About the role

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 IT Engineering at Headway Building a new mental healthcare system at Headway is only possible because of the scale and leverage that technology provides. The IT Engineering team is an essential function that builds operational efficiency into everything we do, giving our organization the tools needed to achieve our goals of reshaping mental healthcare. We own the identity, devices, business systems, and office technology that every Headwegian relies on, and we're expanding as Headway scales. About this role This is a role for someone who wants to be the person teammates escalate to and who wants to own a technical domain while doing it. About half your time is the escalation end of our support queue: the tickets the service desk hands up, which you resolve or triage yourself, plus the systemic patterns underneath them that are worth fixing for good. The rest is your own domain — the network and conference room AV across our three offices. That means owning the network health standard IT reports on company-wide, from proactive alerting to internet failover with no single point of failure, and owning the technology side of office-related projects from design through cutover. You'll move between people and systems all week, and the best version of this job turns what you learn helping people into the automation, monitoring, and runbooks that mean fewer people need help at all. You'll love this role if you want to: - Own the escalation end of the support queue, taking what's escalated from the service desk to resolve or triage, and identifying systemic patterns for the IT Engineering team to design permanent solutions for. - Own a technical domain of your own: networking and conference room AV across three offices. - Own the metric, not just the tickets. The office network health standard IT reports company-wide is yours: proactive alerting in every office, internet failover with no single point of failure, and network hygiene held at zero aging issues. - Do work people feel. A meeting that starts on time, WiFi nobody has to think about — invisible when it's right, and impossible to miss when it isn't. - Split your time between people and systems. You'll help Headwegians directly, then turn what you learn from them into the automation, monitoring, and documentation that means fewer of them need help. - Use automation on real workflows rather than as a side project, and help decide how a team in a regulated environment does that safely. - Grow with a function that's scaling. IT Operations is expanding as Headway does, and the standards you set now are the ones the team will run on. You'll be a good fit if you: - Have 3+ years of experience in IT at a distributed company, with a track record of resolving complex issues independently and being the person teammates escalate to. - Are comfortable ca