ABOUT THIS ROLE
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.
WHAT YOU'LL OWN
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.
PRINCIPLES THAT GUIDE US
Focus on the mission: We view software as a means of effecting change in the world, not as an end unto itself. We write software to empower our patients and therapist to better solve the problems they're facing.
Ship small, learn fast: We are building new and novel products and believe that we learn what our users need by quickly shipping and iteration
Everything is a product: Whether it's our patient search experience or a developer productivity improvement, we treat everything we build at Headway as a product with end-users in mind.
Optimize for trust: We believe that engineers should be continually learning. To learn effectively and to be productive, engineers must feel safe asking questions and discussing mistakes.
WHO YOU ARE
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. 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.
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.
5-7+ years of experience of engineering leadership experience, with experience leading infrastructure or platform teams.
5+ years of experience as a Software or Infrastructure Engineer, with enough depth to lead credibly in design reviews and incident response
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.
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
Comfortable managing through competing demands: a support queue, a strategic roadmap, an on-call rotation, and fast-moving external dependencies all at once
Familiarity with cloud infrastructure at scale (AWS), observability tooling (Datadog or similar), and deployment pipelines at companies where reliability is a product requirement.
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
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
Below are additional experiences we think help engineering managers succeed at Headway:
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
COMPREHENSIVE BENEFITS
Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave.
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. https://www.e-verify.gov/sites/default/files/everify/posters/EVerifyParticipationPoster.pdf
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 http://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.
