IT Engineer, Endpoints

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.

Building a new mental healthcare system at Headway is only possible because of the scale and leverage that software can provide. The IT team at Headway is an essential function at Headway that builds operational efficiency into everything we do, giving our organization the tools needed to achieve our goals of reshaping mental healthcare. In this role, you’ll have the unique opportunity to be the builder and driver of our dedicated, in-house IT Engineering efforts. You will execute projects, both technically and organizationally, to tackle challenges as the company continues to rapidly scale.

You’ll love this role if you want to

• Own the full device lifecycle of every endpoint at Headway — from procurement and provisioning through retirement — across macOS, Windows, and ChromeOS.
• Build the foundation for device trust and BYOD programs in a HIPAA-regulated environment, partnering closely with Security to make sure the right person on the right device is accessing the right thing.
• Connect endpoint management with identity by automating the onboarding/offboarding flow end-to-end so that device, access, and entitlements move together as one motion
• Replace toil with automation — using AI, scripting, and iPaaS tools to eliminate the manual work that keeps endpoint teams reactive instead of proactive.
• Develop a clear point of view on choice programs, standard equipment, refresh cadence, and the financial discipline that comes with managing devices at scale to shape how Headway scales its endpoint fleet.
• Be the SME other teams come to for anything endpoint or device-related, while staying connected to users through a light, predictable on-call rotation.

You may be a good fit if you

• Have at least 3 years as a Client Platform / Endpoint / IT Systems Engineer, with deep hands-on experience managing macOS, Windows, and ChromeOS fleets at scale (ChromeOS is a plus).
• Are fluent in JAMF Pro, Microsoft Intune, and Google Chrome Enterprise Management, and have opinions about when to reach for each.
• Bring solid knowledge of IAM, you've built and maintained workflows, configured groups and policies, and understand how identity, access, and devices intersect
• Have scripted and automated your way out of repetitive work – comfortable with Bash, Python, or an iPaaS tool like Tray.io, Tines.
• Lean AI-forward actively experimenting with how AI can level up endpoint operations, from triage to remediation to documentation
• Are stakeholder-savvy and have partnered cross functionally to ship high impact endpoint changes such as OS patches, or large scale endpoint software deployments.
• Have built or operated BYOD programs, and endpoint security and compliance controls in a regulated environment — HIPAA, SOC 2, HITRUST, or similar — and can speak to device trust, attestation, and posture management.
• Are an excellent project manager, organized, methodical, comfortable owning a roadmap and reporting on impact with data.
• Are a team player with no ego who welcomes feedback and is adept at managing up and across.

Tools we use

• Identity and Access Management: Okta, Lumos
• Email and Messaging: Gmail and Slack
• Document Creation and Collaboration: Google Workspace, Confluence
• Credential Management: 1Password
• Ticketing: Jira Service Desk, ZenDesk, Jira Projects
• Project Planning: Jira
• Endpoint Management: JAMF, InTune, ChromeOS

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 https://headway.co/careers. 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 @findheadway.com 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.