Level 2 Technician - Managed IT Services - MSP

NerdsToGo, Inc.; Chicago, Northern (IL, KY); Hybrid; USD 77,146,000 - 94,503,000; Full time

Benefits offered by this job

401(k)

Bonus based on performance

Dental insurance

Health insurance

Paid time off

Training & development

Vision insurance

Job summary

NerdsToGo, Inc. in Chicago Downtown is 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 hybrid role blends help desk support with field work for an experienced technician who communicates clearly with non-technical clients and can mentor junior techs. The ideal candidate has 3+ years in IT support, MSP environment exposure, strong Microsoft 365/Entra ID skills, and willingness to

Qualifications

• 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 networking experience — firewalls, switches, VLANs, VPNs, and Wi‑Fi; basic TCP/IP, DNS, DHCP.
• Current, valid driver’s license and ability to travel to client sites — required.
• Professional, patient communication with non-technical business clients.
• CompTIA A+/Network+/Security+ or Microsoft certifications a plus.

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.

Education

CompTIA A+/Network+/Security+ or Microsoft certifications

Tools

ConnectWise

Atera

NinjaOne

Job description

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).