Tier 2 System Administrator (MSP)

Tier 2 System Administrator (MSP) – Hybrid – Chicago, IL

A rapidly growing Managed Services Provider in the western Chicago suburbs is looking for a Tier 2 System Administrator to join their engineering team. This MSP has doubled its recurring revenue over the last 18 months and continues to grow aggressively and creating real advancement opportunities for someone who wants to move beyond traditional help desk work and into deeper systems, cloud, and virtualization responsibilities.

This is an environment built for people who take ownership, enjoy solving technical challenges end-to-end, and want to grow into a well-rounded systems engineer. You’ll work directly with senior engineers and tech leads, gain exposure to backend infrastructure, and support clients across diverse industries.

This role is hybrid : onsite in Lisle (60532) for the first 4–5 weeks of training, then 2 days onsite / 3 days remote.

Must have MSP experience.

What You’ll Do

• Work Tier 2 tickets end-to-end with deeper troubleshooting across servers, cloud services, and critical infrastructure
• Support Microsoft 365, including Exchange Online, Teams, SharePoint, and Entra ID configuration and administration
• Manage Active Directory user administration, permissions, GPOs, and identity-related issues
• Maintain and support virtualization environments (VMware, Hyper-V)
• Troubleshoot networking issues involving DHCP, DNS, VPNs, VLANs, and firewall appliances
• Participate in project deployments : server builds, workstation refreshes, cloud migrations, and security implementations
• Use PSA, RMM, and documentation platforms (Autotask, Datto RMM, ITGlue) to track and resolve issues
• Act as a trusted escalation point for Tier 1 engineers
• Collaborate with senior engineers while continuing to take on more complex work as your skill set grows

What We’re Looking For

Why This Is a Strong Fit for a Tier 2 Who Wants More

Compensation & Benefits

Ready to Step Into a True Tier 2 / Sysadmin Path?

If you’re a Level 2 engineer who wants to grow into a full systems role, get deeper into virtualization and Microsoft 365 / Azure, and be part of a high-growth MSP that actually invests in you, this is your next move.