Windows Specialist

TechDoQuest; Toronto; On-site; CAD 90,000 - 120,000; Full time

Job summary

TechDoQuest is seeking an experienced Windows Server upgrade specialist to drive in-place upgrades from 2016 to 2025 across large enterprise environments in Toronto. You will assess readiness, plan, implement, validate, and provide post-upgrade support with coordination across applications and infrastructure teams.

The role emphasizes optimization, governance, and documentation, with opportunities to introduce automation and standardization throughout the modernization lifecycle.

Qualifications

• 5+ years in Windows Server environments (2012+).
• Strong PowerShell scripting and automation.
• Experience with large-scale upgrade and migration projects.
• Knowledge of virtualization and cloud-hosted Windows infrastructure.
• Familiarity with ITIL processes and ITSM platforms.

Responsibilities

• Lead Windows Server upgrades from 2016 to 2025 across enterprise environments.
• Perform readiness assessments, compatibility reviews, planning, implementation, and validation.
• Coordinate testing and remediation with application teams.
• Troubleshoot OS, app, and infra issues during upgrades.
• Develop and maintain technical docs, recovery plans, and standards.
• Ensure change governance and after-hours implementation readiness.
• Identify automation opportunities and drive lifecycle improvements.

Skills

PowerShell scripting

Windows Server administration

Upgrade planning

VMware vSphere

Hyper-V

ITIL/ITSM knowledge

SCCM/MECM

Change management

Communication

Documentation

Tools

VMware vSphere

SaltStack

Dynatrace

SCCM/MECM

ServiceNow

Job description

• 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.