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 qualified 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.

📌 Windows Server Modernization Specialist (Toronto)
🏢 VySystems
📍 Toronto