Senior Engineering Manager (Infrastructure)
Company Overview
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. We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.).
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.
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.
- 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.
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.
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.
Experience We're Seeking
- 5-7+ years of experience as an Engineering Manager, 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.
- 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.
- 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.
Preferred Qualifications
- 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.
Salary & Benefits
We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically.
Location
New York City; San Francisco, CA; Seattle, WA (Hybrid)
Equal Opportunity Statement
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.
How to Apply
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.
