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Added 1 hour 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 1 hour ago
KG
IAM Automation Engineer (Python & PingDS Focus)
K&K Global Talent Solutions INC.
Quebec, QC
- Full-time
We are seeking a highly analytical IAM Automation Engineer who uniquely bridges the gap between Identity & Access Management (IAM) infrastructure and core Python software engineering. In…
Added 1 hour ago
D
Programmer analyst, System and infrastructure operations, maintenance and development
Desjardins
Montreal, QC · Levis, QC
- Full-time
As a systems and infrastructure development, operations and maintenance programmer analyst, you participate in IT efficiency and quality by analyzing, designing, configuring, developing,…
Added 2 hours ago
SR
OT Controls Systems Specialist
Strathcona Resources Ltd.
Lloydminster, AB · Cold Lake, AB · Calgary, AB
- Full-time
We are seeking an experienced OT Control Systems Specialist to join the team responsible for the control systems, networks, infrastructure, and cyber security that Strathcona's field…
Added 2 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 3 hours ago
MC
DevOps Specialist - Kubernetes (35700)
Myticas Consulting
Ottawa, ON
- Full-time
We are looking for an experienced IT Specialist with strong Kubernetes expertise to manage, support, and optimize containerized applications and infrastructure. The ideal candidate will…
Added 3 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 3 hours ago
Robotics & Orbital Weld Specialist
Aecon
Cambridge, ON
Aecon delivers some of the most complex and impactful infrastructure projects - from transformative transportation networks to critical energy, industrial and nuclear programs. The projects…
Added 3 hours ago
Specialist, Software Engineering (SDET)
CMHC - SCHL
Toronto, ON · Ottawa, ON · Montreal, QC
Join the Business Solutions Engineering Team, in the Specialist, Software Engineering (SDET) position, where we are developing the next generation of software applications to enable CMHC to…
Added 4 hours ago
TC
ITSM Transition Anayst, Network Junior Engineer Jr
Tata Consultancy Services
Toronto, ON
- Full-time
…clients to transform themselves across the full AI stack, from infrastructure to…
Added 4 hours ago
AI
Application Specialist
Accuenergy Inc.
Toronto, ON · Greater Toronto Area, Canada
- Full-time
Prior contribution to AI / automation initiatives - workflow re-engineering, process automation, agent or RPA contribution.
Added 4 hours ago
CO
Job ID #31749: Application Support Specialist - EAM - REPOST
City Of Hamilton
Hamilton, ON
- Full-time
Job ID #31479: Application Support Specialist - EAM - REPOST
Added 4 hours ago
PC
Senior Technical Support Analyst
Parkland Corporation
Montreal, QC · Calgary, AB
- Full-time
Sunoco LP is a leading energy infrastructure and fuel distribution master limited partnership operating across 32 countries and territories in North America, the Greater Caribbean, and…
Added 4 hours ago
Energy Management Specialist
City of Mississauga
Mississauga, ON
Post-secondary diploma/degree in engineering, technology, or related field; or any combination of education and experience deemed equivalent. CEM, CMVP and LEED designations are an asset.
Added 7 hours ago
Y
Senior Windows Server Modernization Specialist
Yochana
Toronto, ON
- Full-time
Experienced Windows Infrastructure Professional to support the client's enterprise-wide Windows Server Modernization Program. The successful candidate will be responsible for planning,…
Added 8 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 10 hours ago
XI
Senior Data Engineer, Network Intelligence
Xplore Inc.
Canada
- Full-time
…building, maintaining, and optimizing data pipelines and supporting infrastructure on-prem - not just migrating workloads to the cloud. Your work directly underpins predictive analytics, ML…
Added 10 hours ago
M
DevOps Engineer
MMIST
Ottawa, ON
- Full-time
…commercial customers worldwide. We are currently seeking a DevOps Engineering Specialist to join our Ottawa based team, unlike many DevOps positions, this role is entirely focused on…
Added 10 hours ago
AS
Lead Data Engineer
AgileGrid Solutions
Canada
- Full-time
As a Senior Developer in Data Engineering within the Financial Crime and Regulatory Projects team at National Bank, you will serve as a Data Analytics Specialist responsible for designing,…
Added 12 hours ago
SC
Network and Systems Specialist
Stoakley-Stewart Consultants Ltd.
Barrie, ON
- Full-time
This organization is a highly specialized designer and builder of advanced automation systems used in complex manufacturing environments. Known for solving intricate production challenges,…
Added 1 day ago
NB
Senior Specialist Hybrid Telecom Platforms
National Bank of Canada
Montreal, QC
- Full-time
A career as a Senior Specialist – Hybrid Telecom Platforms in the Infrastructure and Operations team at National Bank means acting as an expert in connectivity and cloud environments. This…
Added 2 days ago
MO
Project Technician – Tier 3 Network & Infrastructure Specialist
MSP OPERATIONAL CORP
Guelph, ON · London, ON
- $90,000 to $100,000 CAD / year
As a Project Technician – Tier 3 Network & Infrastructure Specialist, you will play a senior hands-on role in the planning, design, and delivery of complex network and infrastructure…
Added 2 days ago
PA
Network and Systems Specialist
Prodomax Automation Ltd.
Barrie, ON
- Full-time
Prodomax Automation Ltd. is currently seeking a NETWORK AND SYSTEMS SPECIALIST to join our team.
Added 2 days ago
EM
Product Specialist, evertz.io
Evertz Microsystems Limited
Burlington, ON
- Full-time
As a Product Specialist, you'll be the technical bridge between our customers, product design, engineering, and operations - working hands-on with configuration, deployment, and cloud…
Added 2 days ago
AK
Accounting Specialist
Asahi Kasei
Port Colborne, ON · ABSCA – Port Colborne Plant
- Full-time
We are seeking an Accounting Specialist to be a part of a new plant start-up based in Port Colborne, Ontario. This position will be responsible for supporting all aspects of the accounts…

Yochana

Senior Windows Server Modernization Specialist

Toronto, ON, Canada

Full-time

Apply About employer

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Job details

Job type: Full-time
Apply by: Nov 4, 2026
Experience: 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

Position Name – Senior Windows Server Modernization Specialist

Type of hiring – Fulltime/Subcon

Location – Toronto, ON (Hybrid (2-3 days a week)

Job Description:

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 large-scale in-place upgrades from Windows Server 2016 to Windows Server 2025, including readiness assessments, implementation, validation, and post-upgrade support. Coordinate application testing and issue remediation, collaborate with enterprise teams, maintain technical and recovery documentation, and follow 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 enterprise-scale server upgrades or migrations. Candidates should also have virtualization and cloud infrastructure experience, familiarity with infrastructure management and ITSM tools, and knowledge of ITIL and enterprise change management; relevant Microsoft certifications and regulated-industry experience are assets.

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 Infrastructure
SCCM/MECM
SaltStack
Dynatrace
ServiceNow
IT Service Management
ITIL
Incident Management
Change Management
Problem Management
Release Management
Server Modernization
Server Upgrades
Server Migration
Automation
Patching
Troubleshooting
Production Support
Enterprise Infrastructure
Security Governance
Recovery Planning
Financial Services
MCSE

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