Demo

Level 2 Technician - Managed IT Services - MSP

NerdsToGo of Chicago Downtown, IL
Chicago, IL Full Time
POSTED ON 10/1/2026
AVAILABLE BEFORE 11/29/2026
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).

Salary : $27 - $33

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