IT Engineer

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 carrying an escalation rotation, including occasional after-hours or event-day support for All Hands and office moves.

• Have fluency in a cloud-managed network stack — Meraki or equivalent — including wireless, VLANs, access points, and multi-ISP failover, with opinions about how to design for resilience.

• Want to deepen domain ownership of conference room AV at scale, ideally Zoom Rooms and Neat, including support for large hybrid all-hands, office relocations, and expansions.

• Have hands-on administration experience across several of the following: Okta, Google Workspace, Zoom, Slack, Jira Service Management, and 1Password, plus a strong understanding of macOS, Windows, and ChromeOS.

• Have experience with cross-functional partnership to ship office technology changes — in our case, with Workplace Experience, Security, and Employee Experience.

• Reach for workflow automation as a multiplier on your own work and care about verifying what it produces before it touches production.

• Think about blast radius before rolling out a change, validate by prototyping first, and turn what you fix into runbooks the rest of the team can run.

• Bonus points for experience with procurement processes.

*Must be based within commuting distance to New York City and able to work on-site two days per week, with flexibility for additional on-site support as needed, and able to travel to our other offices quarterly or as required.

Tools we use:

• Identity and access: Okta, 1Password

• Collaboration: Google Workspace, Slack, Zoom

• Service management: Jira Service Management

• Network: Meraki

• Conference room AV: Zoom Rooms, Neat

• Endpoints: macOS, Windows, ChromeOS

• Automation and AI: Tines, Claude, Glean

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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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 . 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 @ 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.