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VySystems

Windows Server Engineer

Toronto, ON, Canada

Job type: Full-time
Apply by: Oct 21, 2026
Experience: 5+ years of hands-on experience administering and supporting Microsoft Windows Server environments (Windows Server 2012 and newer).
Posting language: English
Posted: Sep 21, 2026

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Original job description

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.

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More about this job

Responsibilities

The Windows Server Engineer will be responsible for administering, supporting, and upgrading Microsoft Windows Server environments within an enterprise setting. This role involves executing large-scale migrations, managing production deployments, and ensuring operational efficiency through automation and scripting.

Requirements

Candidates must have at least 5 years of experience in Windows Server administration and strong proficiency in PowerShell scripting. Expertise in infrastructure management tools, ITIL processes, and experience within regulated environments like financial services are highly preferred.

Skills

Windows Server
PowerShell
Automation
VMware vSphere
Microsoft Hyper-V
SCCM
MECM
SaltStack
Dynatrace
ServiceNow
ITSM
ITIL
Change Management
Troubleshooting
Infrastructure Management
Cloud Infrastructure

Visa sponsorship

Not detected in the job text

Keywords

Windows Server
PowerShell
Automation
VMware vSphere
Hyper-V
SCCM
MECM
SaltStack
Dynatrace
ServiceNow
ITSM
ITIL
Change Management
Patching
Migration
Cloud Infrastructure
MCSE
Azure
Financial Services
Infrastructure Management
Deployment
Governance
Release Management
Incident Management
Problem Management
Technical Documentation
Windows Server 2022
Windows Server 2025
Enterprise Environments
System Administration

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