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Added 18 mins ago
SL
Bilingual Senior Operations Specialist
Sun Life Québec
Montreal, QC
- Full-time
At Sun Life, we're driven by our Purpose: helping our Clients achieve lifetime financial security and live healthier lives. Our values shape how we work: caring, authentic, bold, inspiring,…
Added 20 mins ago
C
Senior Information Security Specialist
CIBC
Toronto, ON
- Full-time
As a member of CIBC’s CTPR team, you’ll play a crucial role in all matters of Information Security. As a Senior Information Security Specialist you will be responsible for consulting on…
Added 20 mins ago
C
IT Architecture Specialist
CAE
Ottawa, ON · Montreal, QC · Mirabel, QC · Halifax, NS
- Full-time
Ensure architecture designs comply with security, regulatory, and operational requirements.
Added 20 mins ago
Financial Services Specialist
Government of Alberta
AB
Reporting to the Senior Finance Lead, the Financial Services Specialist is responsible for the daily review and verification of a wide range of accounting entries, meeting daily deadlines,…
Added 35 mins ago
Sr. Technical Support Specialist
Open Text Corporation
Waterloo, ON
The Senior Technical Support Specialist is a key technical contributor within OpenText Global Technical Support. The role owns complex and highly visible client issues from investigation…
Added 49 mins ago
HR
Technical Specialist, Quality Assurance
Hitachi Rail
Toronto, ON
- Full-time
The Technical Specialist, Quality Assurance assumes the role of Quality Assurance Manager (QAM) within the Product/Project team organization and has the responsibility of assuring the…
Added 49 mins ago
HR
Technical Safety Specialist
Hitachi Rail
Toronto, ON
- Full-time
The Technical Safety Specialist provides technical safety leadership to the safety team, is responsible for enforcing the safety strategy, developing and continuously improving safety…
Added 1 hour ago
W
Senior Database Specialist
Walker
Niagara Falls, ON
- Full-time
We’re looking for a Senior Database Specialist to join our team and play a key role in supporting and evolving our SharePoint, SQL Server, Microsoft Access, reporting, and data integration…
Added 1 hour ago
SL
Bilingual Senior Operations Specialist
Sun Life
Toronto, ON · Waterloo, ON · Montreal, QC · Sun Life Toronto One York
- Full-time
At Sun Life, we're driven by our Purpose: helping our Clients achieve lifetime financial security and live healthier lives. Our values shape how we work: caring, authentic, bold, inspiring,…
Added 1 hour ago
SL
Senior People Operations Specialist
Sun Life
Toronto, ON · Waterloo, ON · Sun Life Toronto One York
- Full-time
At Sun Life, we're driven by our Purpose: helping our Clients achieve lifetime financial security and live healthier lives. Our values shape how we work: caring, authentic, bold, inspiring,…
Added 1 hour ago
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NPI & Trials IP Engineer
Nokia
Ottawa, ON
- Full-time
Acts as a role model for staff / work team / taskforces, often the most senior specialist in the team, who serves as best practice professional within own organizational unit and is…
Added 1 hour ago
S
Measurement Specialist
SECURE
Calgary, AB
- Other
At SECURE, we lead the way in waste management and energy infrastructure, providing unmatched security and peace of mind to our customers. Our strength lies in our size, extensive network,…
Added 1 hour ago
Y
Senior Windows Server Modernization Specialist
Yochana
Toronto, ON
- Full-time
Position Name – Senior Windows Server Modernization Specialist
Added 1 hour ago
CM
Specialist, Institutional & Pension Accounting
CIBC Mellon
Toronto, ON · Greater Toronto Area, Canada
- Full-time
The Specialist, Institutional & Pension Accounting administers the assigned corporate and institutional accounts and provides financial reporting according to predetermined time schedules…
Added 1 hour ago
CS
Specialist, Reliability
Corby Spirit and Wine Limited
Windsor, ON
- Full-time
This role reports directly to the Director of Engineering. The Reliability Specialist is responsible for championing new programs such as Reliability Centered Maintenance, Predictive…
Added 1 hour ago
OR
Quality Control Specialist
OSL Retail Services
Mississauga, ON
- $65,000 to $75,000 CAD / year
- Full-time
We are currently seeking a Quality Control Senior Specialist. This is a full-time, in-office role 5 days per week. This position requires strong technical product knowledge and business…
Added 1 hour ago
BH
Principal/ VP of Engineering
Blair Health
Toronto, ON
- Full-time
Blair is building the operating system for the next generation of healthcare, closing specialist gaps while enabling proactive, preventative care.
Added 1 hour ago
Specialist, Procurement – Enablement, Training and Communications
WestJet Group
Calgary, AB
Added 2 hours ago
Senior Security Specialist, AI Fabric
Bell
Regina, SK
We are seeking an experienced and results-oriented security leader to join Bell's Corporate Security team as Senior Specialist, AI Fabric Security.
Added 2 hours ago
CS
PUD Driver
COPE Sensitive Freight
Perth, ON
- Full-time
Added 2 hours ago
V
Windows Server Administrator
VySystems
Toronto, ON
- Contract
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…
Added 3 hours ago
C
SCADA Specialist
Certarus
AB · Calgary, AB
- Full-time
…across a mobile fleet and distributed customer sites. The SCADA Specialist, Ignition will help operate, support, configure, and enhance this platform so it remains reliable, secure, usable,…
Added 3 hours ago
L
Content Coordinator eBusiness / Coordonnateur(trice) de contenu eBusiness
Leviton
Pointe-Claire, QC
- Full-time
Reporting to the eBusiness Specialist, the Content Coordinator eBusiness supports the day-to-day operations of Leviton's digital B2C platforms. This role is responsible for coordinating…
Added 3 hours ago
Bilingual Senior Specialist, IT Portfolio and Performance Management
CMHC - SCHL
Toronto, ON · Ottawa, ON · Montreal, QC
Join CMHC’s IT Performance and Planning team, in the Bilingual Senior Specialist, IT Performance and Planning position, where you’ll play a key role in building and evolving the IT’s…
Added 3 hours ago
BP
Health And Safety Consultant
BlueSky Personnel Solutions
Toronto, ON
- $95,000 to $103,000 CAD / year
- Full-time
Our client located in Toronto is looking for a Bilingual Health, Safety and Attendance Specialist to add to their 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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