, and lead through credibility in design reviews and incident response, not through distance from the work
- An engineering team: hiring to a high bar into a growing team, developing engineers through the senior and staff levels, and running an effective on-call rotation for a team the rest of engineering depends on
- The infrastructure platform: a system every other Headway team builds on, and a roadmap spanning cloud infrastructure, deployment pipelines, LLM infrastructure, the data layer, and observability
- The shift from reactive to strategic: driving the team’s operating model toward self-serve infrastructure, so the team spends more time on strategic platform work and less on routine support requests
- Blast-radius reduction: leading the architectural and deployment validation work that contains the scope and duration of incidents when they happen
- The org interface: defining production readiness expectations for AI workloads, co-owning container security and secrets management with the Security team, and making sure the platform is accessible and well-understood by the product engineering teams that depend on it
- As a Senior Engineering Manager at Headway, you will work closely with Engineering Leadership, Security, and product engineering teams across the org to help shape the future of the engineering organization
We're looking for
- We’re looking for experienced engineering team leaders and people managers who are relationship-obsessed, drive results, and enable their teams to build for technical excellence
- 5+ years of experience as a Software or Infrastructure Engineer, with enough depth to lead credibly in design reviews and incident response
- 5-7+ years of experience of engineering leadership experience, with experience leading infrastructure or platform teams
- Comfortable managing through competing demands: a support queue, a strategic roadmap, an on-call rotation, and fast-moving external dependencies all at once
- You’ve personally led the shift from “infra team owns everything” to a self-serve platform other engineers build on themselves — not just inherited or operated a system where that transition had already happened
- You’re personally hands-on with AI coding tools day to day — not just driving your team’s AI adoption as a program. Every candidate goes through a hands-on AI coding interview as part of this loop
- Familiarity with cloud infrastructure at scale (AWS), observability tooling (Datadog or similar), and deployment pipelines at companies where reliability is a product requirement
- Experience owning a platform strategy and representing it to senior leadership: setting measurable goals for infrastructure work, and making the case for foundational investment in terms the business understands
- You are an infrastructure leader who is as comfortable in a postmortem as you are in a planning doc. You know how to run a team that carries a support queue while still making progress on strategic platform work. You hold the technical bar yourself and earn credibility with the team through the quality of your judgment, not your title
- Experience managing the interface between a platform team and the product engineering teams that depend on it, including setting ownership boundaries and building self-serve tooling
- You have led a team through a significant architectural transition, such as moving from a monolith toward service isolation, or from manual to automated operations
- You have experience building or governing LLM infrastructure and AI platform primitives
- You have experience in healthcare or another regulated environment