CSS Tec logo

Windows 11 Upgrade Technician

CSS Tec
Department:Customer Service
Type:REMOTE
Region:Chicago, IL
Location:Deerfield, IL
Experience:Entry level
Estimated Salary:$40,000 - $60,000
Skills:
WINDOWS 11WINDOWS 10ACTIVE DIRECTORYGROUP POLICYIMAGING TOOLSTROUBLESHOOTINGCUSTOMER SERVICE
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Job Description

Posted on: September 5, 2025

Job Title: Windows 11 Upgrade TechnicianJob Overview: We are seeking a dedicated and detail-oriented Windows 11 Upgrade Technician to join our client and play a vital role in supporting seamless IT operations. This remote, 3-month contract position, with preference for candidates located near Deerfield, IL, focuses on upgrading end-user systems from Windows 10 to Windows 11 while ensuring minimal disruption and strong technical support throughout the process. Compensation:

  • Commensurate with experience

Work Schedule:

  • Monday – Friday, standard business hours

Key Responsibilities of the Windows 11 Upgrade Technician:

  • Perform Windows 11 upgrades across user devices with efficiency and accuracy
  • Troubleshoot and resolve software and hardware compatibility issues
  • Provide hands-on support to end-users during and after migration
  • Document processes, challenges, and resolutions for team reference
  • Verify that systems meet required security and compliance standards

Qualifications and Skills for the Windows 11 Upgrade Technician:

  • Proven experience performing Windows 10/11 upgrades and deployments
  • Strong technical troubleshooting and problem-solving skills
  • Familiarity with Active Directory, Group Policy, and imaging tools
  • Excellent communication and customer service abilities

Why Join Us? This opportunity allows you to leverage your technical expertise in a focused, short-term project with immediate impact. You’ll play a key role in ensuring smooth technology transitions for end-users, while gaining valuable experience in enterprise-level upgrades and IT support. About Us: Contemporary Staffing Solutions (CSS) is a trusted leader in providing contract, temporary, temp-to-hire, and direct hire staffing solutions. With decades of experience, we’ve grown from a staffing agency to a nationwide provider of workforce management solutions. Our niche recruitment expertise spans Accounting & Finance, Call Center & Office Support, Human Resources, Sales & Marketing, and Information Technology. Explore more about CSS and how we connect great talent with exceptional opportunities by visiting www.ContemporaryStaffing.com.

Originally posted on LinkedIn

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