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Added 2 days ago
MC
Level 2 3 Network Administrator & Projects Specialist (35949)
Myticas Consulting
Ottawa, ON
- Full-time
Current project work includes zero trust initiatives, data centre and server migrations, infrastructure modernization, Microsoft Intune deployments and broader cybersecurity initiatives.
Added 6 days ago
Senior Specialist, Software Engineering (.Net)
CMHC - SCHL
Ottawa, ON · Montreal, QC
Join the Technology and Business Transformation team, in the Senior Specialist, Software Engineering (.Net Developer) position, where the next generations of software applications are being…
Added 6 days ago
Bilingual Senior Specialist, Software Engineering (.Net)
CMHC - SCHL
Ottawa, ON · Montreal, QC
Join the Technology and Business Transformation team, in the Bilingual Senior Specialist, Software Engineering (.Net Developer) position, where the next generations of software applications…
Added 7 days ago
CO
Infrastructure and Cloud Specialist
City of Welland
Welland, ON
- $110,059 to $128,754 CAD / year
- Full-time
Reporting to the Chief Information Officer, the Infrastructure & Cloud Specialist is responsible for the administration, security, reliability and modernization of the City’s on-premises…
Added 10 days ago
HM
Senior Systems Administrator
HEB MANITOBA
Winnipeg, MB
- Full-time
The role is the escalation point for complex incidents, a mentor to the Technical Support Specialist team, and a hands-on contributor to HEB's technology modernization agenda. It operates…
Added 11 days ago
MD
Senior Systems / Cloud Engineer
Minnesota Direct Care and Treatment
Saint-Paul, NB · St.-Paul, NB
- Full-time
The Minnesota Attorney General’s Office (AGO) is seeking a highly skilled Senior Systems / Cloud Engineer to join our IT Division. In this senior level role, you will provide advanced…
Added 13 days ago
B
Senior Infrastructure Specialist – Digital Library Platforms
BMO
Toronto, ON
- Full-time
…digital future. We're looking for a highly skilled Infrastructure Specialist who thrives in complex enterprise environments and enjoys solving challenging technical problems across Linux,…
Added 20 days ago
Technical Customer Support Specialist – Level 3
Quadbridge
Vancouver, BC
The Technical Customer Support Specialist - Level 3, Modern Work, Data & AI is a senior escalation resource within Managed Services. The role owns complex incidents and service requests,…
Added 20 days ago
Senior OT Control Systems - Engineering Specialist
Mariner
Saint John, NB
Active Directory, Windows Server environments, VMware, and related OT infrastructure technologies.
Added 20 days ago
Senior OT Control Systems - Engineering Specialist
Mariner
Saint John, NB
Active Directory, Windows Server environments, VMware, and related OT infrastructure technologies.
Added 27 days ago
M
Senior Infrastructure Specialist
McKesson
Mississauga, ON
- Full-time
The Senior Infrastructure Specialist is responsible for planning, designing, and executing enterprise infrastructure modernization initiatives, including large‑scale migrations from legacy…
Added 1 month ago
JG
Senior Windows Server Modernization Specialist
J&M Group
Toronto, ON
- Contract
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…
Added 6 months ago
A
Systems Upgrade Specialist (Linux)
Anovia
Remote, Canada
- $60,000 to $70,000 CAD / year
- Full-time
- Remote
Anovia is seeking a Systems Upgrade Specialist to keep our Call Handling customer base on current, supported software releases. In this role, you will plan, schedule, and execute remote…
Added 2 months ago
S
Senior Quality Assurance Specialist
Synechron
Toronto, ON · Greater Toronto Area, Canada
- $120,000 to $125,000 CAD / year
- Full-time
…development initiatives in our FinLabs we develop solutions for modernization, from Artificial Intelligence and Blockchain to Data Science models, Digital Underwriting, mobile-first…
Added 2 months ago
C
Spécialiste principal Microsoft Dynamics Navision
CGI
Montreal, QC
- Full-time
Job Title: Senior Microsoft Dynamics NAV (Navision) Specialist – NAV 2009

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J&M Group

Senior Windows Server Modernization Specialist

Toronto, ON, Canada

Contract

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Job details

Job type: Contract
Apply by: Mar 3, 2027
Posting language: English
Posted: Sep 4, 2026

Original job description

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.

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More about this job

Responsibilities

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.

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.

Skills

Windows Server
PowerShell
VMware vSphere
Microsoft Hyper-V
SCCM/MECM
ServiceNow
ITIL
Change Management
Server Modernization
Cloud Infrastructure
SaltStack
Dynatrace
Infrastructure Administration
Troubleshooting
Patching
Migration Planning

Visa sponsorship

Not detected in the job text

Keywords

Windows Server 2012
Windows Server 2016
Windows Server 2022
Windows Server 2025
PowerShell
VMware vSphere
Hyper-V
SCCM
MECM
SaltStack
Dynatrace
ServiceNow
ITIL
Incident Management
Change Management
Problem Management
Release Management
MCSE
Azure
Cloud Engineering
Infrastructure Modernization
In-place Upgrade
Server Migration
Patching
Virtualization
Governance Frameworks
Technical Documentation
Production Support
Financial Services
IT Services

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