Job Description
Level 2 Support 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, SharePoint, 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 week
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, SharePoint, 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 week
💡 Quick Summary
Seeking a career-building opportunity? The Technical Support Level 2 position is now open for candidates interested in the IT Engineer & Developer Jobs sector. This role in Chicago offers a professional environment and growth potential.
Requirement Snapshot: Candidates should possess basic communication skills, a proactive attitude, and the ability to work in a team. Experience in IT Engineer & Developer Jobs is a plus.
