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Added 5 mins ago
R
Senior Procurement Analyst (Onsite)
RTX
Ottawa, ON
- Full-time
…and defense industry. With a comprehensive portfolio and deep technical expertise, we help customers meet the demands of the global market. Join us and help shape the future of aerospace…
Added 5 mins ago
Senior Manager Development, Treasury Technology
Scotiabank
Toronto, ON
The Senior Manager, Treasury Technology Delivery & Platforms is responsible for leading the technology strategy, delivery, and operational support of the Treasury Technology portfolio. This…
Added 5 mins ago
S
Senior Mechanical Engineer - Team Lead
Stantec
Edmonton, AB
- Full-time
In this role, you will draw on your strong technical knowledge, leadership capabilities, and extensive industry experience to lead the mechanical engineering team and deliver projects of…
Added 20 mins ago
A
Senior Civil Engineer - Part Time
AECOM
Winnipeg, MB
- $175,000 to $192,000 CAD / year
- Part-time
As AECOM continues to expand our Water business in Winnipeg, Manitoba, we're looking for an experienced Senior Civil Engineer to help lead the delivery of complex municipal wastewater…
Added 20 mins ago
LS
Senior Project Engineer - Facilities
Lauren Services
Kelowna, BC
- Contract
Lauren Services is seeking a Senior Project Engineer, Facilities (P.Eng.) to lead the technical delivery of complex brownfield and greenfield industrial facility projects. This role is…
Added 20 mins ago
LS
Senior Project Engineer - Pipeline
Lauren Services
Kelowna, BC
- Contract
Lauren Services is seeking a Senior Project Engineer, Pipelines (P.Eng.) to support and lead the technical execution of major pipeline projects across North America. This is a senior…
Added 20 mins ago
JA
Senior Project Lead Engineer
JR Automation
Montreal, QC · Saint-Laurent, QC
- Full-time
At Hitachi Energy, we’re shaping the future of power systems - making them smarter, safer, and more sustainable. As a Senior Project Lead Engineer, you’ll play a pivotal role in delivering…
Added 20 mins ago
JA
Technical Safety Specialist
JR Automation
Toronto, ON
- Full-time
Minimum 10 years of experience in a senior technical role in train control systems or automation in other industries such as aerospace, defense, automotive, medical or nuclear
Added 20 mins ago
PC
Senior Accountant
Pacific Coast Fruit Products Ltd.
Abbotsford, BC
- $85,000 to $95,000 CAD / year
- Full-time
The Senior Accountant plays a key role in supporting Pacific Coast Fruit Products’ financial operations by ensuring accurate, timely, and meaningful financial reporting. Reporting to the…
Added 20 mins ago
JA
Ingénieur principal de projet – HVDC/Senior Project Lead Engineer HVDC
JR Automation
Montreal, QC · Saint-Laurent, QC
- Full-time
Hitachi Energy's Grid Automation business is seeking a Senior Project Lead Engineer to take technical ownership of complex HVDC projects and tenders. In this role, you will coordinate…
Added 20 mins ago
JA
Sr. Bid & Proposal Specialist - Power Conversion Solutions
JR Automation
Toronto, ON
- Full-time
As a Senior Bid & Proposal Specialist, you will collaborate with sales, engineering, supply chain, and product teams to develop competitive, customer-focused bids that drive business growth…
Added 20 mins ago
JA
Senior Project Lead Engineer
JR Automation
Montreal, QC · Saint-Laurent, QC
- Full-time
At Hitachi Energy, we’re shaping the future of power systems - making them smarter, safer, and more sustainable. As a Senior Project Lead Engineer, you’ll play a pivotal role in delivering…
Added 20 mins ago
BC
Financial Analyst
BBA Consultants
Montreal, QC
- Full-time
As a financial analyst, you’ll work with consultants and senior advisors on client engagements and internal initiatives in Canada and internationally. You’ll also build and review financial…
Added 20 mins ago
BR
Senior Product Manager
BITS Recruiting
Toronto, ON
- Contract
Our client is seeking a Senior Product Manager to support its Enterprise Pub/Sub Applications Team. This role will lead product strategy, roadmap development, and prioritization of…
Added 35 mins ago
TC
Health & Safety Manager
Trinity Consultants Canada
Terrace, BC
- Full-time
Lead, mentor, and support safety personnel across Canadian operations, providing strategic direction, performance management, and technical oversight while ensuring consistent…
Added 35 mins ago
M
Senior IT Procurement Specialist
Medavie
Moncton, NB · NB · NL · NS · ON · PE · MBC NB Head Office Moncton
- Full-time
Demonstrated continuous improvement mindset (process, procurement methodologies, operating model) and ability to lead change initiatives
Added 35 mins ago
PL
Project Manager - PL#72904
Peter Lucas
Prince George, BC
- $110,000 to $130,000 CAD / year
- Full-time
…The successful candidate will demonstrate strong leadership, technical knowledge, and project management expertise while promoting a culture of safety, accountability, and continuous…
Added 36 mins ago
AC
Conventional Signaling Delivery Director – Track Team
Accenture Construct
Toronto, ON
- Full-time
Lead delivery of conventional signalling works within the Track team across corridors
Added 36 mins ago
E
Contrôleur financier / Contrôleuse financière
Exceleris
Brossard, QC
- Full-time
Lead, supervise and develop the accounting team.
Added 36 mins ago
AG
Senior SAP S/4HANA Basis Consultant
Addmore Group
Oshawa, ON
- Full-time
The Basis consultant is responsible for the technical integrity, performance and security of the SAP landscape. This role drives the installation, configuration, upgrading, and maintenance…
Added 50 mins ago
C
Senior Consultant, Control Optimization & Analytics
CIBC
Toronto, ON
- Full-time
Reporting to Director, Advanced Analytics, Strategy and Transformation, you will be a senior contributor for developing and delivering on the Advanced Analytics team’s technical solution…
Added 50 mins ago
T
Lead Mil-Ka Senior System Engineering Specialist
Telesat
Ottawa, ON
- Full-time
Within the System Engineering team, lead the technical coordination needed to adapt Lightspeed’s low Earth orbit constellation and associated ground infrastructure for military Ka-band…
Added 50 mins ago
C
Sr. Consultant, Data Platform DevOps
CIBC
Toronto, ON
- Full-time
…critical business and technology priorities across CIBC. As a Senior Consultant, Data Platform DevOps, you'll lead the development and enhancement of DevOps practices for our data platform,…
Added 50 mins ago
C
Program Advisory, Consulting & Execution, Senior Vice President
Citi
Mississauga, ON
- Full-time
Lead the scoping, design, and execution of target operating model and process transformation initiatives; partner with senior business, operations, and functional leadership to establish…
Added 50 mins ago
C
Senior Consultant, Employee Technology Services
CIBC
Toronto, ON
- Full-time
…experiences through thoughtful technology support strategies. As a Senior Consultant, Employee Technology Services, you'll provide leadership and subject matter expertise across automation…

Closed listing

Yochana

Senior Windows Server Modernization Specialist

Toronto, ON, Canada

Full-time

This opening has closed.

The original listing is kept below for reference.

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About employer

Job details

Job type: Full-time
Closing date: 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

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Original job description

Archived listing. The details below describe a past opening.

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.

About employer

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

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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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