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J M Group Inc
Senior Windows Server Modernization SpecialistJ M Group Inc • Toronto, ON, Canada
Senior Windows Server Modernization Specialist

Senior Windows Server Modernization Specialist

J M Group Inc • Toronto, ON, Canada
5 hours ago
Job type
  • Full-time
  • Quick Apply
Job description

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.
  • Strong 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.
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Senior Windows Server Modernization Specialist • Toronto, ON, Canada

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