Tier 2 System Administrator

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 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

• 2-4+ years of IT support experience, ideally within an MSP or multi-client environment
• Strong experience with Microsoft 365 administration (mailboxes, Teams policies, SharePoint, security settings, Entra ID)
• Hands-on experience with virtualization technologies (VMware required; Hyper-V a plus)
• Familiarity with Azure AD, basic Azure services, and hybrid identity concepts
• Comfort working with firewalls and networking gear (WatchGuard, Barracuda, Aruba, etc.)
• Understanding of servers, storage, backups, and general sysadmin fundamentals
• Someone who doesn't fold under pressure, takes initiative, and isn't afraid to try to solve a problem before escalating
• A team-oriented, accountable engineer with strong communication skills
• A self-learner who enjoys continuous education, certifications, and building new skills

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

• Clear advancement path beyond help desk → systems, cloud, or project engineering
• High-growth MSP environment with real exposure to backend infrastructure
• Access to mentors who encourage learning rather than gatekeeping knowledge
• Opportunities to support everything from M365 → Azure → VMware → security → networking
• A culture that promotes from within and rewards initiative

Compensation & Benefits

• Target salary:
  $65,000–$80,000
  based on experience
• Medical, dental, and vision insurance
• Telemedicine and legal assistance benefits
• Short- and long-term disability
• 401(k) with company match
• 3 weeks PTO
• Certification bonuses & paid learning opportunities
• Weekly meal benefit through DoorDash
• Strong work-life balance within a supportive, award-winning team

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.