IT Engineer, Endpoints

· Remote

Location

Remote

Type

Full Time

Job Description

HeadwayJobs
IT Engineer Endpoints

IT Engineer Endpoints

Reposted 15 Hours Ago
3 Locations
Hybrid
132K-155K Annually
Mid level
Consumer Web • Healthtech • Professional Services • Social Impact • Software
Headway is building a new mental healthcare system rewired for access and affordability.
The Role
Own the full device lifecycle across macOS Windows (and ChromeOS) build BYOD and device-trust programs in a HIPAA-regulated environment integrate endpoint management with identity and automate onboarding/offboarding and remediation using scripting iPaaS and AI partner with Security and stakeholders own roadmap and participate in a light on-call rotation.
Summary Generated by Built In

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 75000 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: Iru 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.

Headway participates in E-Verify. To learn more click here.

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.

Skills Required

  • At least 3 years as a Client Platform / Endpoint / IT Systems Engineer
  • Deep hands-on experience managing macOS fleets at scale
  • Deep hands-on experience managing Windows fleets at scale
  • Hands-on experience managing ChromeOS fleets (ChromeOS is a plus)
  • Fluent in JAMF Pro
  • Fluent in Microsoft Intune
  • Familiarity with Google Chrome Enterprise Management
  • Solid knowledge of IAM; built and maintained workflows configured groups and policies
  • Scripting and automation experience (Bash Python or iPaaS like Tray.io Tines)
  • Experience building/operating BYOD programs and endpoint security/compliance controls in regulated environments (HIPAA SOC 2 HITRUST)
  • Experience with device trust attestation and posture management
  • Project management skills; owning a roadmap and reporting impact with data
  • Stakeholder management and cross-functional partnership to deliver large-scale endpoint changes
  • Participate in a light predictable on-call rotation

What the Team is Saying

Niki
Molly
April
Alicia

Headway Compensation & Benefits Highlights

  • Healthcare StrengthMultiple Cigna medical options with most premiums covered plus dental and vision FSAs life insurance and short/long‑term disability. Mental‑health access is reinforced by an HRA reimbursing eligible therapy costs up to $2100 per year and an EAP.
  • Parental & Family SupportUp to 16 weeks of fully paid parental leave for eligible full‑time employees. Inclusive family‑forming support is provided via Carrot Fertility.
  • Leave & Time Off BreadthFlexible/generous PTO is paired with 56 hours of paid sick time and 13 paid holidays including a year‑end break. This creates ample time‑off coverage for rest and recovery.

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The Company
HQ: New York NY
819 Employees
Year Founded: 2019

What We Do

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 1 in 4 people in the US have a treatable mental health condition but the majority of providers don’t accept insurance making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. Headway was founded in 2019. Since then we’ve grown into a diverse national network of over 60000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz) Accel GV (formerly Google Ventures) Spark Capital Thrive Capital Forerunner Ventures and Health Care Service Corporation.

Why Work With Us

The demand for mental health care has never been higher underscoring the need for solutions like Headway that increase accessibility to clinical care. 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.

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Headway Offices

Remote Workspace

Employees work remotely.

Headway employees work remotely across the US with the option to work from offices in New York City San Francisco and Seattle.

Typical time on-site: None
HQNew York NY
San Francisco CA
Seattle WA
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Date Posted

07/12/2026

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