Windows 11 Upgrade Technician
Infrastructure & Support
DeerfieldIL Contract Sep 4, 2025

Job Title: Windows 11 Upgrade Technician

Job 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.

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