Technical Support Level 2
Innovative Systems Group
Remote
Full-Time
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Job Description
Type:
full-timeJob Description:
Level 2Support Technician Location:
South Loop, Chicago, IL Schedule:
Hybrid - onsite 3 days per week Responsibilities Handle Tier 2 escalations from the service desk Troubleshoot and resolve issues related to Windows workstations, servers, networking, Microsoft 365, and cloud services Support client environments using Autotask , Datto RMM , and IT Glue Perform remote and onsite troubleshooting for hardware, software, network, and user access issues Monitor alerts, remediate issues, and follow documented procedures Maintain accurate ticket notes, time entries, documentation, and client records Create and update technical documentation in IT Glue Assist with onboarding/offboarding users, device setup, application support, and permissions Escalate complex issues when needed while maintaining ownership and communication Participate in project work such as workstation deployments, migrations, and client environment improvements Deliver a high level of customer service to end users and client stakeholders Required Qualifications 2+ years of experience in an MSP or multi-client support environment Strong troubleshooting skills across Windows desktop, Windows Server, Microsoft 365, networking, and endpoint management Hands-on experience with Autotask , Datto RMM , and IT Glue Familiarity with Entra ID / Azure AD, Exchange Online, Point, OneDrive, and Teams Experience supporting printers and common business applications Ability to document clearly, follow processes, and manage multiple tickets at once Strong communication skills and a service-first mindset Ability to work onsite in the South Loop three days per weekSimilar remote jobs
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