Windows Server Modernization Specialist

Position: Senior Windows Server Modernization Specialist Location: Toronto ON Mode of Work: Hybrid (2-3 days a week) Summary : We are looking for an experienced Windows Infrastructure professional to support the Client's enterprise-wide Windows Server Modernization Program. The successful candidate will be responsible for planning, coordinating, and executing large-scale in-place upgrades from Windows Server 2016 to Windows Server 2025 across mission-critical enterprise environments. The role requires strong expertise in Windows Server administration, virtualization, automation, troubleshooting, production support, and enterprise change management. Roles & Responsibilities: Lead and execute Windows Server 2016 to Windows Server 2025 in-place upgrade activities across large enterprise environments. Perform server readiness assessments, compatibility reviews, upgrade planning, implementation, validation, and post-upgrade support. Coordinate application testing, validation, and issue remediation activities following server upgrades. Troubleshoot complex operating system, application, and infrastructure-related issues during upgrade and migration projects. Collaborate with application support teams, infrastructure operations, security, cloud engineering, and project stakeholders to ensure successful project delivery. 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 as required. Identify opportunities for automation, process improvement, and standardization throughout the server modernization lifecycle. Provide technical guidance regarding upgrade readiness, implementation planning, risk mitigation, and operational support. Support enterprise infrastructure environments consisting of thousands of Windows servers across global regions. Qualifications & Skills: 5+ years of hands-on experience administering and supporting Microsoft Windows Server environments (Windows Server 2012 and newer). 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 in enterprise environments. 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 (Salt), Dynatrace, and related infrastructure management tools. Experience with ServiceNow and IT Service Management (ITSM) 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 engage effectively with technical and business stakeholders. Microsoft certifications (MCSE, Azure, Windows Server, or equivalent) are considered a strong asset. Experience supporting Windows Server 2022 and Windows Server 2025 environments is preferred. Experience working within highly regulated environments such as banking or financial services is preferred.

Lead and execute large-scale in-place upgrades from Windows Server 2016 to Windows Server 2025 across enterprise environments. Coordinate with stakeholders to perform readiness assessments, application testing, and post-upgrade validation.

Requires 5+ years of experience in Windows Server administration with strong proficiency in PowerShell and virtualization technologies. Experience in highly regulated environments like banking and knowledge of ITSM platforms is preferred.

• Technical DocumentationPreferred
• Change ManagementPreferred
• TroubleshootingPreferred

Identified from the job description. Confirm important requirements above.

• Windows Server Administration
• PowerShell Scripting
• VMware vSphere
• Microsoft Hyper-V
• Microsoft SCCM/MECM
• ServiceNow
• ITIL
• Change Management
• Server Modernization
• Infrastructure Automation
• Troubleshooting
• Technical Documentation

• Technology
• Software
• Finance & Accounting
• Consulting
• Engineering

Minimum education

Professional degree

Minimum experience

5+ years

Apply by

Oct 4, 2026

Posting language

English

Working hours

40 hours per week

Office presence

3 days per week

Seniority

Mid-Senior level

Application method

Direct apply is available