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Added 7 mins ago
EA
Contracts Administrator
Effortless Admin Inc.
Edmonton, AB
- Full-time
…administration sector. We're seeking a detail-oriented Contracts Administrator who can grow with us. Initially, you'll focus on data entry and management for new client contract…
Added 8 mins ago
O
Sr. Engineer System administrator
OnX
Toronto, ON
- Full-time
We are seeking a highly skilled Senior Systems Administrator to join our Infrastructure Services team. This role is ideal for a hands-on technical professional who thrives in complex…
Added 39 mins ago
T
Senior Mongo DBA
TD
Toronto, ON · Mississauga, ON
- Full-time
The Senior Mongo Database Administrator is responsible for operational support, maintenance, and optimization of enterprise database platforms including Microsoft SQL Server and MongoDB.…
Added 1 hour ago
V
Senior Quality Management System (QMS) Quality Engineer
VitalBio
Oakville, ON
- Full-time
The Senior Quality Management System (QMS) Quality Engineer is a technical leader responsible for maintaining, improving, and ensuring the effectiveness of the Company's Quality Management…
Added 1 hour ago
PC
Senior Claims Assessor
People Corporation
Winnipeg, MB · Ottawa, ON · MB - Coughlin Kenaston - Wpg
- Full-time
We are seeking a Senior Claims Assessor to join our Coughlin & Associates team in Winnipeg, MB or Ottawa, ON.
Added 2 hours ago
T
Senior Mongo DBA
TD
Mississauga, ON
- Full-time
The Senior Mongo Database Administrator is responsible for operational support, maintenance, and optimization of enterprise database platforms including Microsoft SQL Server and MongoDB.…
Added 2 hours ago
FB
Sr. System Administrator
FGF Brands
Toronto, ON · Greater Toronto Area, Canada
- Full-time
Reporting to the Manager, IT Infrastructure, the Senior Systems Administrator will be responsible for the configuration, implementation, and maintenance of computer technologies maintained…
Added 2 hours ago
B
Sr. IT System & Network Administrator/Administrateur principal ou Administratrice principale, systèmes et réseaux TI
Bluberi
Drummondville, QC
- Full-time
Reporting to the Infrastructure Manager, the Sr. IT System & Network Administrator is a senior technical and delivery-focused role responsible for architecting, implementing, and evolving…
Added 2 hours ago
Bilingual Senior Specialist, Software Engineering (Environment Management)
CMHC - SCHL
Ottawa, ON · Montreal, QC
Join the Platform Engineering team, in the Senior Specialist, Software Engineering & Environment Management position, where we’re modernizing how CMHC builds and operates software…
Added 2 hours ago
AG
Senior Microsoft Administrator
Alamos Gold Inc.
Toronto, ON
- Full-time
Reporting to the IT Security and Solutions Manager, the Senior Microsoft Administrator plays a pivotal role in shaping the security, reliability, and future of the organization’s Microsoft…
Added 3 hours ago
YI
Software Developer - Internal Automation
YuJa Inc.
Toronto, ON · North York, Ontario
- $80,000 to $90,000 CAD / year
- Full-time
AZ-104 (Microsoft Azure Administrator Associate)
Added 3 hours ago
Branch Administrator - Temporary
Government of Alberta
AB
The Branch Administrator provides high-level operational and administrative coordination support to the Executive Director's Office and branch leadership. The position serves as a key…
Added 3 hours ago
RJ
Branch Administrator
Raymond James
AB
- Full-time
Work closely with the Senior Branch Administrator supporting staff initiatives & communications, onboarding and offboarding support staff, track and maintain staff vacations & absences and…
Added 4 hours ago
FB
System Administrator
fgf brands
Toronto, ON · Greater Toronto Area, ON
- Other
Reporting to the Manager, IT Infrastructure, the Senior Systems Administrator will be responsible for the configuration, implementation, and maintenance of computer technologies maintained…
Added 5 hours ago
BS
ServiceNow Developer
Brainhunter Systems Ltd
Toronto, ON
- Contract
5+ years experience as an administrator for ServiceNow platform
Added 19 hours ago
KG
Senior Technology Architect
K&K Global Talent Solutions INC.
Toronto, ON
- Full-time
Client is seeking for skilled Oracle Fusion Cloud OCI & Security Administrator to manage, support, and secure Oracle Cloud Infrastructure (OCI) and Oracle Fusion Cloud environments. The…
Added 19 hours ago
N
Gestionnaire des opérations d’affaires - Évaluation et services-conseils, Canada | Business Operations Manager, Canada Valuation & Advisory
Newmark
Montreal, QC
- Full-time
The Business Operations Manager, Canada Valuation and Advisory reports to the Senior Managing Director - Head of Operations Canada. This role interacts with most functions within the…
Added 20 hours ago
Q(
MONTREAL [HYBRID] - Storage Administrator
QUANTEAM (RAINBOW PARTNERS Group)
Montreal, QC · Greater Montreal Metropolitan Area
- Full-time
We are looking for a Senior Storage Administrator to work with one of our clients, an international financial institution based in Montreal.
Added 20 hours ago
Branch Administrator - Temporary
Government of Alberta
AB
The Branch Administrator provides high-level operational and administrative coordination support to the Executive Director's Office and branch leadership. The position serves as a key…
Added 20 hours ago
A4
Senior QMS / Quality Engineer ( Medical Devices)
Avenue 45
Mississauga, ON
- $110,000 to $145,000 CAD / year
- Full-time
Our direct client is looking for a Senior Quality Engineer / QMS with strong background in Medical Devices, working onsite in Oakville / Mississauga, ON, Canada.
Added 20 hours ago
D
Senior Administrator, Core Datastorage
Domtar
Montreal, QC
- Full-time
The location in Montreal , ( Quebec , Canada ), is seeking talent to fill the position of Senior Administrator, Core Datastorage . This job is full-time permanent .
Added 20 hours ago
Senior Specialist, Software Engineering (CI/CD & Automation Engineering)
CMHC - SCHL
Ottawa, ON · Montreal, QC
Join the Business Solutions Engineering team, in the Senior Specialist, Software Engineering (CI/CD & Automation Engineering) position, where you’ll work closely with the Platform…
Added 21 hours ago
MC
Level 2 3 Network Administrator & Projects Specialist (35949)
Myticas Consulting
Ottawa, ON
- Full-time
…onboardings, they are looking to add an experienced Level 2/3 Network Administrator & Projects Specialist to their Professional Services…
Added 21 hours ago
BL
Director of Operations and Human Resources
BC Legal Management Association
Vancouver, BC · Greater Vancouver Metropolitan Area
- Other
This is a senior leadership position offering significant responsibility across Firm operations, people and resource management, technology, facilities, marketing and strategic initiatives.
Added 21 hours ago
RJ
Branch Assistant
Raymond James
AB
- Full-time
Work closely with the Senior Branch Administrator supporting staff initiatives & communications, onboarding and offboarding support staff, track and maintain staff vacations & absences and…

Closed listing

VySystems

Windows Server Administrator

Toronto, ON, Canada

Contract

This opening has closed.

The original listing is kept below for reference.

Find open jobs More jobs with this employer

About employer

Job details

Job type: Contract
Closing date: 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

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Original job description

Archived listing. The details below describe a past opening.

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.

About employer

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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