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 you’re 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 ID, 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 ProviderStrong background in Microsoft 365, Windows OS, and general network troubleshootingExperience with MSP toolsets such as Autotask, Datto, Kaseya, or IT GlueAbility to diagnose issues across servers, desktops, email, VPN access, and security toolsComfortable speaking with end users and providing calm, professional supportMotivated to grow into systems administration and eventually support project workWhy This Role Stands Out
Competitive salary between sixty-five thousand and seventy-five thousand dollarsHybrid work from home flexibility after ramp-upProfit sharing and company-matched retirement planMedical, dental, and vision insuranceLife, short-term, and long-term disability benefitsThree weeks of PTO plus holidaysCertification bonuses, advancement pathways, and structured training supportWeekly meal benefit and a recognition program that rewards performanceA collaborative MSP culture that supports your technical development and long-term growth