Windows / Active Directory Rollout Technician - Westchester, NY

Overview

On Site
$25 - $35
Contract - W2
Contract - 12 Week(s)

Skills

active directory
windows
os
rollout
pc
MDT
SCCM
Clonezilla
migration
upgrade
windowns 10
window
Group Policy
windows 11
CompTIA A+
Network+

Job Details

Job Title: Windows Rollout Technician

Location: Westchester County
Schedule: Monday to Friday, 8:30 AM 5:00 PM
Position Type: Contract

Pay Rate: [$30/hour W2]
Assignment Duration: 12 Weeks
Department: Information Systems / IT

Position Summary:

We are seeking Windows Rollout Technicians to assist with the deployment and support of a Windows operating system upgrade across our organization. The ideal candidate will have hands-on experience with desktop/laptop imaging, software installation, end-user support, and hardware troubleshooting in enterprise environments.

This is a project-based role supporting a system-wide technology upgrade initiative. Strong customer service, attention to detail, and technical skills are essential.

Key Responsibilities:

  • Perform Windows OS upgrades and migrations on desktops, laptops, and other endpoints.
  • Image, configure, and deploy workstations using standardized tools and procedures.
  • Install, test, and verify software applications and peripheral functionality.
  • Backup and restore user data and settings as needed during migration.
  • Troubleshoot post-deployment issues and provide desk-side/end-user support.
  • Track assets and update documentation related to hardware, software, and deployment status.
  • Collaborate with the IT team to escalate issues and ensure smooth transitions.
  • Maintain excellent communication with end-users throughout the upgrade process.

Qualifications:

  • Proven experience with Windows 10/11 rollout, upgrade, or migration projects.
  • Knowledge of imaging tools (e.g., MDT, SCCM, Clonezilla, etc.).
  • Familiarity with Active Directory, Group Policy, and enterprise IT environments.
  • Strong hardware/software troubleshooting and technical problem-solving skills.
  • Excellent interpersonal and communication abilities with end-users.
  • Ability to work independently, follow processes, and document tasks accurately.
  • Must be able to lift and move computer equipment as needed.
  • Previous healthcare IT or enterprise environment experience is a plus.

Preferred Skills & Certifications:

  • CompTIA A+, Network+, or other relevant IT certifications.
  • Experience with ticketing systems (e.g., ServiceNow, Remedy).
  • Experience working in healthcare or regulated environments.

Additional Notes:

  • This position is part of a larger Windows Upgrade Rollout Project across the organization.
  • Some positions may be allocated to specific locations or departments (e.g., Health Alliance).
  • All onboarding documents, including attestation forms, must be completed before the start date.

Interested candidates should be prepared for a fast-paced, hands-on technical role with a focus on quality and customer satisfaction.

Employers have access to artificial intelligence language tools (“AI”) that help generate and enhance job descriptions and AI may have been used to create this description. The position description has been reviewed for accuracy and Dice believes it to correctly reflect the job opportunity.