Help Desk Technician Level 2; Partial WFH | MSP; Oak Brook

Position: Help Desk Technician Level 2 (Partial WFH | MSP) (Oak Brook) We are a well-established Managed Services Provider serving businesses across Chicagoland is looking for a Level 2 Help Desk Technician who thrives in a fast-paced, multi-client environment. This role is ideal for someone who enjoys troubleshooting deeper technical issues, working directly with clients, and supporting a wide range of systems across cloud and on-prem infrastructures. If youre ready to sharpen your skills, gain exposure to project work, and grow into more advanced responsibilities, this is the opportunity for you. What You Will Do Handle escalated tickets from Tier 1 involving desktops, servers, connectivity, and cloud applications Support Microsoft 365 administration, Azure Entra , Windows Server, and endpoint security tools Troubleshoot networking issues related to switches, firewalls, VPNs, and wireless Assist with onboarding, device deployments, and small project tasks under senior guidance Maintain accurate documentation in PSA/RMM tools and communicate clearly with clients Perform routine patching, updates, and maintenance to keep client environments stable Deliver professional client-facing support while managing priorities across multiple customers What You Bring A minimum of 1 year working for a Managed Service Provider Strong background in Microsoft 365, Windows OS, and general network troubleshooting Experience with MSP toolsets such as Autotask, Datto, Kaseya, or IT Glue Ability to diagnose issues across servers, desktops, email, VPN access, and security tools Comfortable speaking with end users and providing calm, professional support Motivated to grow into systems administration and eventually support project work Why This Role Stands Out Competitive salary between sixty-five thousand and seventy-five thousand dollars Hybrid work from home flexibility after ramp-up Profit sharing and company-matched retirement plan Medical, dental, and vision insurance Life, short-term, and long-term disability benefits Three weeks of PTO plus holidays Certification bonuses, advancement pathways, and structured training support Weekly meal benefit and a recognition program that rewards performance A collaborative MSP culture that supports your technical development and long-term growth Apply tot his job