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 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 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