Intermediate Windows Systems Administrator to support a large-scale Windows 11 migration project for a crown corporation client!

Our valued crown corporation client is seeking an Intermediate Systems Administrator to support a large-scale Windows 11 migration project involving legacy applications and complex upgrade paths!

Initial 3-month contract with possibility of extension. On-site in Ottawa, ON - 7.5 hours per day, Monday to Friday.

Responsibilities:

• Assist in planning and executing an enterprise-wide migration from Windows 10 to Windows 11, with a focus on in-place upgrades where feasible
• Analyze existing systems, legacy applications, and compatibility constraints, especially older DLL-based dependencies
• Use SCCM (System Center Configuration Manager) to manage, deploy, and report on upgrade readiness and rollout status
• Maintain and manage Active Directory, ensuring account integrity and proper group policy alignment throughout the migration
• Collaborate with application owners and business units to validate post-migration functionality and address compatibility issues
• Troubleshoot and resolve Windows OS-related issues that may arise during or post-migration
• Support the development of documentation and SOPs for migration procedures, rollback plans, and known issues
• Ensure cybersecurity compliance and contribute to risk mitigation planning during upgrade activities

Must Have Skills:

• 5+ years of experience as a Windows Systems Administrator in enterprise environments
• Strong hands-on experience with Windows 10/11, including upgrade strategies and in-place migrations
• Solid knowledge of SCCM for deployment, patching, and upgrade orchestration
• Proficiency with Active Directory (GPO, OU structure, permissions)
• Demonstrated ability to assess and handle legacy application compatibility challenges

Nice-to-have Skills:

• Experience dealing with legacy Windows applications and environments containing outdated DLLs
• Exposure to automation or scripting tools (e.g., PowerShell) to streamline migration tasks
• Previous experience working on large-scale upgrade or transformation projects in public sector or regulated environments
• Familiarity with Intune, Azure AD, or hybrid identity management solutions
• ITIL Foundation certification