Senior Engineering Manager (Infrastructure)

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 90,000 providers across all 50 states run their practice on our software, serving over 2.6 million patients. 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, and building much of it with AI. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.

About Engineering at Headway

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide. The engineering team at Headway is a small but mighty team using technology to build that future (and have a fun time while doing it!).

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.

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