AI-Powered IT Support Specialist — Hybrid (Chicago)

Addison Group

Chicago (IL)

Hybrid

USD 75,000 - 95,000

Full time

2 days ago
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Benefits offered by this job

Medical, dental, vision
401(k)
Health savings account
Transit benefits
EAP
Travel assistance
Fitness center access
Disability & life insurance

Job summary

Addison Group in Chicago is seeking an experienced IT Support Specialist to join its internal technology team in a hybrid role, requiring 2 onsite days per week. The position centers on Windows 11, Microsoft 365, Active Directory, and business applications, with exposure to AI tools like Copilot for productivity and compliance.

You will troubleshoot hardware and software, support remote access, and assist with onboarding, documentation, and user training while delivering high-touch service to

Qualifications

  • 4–6+ years of IT support experience.
  • Proficiency with Microsoft 365 and Windows 11.
  • Experience with Active Directory and business applications.
  • Familiarity with AI tools like Copilot.

Responsibilities

  • Provide hands-on desktop, application, phone, and remote support.
  • Troubleshoot Windows 11, Microsoft 365, Outlook, and AD.
  • Support desktops, laptops, mobile devices, and conference tech.
  • Assist with VPN, Citrix, and Remote Desktop access.
  • Document steps and resolutions in the ticketing system.
  • Assist onboarding/offboarding and access provisioning.
  • Support AI tools adoption and Copilot.
  • Train employees on security practices and productivity tools.

Skills

Microsoft 365
Windows 11
Active Directory
Remote access (VPN)
Customer service
Ticketing systems
AI tools (Copilot)

Education

Bachelor’s or Associate degree in IT

Tools

ServiceNow
SysAid
Citrix
VPN
Remote Desktop

Job description

Addison Group in Chicago is seeking an experienced IT Support Specialist to join its internal technology team in a hybrid role, requiring 2 onsite days per week. The position centers on Windows 11, Microsoft 365, Active Directory, and business applications, with exposure to AI tools like Copilot for productivity and compliance.

You will troubleshoot hardware and software, support remote access, and assist with onboarding, documentation, and user training while delivering high-touch service to

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