We are hiring for a Senior Windows Server Modernization Specialist . The role focuses on enterprise-wide Windows Server modernization, including large-scale in-place upgrades, infrastructure administration, automation, troubleshooting, and production support.

A strong fit will have 5+ years of Windows Server experience with expertise in PowerShell, enterprise upgrades, virtualization, cloud-hosted infrastructure, and change management.

What You Bring

- 5+ years of hands-on experience administering and supporting Microsoft Windows Server 2012 and newer environments.
- Strong experience with PowerShell scripting and automation for deployments, validation, reporting, and operational efficiency.
- Proven expertise in Windows Server installation, configuration, upgrades, patching, troubleshooting, recovery, and validation.
- Experience planning and executing large-scale Windows Server upgrade and migration projects.
- Hands-on experience with VMware vSphere, Microsoft Hyper-V, and cloud-hosted Windows infrastructure.
- Strong understanding of enterprise Change Management and governance frameworks.
- Experience supporting maintenance windows, production deployments, releases, and implementation activities.
- Working knowledge of Microsoft SCCM/MECM, VMware SaltStack, Dynatrace, and related infrastructure management tools.
- Experience with ServiceNow and IT Service Management platforms.
- Solid understanding of ITIL Incident, Change, Problem, and Release Management processes.
- Strong analytical, troubleshooting, organizational, and time management skills.




- Excellent verbal and written communication skills with the ability to create technical documentation and work with technical and business stakeholders.

What You'll Do

- Lead and execute Windows Server 2016 to Windows Server 2025 in-place upgrade activities across enterprise environments.
- Perform server readiness assessments, compatibility reviews, upgrade planning, implementation, validation, and post-upgrade support.
- Coordinate application testing, validation, and issue remediation following server upgrades.
- Troubleshoot complex operating system, application, and infrastructure issues during upgrade and migration projects.
- Collaborate with application support, infrastructure operations, security, cloud engineering, and project stakeholders.
- Develop and maintain technical documentation, implementation procedures, recovery plans, and operational standards.
- Ensure compliance with enterprise change management, security, and operational governance processes.
- Participate in incident management, production support, maintenance windows, and after-hours implementations.
- Identify opportunities for automation, process improvement, and standardization throughout the server modernization lifecycle.
- Provide technical guidance on upgrade readiness, implementation planning, risk mitigation, and operational support.
- Support enterprise infrastructure environments consisting of thousands of Windows servers across global regions.

Nice to have

- Microsoft certifications such as MCSE, Azure, Windows Server, or equivalent.
- Experience supporting Windows Server 2022 and Windows Server 2025 environments.
- Experience working within highly regulated environments such as banking or financial services.

📌 Senior Windows Server Modernization Specialist (Toronto)
🏢 Ju0026M Group
📍 Toronto