cover image
Insight Global

Windows Administrator

On site

Vancouver, Canada

Freelance

08-10-2025

Share this job:

Skills

Communication Adaptability ServiceNow Microsoft 365 Customer Service Operating Systems Windows Organization Windows 10

Job Specifications

JOB DESCRIPTION

Insight Global is looking for a Windows Administrator to join one of Canadas boutique financial institutions on a 2-month contract in Vancouver BC, to assist with their manual migration from Windows 10 -11.

The day to day of this role includes:

Conduct on-site operating system upgrades from Windows 10 to Windows 11 directly on workstations.
Perform manual updates on approximately 700-800 end-user devices, evenly split between Vancouver and Toronto (400 devices per city).
Follow documented processes to ensure machines are updated correctly and efficiently.
Work with both new hardware and refurbished devices, upgrading systems as necessary.
Coordinate and schedule upgrade times with end users to minimize disruptions.
Provide basic troubleshooting support to end users during and after the migration process.
Take ownership of device lists, scheduling, and upgrade logistics, with some assistance from the project team.
Ensure smooth rollout of the new operating systems, maintaining clear communication with users throughout the migration process.

REQUIRED SKILLS AND EXPERIENCE

Proficient in Windows 10 and Windows 11, including their features, updates, and troubleshooting techniques
Experience with Microsoft Intune for pushing updates and managing devices
Familiarity with the Microsoft 365 suite of applications, including cloud-based tools like OneDrive and SharePoint
Knowledge of ServiceNow for assisting users of submitting any tickets if experiencing issues
Skilled in basic troubleshooting tasks and service desk operations
Proven experience in manually migrating operating systems on workstations and following documented procedures
Strong customer service abilities
Adaptability to learn and support unique applications specific to the organization
Awareness of regulatory processes within the financial services or banking industry
Willingness to work onsite every day to assist users directly
Flexibility to work outside regular hours if needed, including accommodating late shifts

About the Company

Insight Global is an international professional services and staffing company specializing in delivering talent and technical solutions to Fortune 1000 companies across the IT, Non-IT, Healthcare, and Engineering industries. Fueled by staffing and talent experts, Evergreen, our professional services brand, brings technical advisors and culture consultants to help customers tackle their biggest challenges. With over 70 locations across North America, Europe, and Asia, and global staffing capabilities in 50+ countries, our tea... Know more