Benefits:

401(k)
Bonus based on performance
Dental insurance
Health insurance
Paid time off
Training & development
Vision insurance

Job Summary

NerdsToGo of Chicago Downtown is a growing managed IT services (MSP) provider supporting small and mid-sized businesses across Chicago. We are hiring a full-time Level 2 Technician to own escalated tickets, client on-site visits, and hands-on infrastructure work across multiple client environments. This is a hybrid help desk + field role for an experienced technician who works independently, communicates clearly with non-technical clients, and can mentor junior techs.

Responsibilities

Serve as the escalation point for Level 1 tickets and own complex issues through resolution
Provide on-site support at client locations throughout the Chicago area (regular on-site visits; company vehicle provided)
Administer Microsoft 365, Entra ID/Azure AD, and Windows Server across multiple client networks
Configure and troubleshoot firewalls, switches, access points, VPNs, and Wi-Fi
Manage endpoints via RMM/MDM tools; handle imaging, deployments, and patching
Perform server maintenance, backup/disaster-recovery verification, and security hardening
Document client environments and resolutions in the PSA/ticketing system
Support client onboarding projects, hardware rollouts, and network buildouts
Mentor Level 1 technicians and contribute to runbooks and SOPs

Requirements

3+ years of hands-on IT support experience, including Tier 2 troubleshooting
MSP or multi-client environment experience strongly preferred (ConnectWise, Atera, NinjaOne, or similar RMM/PSA tools a plus)
Strong Microsoft 365 / Entra ID administration skills
Hands-on experience with business networking — firewalls, managed switches, VLANs, VPNs, and business-grade Wi-Fi — plus solid fundamentals (TCP/IP, DNS, DHCP)
Current, valid driver's license and the ability to travel to client sites as needed — required
Professional, patient communication with non-technical business clients
CompTIA A+/Network+/Security+ or Microsoft certifications a plus

Pay & Schedule

$27–$33 per hour based on experience. Full time, based in downtown Chicago with regular travel to client sites in the metro area (company vehicle provided).

Level 2 Technician - Managed IT Services - MSP

Quick Summary

Location & Eligibility

Listing Details

Posting Health

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