Helpdesk Technician Level 1.; MSP

We built this MSP around proactive cloud, security, and long-term client partnerships. Our model is structured, efficient, and built to scale. We do not operate in chaos. We invest in tools, documentation, and training so our engineers can grow instead of burn out.

As we continue expanding across the Chicagoland market, we are hiring a Helpdesk Technician Level 1.5 to strengthen our frontline engineering team. This is an ideal role for someone with MSP experience who wants to sharpen their technical depth and move toward a Level 2 Systems Administrator seat.

You will work directly inside modern Microsoft environments, collaborating with senior engineers while owning real responsibility from day one.

• Resolve technical issues across Windows 10 and 11, Windows Server, and Microsoft 365 environments
• Administer Microsoft 365 including Exchange Online, Entra , Teams, SharePoint, and basic Intune management
• Handle user provisioning, device setup, access control, and MFA configuration
• Support onboarding and offboarding processes
• Assist with workstation deployments and light infrastructure tasks
• Contribute to clean documentation and structured processes

• At least 1 year of MSP experience
• Strong troubleshooting ability across Windows environments
• Working knowledge of Windows Server fundamentals
• Experience with Microsoft 5 administration
• Comfortable managing workload in a fast-moving environment
• Clear communicator who takes ownership

• Hybrid flexibility after onboarding
• Retirement plan with company match
• Certification bonuses and paid learning paths
• Weekly meal benefit
• Clear growth runway toward Systems Engineer