System Administrator Tier 2.5 (MSP / Hybrid)

Join a growing Managed Services Provider that supports small and mid-sized businesses across the Chicagoland area. Our team combines the collaborative feel of a local MSP with the resources of a national organization. We value reliability, accountability, and continuous learning, and we are looking for a System Administrator who shares those same values.

This is an excellent opportunity for a mid-level MSP engineer who is ready to take on complex technical challenges while gaining project experience. You will manage escalations, configure and maintain servers, and assist with Microsoft 365 and Azure cloud migrations.

Responsibilities :

• Act as the escalation point for complex support issues across servers, networks, and cloud systems
• Configure and maintain Windows Server environments, Active Directory, and Group Policy
• Perform and support Microsoft 365 migrations including Exchange Online and OneDrive
• Work with Azure technologies including Entra ID, Intune, and Azure Virtual Desktop
• Troubleshoot network connectivity, DNS, DHCP, and VPN-related issues
• Collaborate on infrastructure upgrades and cloud transition projects with senior engineers
• Document all work in Autotask and Kaseya while maintaining high-quality service communication
• Perform onsite visits for client support, deployments, and maintenance

Qualifications :

Why You’ll Love It Here :