Senior System Administrator (MSP / Hybrid WFH) (Chicago)

Senior System Administrator (MSP / Hybrid WFH)

Location: Chicago, IL

Work Model: Local Hybrid WFH with client site visits as needed

Salary: $110,000 to $120,000

MSP Experience: Required

Azure Virtual Desktop Experience: Required

Senior MSP Infrastructure Role

We are a growing Chicago area Managed Services Provider hiring a Senior System Administrator to serve as a senior technical resource for complex escalations, infrastructure projects, and client facing engineering work.

This is a hands on technical role, not service desk management or project management. You will own the technical execution of advanced L2/L3 issues and infrastructure projects while working closely with the Project Manager and technical leadership.

Azure Virtual Desktop experience is required. You should be comfortable supporting and migrating client environments into AVD, including moving traditional Terminal Server or Remote Desktop environments to Microsoft cloud based desktops.

What You Will Work On

• Resolve advanced L2/L3 escalations across Windows Server, Active Directory, Microsoft 365, Entra ID, Intune, networking, and client infrastructure

• Troubleshoot server, virtualization, storage, backup, firewall, VPN, wireless, and application issues

• Design and execute infrastructure upgrades involving servers, virtualization, networks, firewalls, and wireless environments

• Lead Microsoft 365, Azure, and Azure Virtual Desktop migrations

• Execute technical projects including staging, migrations, cutovers, and infrastructure modernization

• Conduct client infrastructure assessments and identify technical risks, lifecycle needs, and improvement opportunities

• Scope technical projects and present recommendations to business owners and client leadership

• Support cybersecurity initiatives including CIS Controls, NIST CSF reviews, security questionnaires, and remediation

What We Are Looking For

• 5+ years of MSP experience, including advanced escalation and project work

• Hands on Azure Virtual Desktop experience with deployments, migrations, administration, and troubleshooting

• Strong Microsoft infrastructure experience across Microsoft 365, Azure, Entra ID, Intune, Windows Server, Active Directory, and Hyper V or VMware

• Strong networking knowledge across firewalls, VLANs, routing, VPNs, switching, and wireless

• Experience delivering infrastructure projects from design and staging through migration and cutover

• Strong client communication, documentation, troubleshooting, and technical ownership

Why Join

• $110,000 to $120,000 base salary depending on experience

• Hybrid WFH flexibility with Chicago area client visits (80% at home, 20% onsite)

• 100% company paid Blue Cross Blue Shield healthcare after 30 days

• 401(k) with 4% company match after one year

• Year end profit sharing

• Unlimited PTO based on performance and team coverage

• Professional development assistance

• Mileage reimbursement for client travel

• Opportunity to own advanced technical work across infrastructure, Azure, AVD, cybersecurity, and complex MSP projects