J&M GroupVerified Job Source

Senior Windows Server Modernization Specialist

Toronto, ON
On-site
Posted Sep 4, 2026
1 position

Opens an external site

Employment type: Contract
Experience level: Senior · 5+ years
Minimum education: Professional degree
Apply by: Mar 3, 2027
Posting language: English
Working hours: 40 hours per week
Seniority: Associate
Application method: Direct apply is available

Job summary

Lead and execute enterprise-wide Windows Server in-place upgrades from version 2016 to 2025. Perform readiness assessments, coordinate application testing, and provide production support for global infrastructure environments.

Job details

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.

What you’ll do

Requirements

Requires 5+ years of experience administering Windows Server environments with strong expertise in PowerShell automation and virtualization. Proficiency in ITIL processes and experience with enterprise change management is essential.