Lead the Infrastructure team at a Series D healthtech company, owning cloud infrastructure, LLM systems, and platform reliability while building and managing a high-performance engineering team.
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 75,000 providers across all 50 states run their practice on our software, serving over 1 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. 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!).
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
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.
Sourced from the a16z Speedrun talent network — apply on Speedrun.