Service Desk Engineer; L2​/L3

Service Desk

As a Service Desk Engineer (L2/L3) at Reboot, Inc., you’ll provide advanced remote technical support, investigate and resolve escalated incidents, and keep our customers’ workplaces running smoothly. You’ll work extensively with Microsoft 365, Intune/Endpoint Manager, and Power Shell to troubleshoot, automate, and improve support outcomes. You’ll also help grow the team by mentoring and supporting junior engineers.

• Troubleshoot and resolve complex, escalated support issues remotely.
• Support and administer Microsoft
  365 services (e.g. Entra , Exchange, SharePoint, Teams).
• Manage and troubleshoot devices and policies with Intune/Endpoint Manager.
• Use Power Shell to diagnose issues, automate tasks, and improve support efficiency.
• Mentor and guide junior service desk engineers, sharing knowledge and best practices.
• Document solutions and contribute to a high-quality knowledge base.

You have 3-5 years of experience in a service desk, IT support, or MSP environment, with hands‑on expertise in Microsoft 365, Intune/Endpoint Manager, and Power Shell. You’re a confident troubleshooter who can handle complex issues, prioritize effectively, and communicate clearly with users and teammates.

Experience supporting a modern, cloud‑first workplace, improving support processes, or contributing to automation (e.g., scripts, tooling, or knowledge resources). Prior experience mentoring or coaching junior engineers is also a plus.

This is a remote role, where you’ll provide high‑quality support and collaborate with the team from home using our standard tools and practices.

Department

Service Desk

Reports to

Service Desk Coordinator

Work arrangement

Remote Work

May include an on‑call arrangement

230 E Ohio Street
Suite 410 1494
Chicago, IL 60611

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Support:
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