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Added 29 mins ago
Q
Lead Implementation Manager
Quandri
Vancouver, BC
- Full-time
…understanding of insurance processes, systems, and data with serious technical capability and proprietary models, so the transformation is tangible and operational rather than…
Added 29 mins ago
M
Specialist, Environmental Affairs
Morguard
Mississauga, ON
- Full-time
The Specialist, Environmental Affairs is accountable to the Manager, Environmental Affairs in the support, enhancement and promotion of Morguard’s environmental management system and…
Added 29 mins ago
C
Software Implementation Specialist
CATALIS
AB · Edmonton, AB
- Full-time
We are seeking a proactive and customer-oriented Software Implementation Specialist to join our dynamic Payments team. In this role, your primary focus will be understanding business rules…
Added 29 mins ago
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Senior Advisor, Strategy, Planning & Partnerships
Metrolinx
Toronto, ON · Greater Toronto Area, Canada
- $93,798 to $127,484 USD / year
- Full-time
…Business Analytics, Business Administration (MBA) or an advanced/specialist technical certification, requiring an equivalent number of years of post-secondary…
Added 29 mins ago
AH
Accounts Receivable Specialist
Axxel HR
Toronto, ON
- Full-time
The Accounts Receivable Specialist is responsible for the timely collection and accurate application of customer payments for North America. The role manages customer accounts throughout…
Added 29 mins ago
MB
SPÉCIALISTE PRINCIPAL(E), EDI ET INTÉGRATIONS (Senior EDI & Integrations Specialist)
MADE BY GATHER
Montreal, QC
- Full-time
Added 30 mins ago
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AI Implementation Specialist, Calls
Buyerlink
Victoria, BC
- Full-time
We're looking for a curious, detail-oriented AI Implementation Specialist to join our team at an exciting inflection point. As AI becomes core to how we operate, you'll be the person…
Added 1 hour ago
BH
Account Manager - Downstream Chemicals
Baker Hughes
Leduc, AB
- Full-time
…satisfaction. You will work closely with customers, sales support, technical teams, and internal stakeholders to deliver tailored solutions, strengthen business relationships, and achieve…
Added 1 hour ago
T
PLM Functional Analyst - 3DEXPERIENCE
Techso
Montreal, QC
- Full-time
In this role, you'll be much more than a CAD specialist. You'll become a trusted advisor, helping clients understand their business needs, recommend innovative solutions, and support the…
Added 1 hour ago
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IT Architecture Specialist-EN
CAE
Halifax, NS
- Full-time
Lead technical design sessions and provide architectural guidance throughout the project lifecycle.
Added 1 hour ago
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Cyber Implementation Specialist-EN
CAE
Ottawa, ON
- Full-time
CAE Defence & Security Canada is seeking a Cyber Implementation Specialist to support the design, integration, implementation, and sustainment of cybersecurity solutions across Defence &…
Added 1 hour ago
MC
Yardi Support Specialist (2 Year Contract)
Medallion Corporation
Toronto, ON
- Contract
We are seeking a detail-oriented, analytical Yardi Support Specialist (Contract) to manage day-to-day application support and technical troubleshooting across our residential, commercial,…
Added 1 hour ago
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IT Architecture Specialist-EN
CAE
Ottawa, ON
- Full-time
Lead technical design sessions and provide architectural guidance throughout the project lifecycle.
Added 1 hour ago
C
IT Architecture Specialist-EN
CAE
Montreal, QC
- Full-time
Lead technical design sessions and provide architectural guidance throughout the project lifecycle.
Added 2 hours ago
Franchise Specialist, Business Banking - Richmond, BC/Winnipeg, MB
Scotiabank
SK · Winnipeg, SK
The Franchise Specialist is part of a national team responsible for leveraging market area expertise for the profitable growth of the Bank’s franchising portfolio in their region and for…
Added 2 hours ago
UO
Research Platform Cloud Designer -Information Technologies
University of Calgary
Calgary, AB
- Full-time
This position reports to the Senior Specialist, Research Platform Design within Research Computing Services (RCS). This is a Full-time Fixed Term position and is part of the AUPE Collective…
Added 2 hours ago
LS
Supervisor, Trust Safety (Audit and Compliance)
Law Society of Alberta
Calgary, AB
- Full-time
Participate in the development and implementation of risk-based approaches to Trust Safety oversight.
Added 2 hours ago
MC
IT Operations & Systems Support Specialist (34762)
Myticas Consulting
Ottawa, ON
- Contract
We are seeking a hands-on IT Systems Support Specialist to provide technical support across a complex, highly operational technology environment.
Added 2 hours ago
MC
Level 2 3 Network Administrator & Projects Specialist (35949)
Myticas Consulting
Ottawa, ON
- Full-time
Own projects from initial scoping and technical design through implementation, testing, documentation and operational handoff.
Added 2 hours ago
MS
Energy Specialist (Engineering)
Metergy Solutions
Toronto, ON
- $60,000 to $75,000 CAD / year
- Full-time
…Analyst will gain exposure across reporting delivery, developing technical submetering solutions, meter implementation, real-time metering data analytics, with a primary focus on executing…
Added 2 hours ago
LS
Supervisor, Trust Safety (Audit and Compliance)
Law Society of Alberta
Calgary, AB
- Full-time
Participate in the development and implementation of risk-based approaches to Trust Safety oversight.
Added 2 hours ago
Applied IoT & Data Specialist
Mohawk College
Hamilton, ON
Reporting to the General Manager, Energy & Power Innovation Centre (EPIC), the Applied IoT and Data Specialist will serve as a senior resource to projects in the areas of software…
Added 2 hours ago
B
AI Implementation Specialist, Calls
Buyerlink
Victoria, BC
- Full-time
We're looking for a curious, detail-oriented AI Implementation Specialist to join our team at an exciting inflection point. As AI becomes core to how we operate, you'll be the person…
Added 2 hours ago
S-
AI Specialist
SPE - Serruya Private Equity
Markham, ON
- Full-time
Serruya Private Equity is seeking an AI Specialist to support the practical adoption and implementation of artificial intelligence across our organization.
Added 2 hours ago
E9
Network Specialist
E-Comm 9-1-1 | Emergency Communications for British Columbia Incorporated
Vancouver, BC
- $112,361 to $117,249 CAD / year
- Full-time
We are seeking an experienced Network Specialist to join our highly technical Network Services team.

VySystems

Windows Server Administrator

Toronto, ON, Canada

Contract

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Job details

Job type: Contract
Apply by: Nov 4, 2026
Experience: Qualifications & Skills: 5+ years of hands-on experience administering and supporting Microsoft Windows Server environments (Windows Server 2012 and newer).
Posting language: English
Posted: Oct 5, 2026

Original job description

This job posting is for an existing, active vacancy and we are looking to hire a Senior Windows Server Modernization Specialist. 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.

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More about this job

Responsibilities

Plan and execute enterprise-scale in-place upgrades from Windows Server 2016 to Windows Server 2025, including readiness assessments, implementation, validation, and post-upgrade support. Coordinate application and infrastructure teams, troubleshoot issues, maintain technical and recovery documentation, and ensure compliance with change, security, and operational governance processes.

Requirements

Requires at least five years of hands-on Windows Server administration experience, strong PowerShell automation skills, and experience delivering large-scale enterprise upgrades or migrations. Candidates should also have virtualization and cloud infrastructure experience, familiarity with enterprise management and ITSM tools, and knowledge of ITIL and change management; relevant Microsoft certifications and regulated-industry experience are preferred.

Skills

Windows Server Administration
Windows Server Upgrades
PowerShell Scripting
Automation
VMware vSphere
Microsoft Hyper-V
Cloud Infrastructure
Troubleshooting
Server Migration
Change Management
SCCM/MECM
SaltStack
Dynatrace
ServiceNow
ITIL
Technical Documentation

Visa sponsorship

Not detected in the job text

Keywords

Windows Server 2012
Windows Server 2016
Windows Server 2022
Windows Server 2025
PowerShell
VMware vSphere
Microsoft Hyper-V
Cloud-Hosted Windows Infrastructure
SCCM/MECM
VMware SaltStack
Dynatrace
ServiceNow
IT Service Management
ITIL
Incident Management
Change Management
Problem Management
Release Management
Enterprise Infrastructure
Server Modernization
Server Upgrades
Server Migration
Patching
Production Support
Application Testing
Recovery Planning
Security Governance
Microsoft Certifications
Financial Services

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