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Added 3 mins ago
RB
Financial Advisor
Royal Bank of Canada
Mystery Lake, MB · THOMPSON, Manitoba
- Full-time
This unique position calls on your client-focused advice expertise and natural problem-solving skills to maximize each client interaction by helping clients with their everyday banking,…
Added 3 mins ago
MT
Client Account Specialist
McCarthy Tétrault LLP
Calgary, AB
- Full-time
We are recruiting for a Client Account Specialist to join our team in the Calgary office. The successful candidate must have a minimum of 3 years of hands-on experience in managing…
Added 15 mins ago
MS
Energy Specialist (Engineering)
Metergy Solutions
Toronto, ON
- $60,000 to $75,000 CAD / year
- Full-time
As an Energy Specialist on the Commercial Services team, you will support the delivery of utility submetering and cost allocation reporting across our commercial portfolio.
Added 48 mins ago
T
Finance Operations Analyst III
TD
Dieppe, NB
- Full-time
Act as a key Finance Support resource / specialist or representative for own functional unit by providing technical subject matter expertise / analysis or operational process support
Added 48 mins ago
B
Senior Legal Counsel, Capital Markets Litigation
BMO
Toronto, ON · FCP
- Full-time
Advanced knowledge of subject matter legal requirements and the operations of a single client group.
Added 48 mins ago
B
Senior Counsel
BMO
Toronto, ON · FCP
- Full-time
Advanced knowledge of subject matter legal requirements and the operations of a single client group.
Added 1 hour ago
Senior Specialist, Software Engineering (Microsoft Dynamics 365 CRM)
CMHC - SCHL
Toronto, ON · Ottawa, ON · Montreal, QC
Join the Business Solutions Engineering team, in the Senior Specialist, Software Engineer (Microsoft Dynamics 365 CRM) position, where the next generations of software applications are…
Added 1 hour ago
Bilingual Senior Specialist, Software Engineering (Microsoft Dynamics 365 CRM)
CMHC - SCHL
Toronto, ON · Ottawa, ON · Montreal, QC
Join the Business Solutions Engineering team, in the Senior Specialist, Software Engineering (Microsoft Dynamics 365 CRM) position, where the next generations of software applications are…
Added 1 hour ago
AW
Directeur, Développement des affaires et Expérience client - Director, Business Development & Customer Experience
AJ Walter Aviation
Montreal, QC
- Full-time
Le Directeur, Développement des affaires et Expérience client, dirige la stratégie commerciale et clients d’AJW Technique pour ses services de réparation et de révision (MRO) de composants…
Added 1 hour ago
BT
Senior Tax Specialist / Reviewer
Baker Tilly Canada
Iqaluit, NU
- Full-time
Ensure firm procedures are followed consistently for authorization forms, CRA data import, paperless files, review assembly, and client follow-up.
Added 1 hour ago
BG
Tactical Marketing - Placement Year
BMW Group
Goodwood, ON
- Internship
…day one, while gaining practical insight into the corporate operations of a world-class automotive…
Added 2 hours ago
RB
Senior Manager, Application Development and Integration
Royal Bank of Canada
Toronto, ON
- Full-time
The Senior Manager will lead key Treasury Management integration projects driving client centric solutions ensuring seamless milestone tracking, transparent reporting, and successful…
Added 2 hours ago
WC
Social Media Videographer Specialist
Woola Capital
Coquitlam, BC
- Full-time
In this roll you’ll work closely with field technicians, leadership, and operations teams to translate real work into compelling digital storytelling that supports brand growth,…
Added 2 hours ago
Energy Specialist (Engineering)
Metergy Solutions
Toronto, ON
As an Energy Specialist on the Commercial Services team, you will support the delivery of utility submetering and cost allocation reporting across our commercial portfolio.
Added 2 hours ago
DF
Sales Specialist
DK Flooring Expert
Brampton, ON
- Full-time
Role Description The Sales Specialist is a full-time, on-site role based in Vaughan, ON. This position is responsible for greeting and consulting with homeowners, understanding their needs,…
Added 2 hours ago
C
Senior Specialist, Tax Reporting Operations & Regulatory Initiatives
CIBC
Toronto, ON
- Full-time
As a Senior Specialist, Tax Reporting Operations & Regulatory Initiatives, you will be responsible for ensuring that Tax Reporting delivers quality reporting to both the CRA and clients…
Added 3 hours ago
RB
Banking Advisor
Royal Bank of Canada
ON · ESSEX, Ontario
- Full-time
This unique position calls on your client-focused sales expertise and natural problem-solving skills to maximize each client interaction. Specifically, you help clients with their everyday…
Added 3 hours 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 3 hours ago
GB
Customer Service Specialist
Gee Beauty
Toronto, ON
- $50,000 to $60,000 CAD / year
- Full-time
Gee Beauty is a luxury beauty destination specializing in advanced skincare, brows, makeup, and elevated client experiences. We are passionate about helping clients look and feel their best…
Added 3 hours ago
V
Procurement Specialist
Vaco
Concord, ON
- $60,000 to $70,000 CAD / year
- Full-time
Proactively identify potential delays, shortages, or schedule changes before they impact operations.
Added 3 hours ago
GR
Health, Safety and Environmental Specialist
Goldbeck Recruiting
Pemberton, BC
- $60,000 to $100,000 CAD / year
- Full-time
Our client is with a leading Canadian licensed producer in the regulated cannabis industry. The organization is known for its innovation, commitment to quality, and global presence, with…
Added 4 hours ago
Y
Senior Windows Server Modernization Specialist
Yochana
Toronto, ON
- Full-time
Position Name – Senior Windows Server Modernization Specialist
Added 4 hours ago
Q(
Health & Safety Specialist
QEOSH (HSE) Staffing & Recruitment Inc.
Winnipeg, MB
- Full-time
We are supporting our mining client, which specializes in heli-portable diamond drilling, skid-mounted programs, and self-propelled track-mounted rigs, in hiring a Health & Safety…
Added 4 hours ago
DC
Junior Environmental Specialist- Remediation/Reclamation
DWB Consulting Services Ltd
BC
- $32 to $44 CAD / hour
- Full-time
…the resource sector. Kintera has a close-knit team, a diverse client base and a reputation for outstanding quality and service. Our offices are located across all regions of British…
Added 4 hours ago
FF
Customs Specialist
Frederick Fox
Canada
- Full-time
Due to continued growth, our client is seeking a proactive and detail-oriented Customs Specialist to join their dynamic team. In this role, you will be responsible for ensuring compliance…

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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