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Added 16 mins ago
AG
Intermediate Designer
Adelphi Group
Toronto, ON
- Full-time
…Designer will take on briefs/work assigned by the Marketing Project Manager or Design Director and is relied on by the Marketing team to design and produce a variety of projects. They will…
Added 1 hour ago
Senior Manager of Operations
New Age Services Inc.
Calgary, AB
Post-secondary education in Business Administration, Operations Management, Information Technology, Project Management, Public Administration, or related discipline. Equivalent combinations…
Added 2 hours ago
PC
Risk Modelling Services, Actuarial P&C Director (Bilingual FR/EN)
PwC Canada
Toronto, ON
- Full-time
…You’ll provide advice covering solvency, economic capital, risk management, mergers and acquisitions, company restructuring, financial modelling, new legislation, and the efficiency of…
Added 4 hours ago
R|
Animal Resources Division Manager – Montreal General Hospital Site
RI-MUHC | Research Institute of the MUHC | #rimuhc
Montreal, QC
- Full-time
Under the general supervision of the Director, Animal Resources Division (ARD), the incumbent is responsible for the management of the research animal facilities at the Montreal General…
Added 4 hours ago
R|
Project Manager, Capture and Optimization of Research Data (CORD) Platform
RI-MUHC | Research Institute of the MUHC | #rimuhc
Montreal, QC
- Full-time
The Research Institute of the MUHC is seeking an interim Project Manager to join the Capture and Optimization of Research Data (CORD) platform of the Centre for Outcomes Research and…
Added 4 hours ago
R|
Research Assistant - Public Engagement
RI-MUHC | Research Institute of the MUHC | #rimuhc
Montreal, QC
- Full-time
You will report directly to the Director (Dr. Emily McDonald), with direction also provided by the Assistant Director (Camille Gagnon).
Added 4 hours ago
HT
Trade Compliance Program Manager
Husky Technologies
Bolton, ON
- Full-time
As the Global Trade Compliance Program Manager, you will report to the Director, Global Trade Compliance & Customs and serve as the program lead for enterprise-wide trade compliance…
Added 4 hours ago
BA
Project Manager
Branch Audiovisual
Toronto, ON
- Full-time
The Project Manager will report directly to the Director, Project Management. Secondary accountability will be to the other management team members, employees, and customers of the company.
Added 5 hours ago
BC
Quality and Patient Safety Consultant
Brant Community Healthcare System
Brantford, ON
- Full-time
Certification in Patient Safety or completion of a Project Management Program considered an asset
Added 5 hours ago
BC
Director, Communications and Engagement – Redevelopment Projects
Brant Community Healthcare System
Brantford, ON
- Full-time
…President, Strategy, Quality, Risk and Communications, the Director, Communications and Engagement – Redevelopment Projects provides strategic direction for all communications, interest…
Added 6 hours ago
UO
Development Officer
University of Victoria
Victoria, BC
- Full-time
Proven experience in project management within a large, complex institution is an asset
Added 10 hours ago
E
Civil Engineer (Mining)
EXP
Brampton, ON
- Full-time
Assist the Director of Engineering, civil Engineer and EITs with the delivery of project requirements as they relate to scope, cost and schedule.
Added 10 hours ago
RM
M.L.T. Charge - Quality
Ross Memorial Hospital
Kawartha Lakes, ON · Lindsay, ON
- Full-time
Reporting to the a Integrated Director Laboratory Services, is responsible for the implementation, maintenance and improvement of the quality management system and Hospital Point of Care…
Added 10 hours ago
CC
Director, Intake & Investigations
Canadian College of Health Leaders - Northwestern Ontario Chapter
Vancouver, BC
- Full-time
Reporting to the Executive Director, Professional Conduct Review (ED, PCR), the Director, Intake & Investigations
Added 10 hours ago
GI
Millwork Engineer / CNC Programmer
Giffin Interior
Engineer, BC
- Full-time
Collaborate closely with Drafting, Engineering, Production, Project Management, and Purchasing.
Added 10 hours ago
HT
Trade Compliance Program Manager
Husky Technologies
Bolton, ON
- Full-time
As the Global Trade Compliance Program Manager, you will report to the Director, Global Trade Compliance & Customs and serve as the program lead for enterprise-wide trade compliance…
Added 13 hours ago
Senior Help Desk Support & System Administrator
Strategic Group
Calgary, AB
Reporting to the Director, Information Technology, this role plays a key part in maintaining operational continuity, administering Windows Server and Azure environments, supporting business…
Added 14 hours ago
FH
Engineering Manager
Fairmont Hotels & Resorts
Vancouver, BC
- Full-time
…most historic and celebrated luxury hotels. Reporting to the Director and Assistant Director of Engineering, you will help lead the daily operations of the Engineering Department, ensuring…
Added 15 hours ago
UO
Teaching and Learning Officer
University of Victoria
Victoria, BC
- Full-time
Reporting to the Director, Business Operations, the Teaching and Learning Officer serves as the central coordinator for Gustavson’s teaching and learning portfolio and is the primary…
Added 15 hours ago
N
Materials & Qualification Specialist
Nexans
Markham, ON
- Full-time
As a Materials & Qualification Specialist, you will report directly to the Engineering and Technical Director in our Engineering team.
Added 15 hours ago
MT
Bilingual Manager, Instructional Design
McCarthy Tétrault LLP
Montreal, QC
- Full-time
With the support of the MT Academy Director, designing, developing, overseeing effective delivery of, and continuously improving national Leadership and Business Development programs for…
Added 16 hours ago
R|
Project Manager, Capture and Optimization of Research Data (CORD) Platform
RI-MUHC | Research Institute of the MUHC | #rimuhc
Montreal, QC
- Full-time
The Research Institute of the MUHC is seeking an interim Project Manager to join the Capture and Optimization of Research Data (CORD) platform of the Centre for Outcomes Research and…
Added 16 hours ago
R|
Research Assistant - Public Engagement
RI-MUHC | Research Institute of the MUHC | #rimuhc
Montreal, QC
- Full-time
You will report directly to the Director (Dr. Emily McDonald), with direction also provided by the Assistant Director (Camille Gagnon).
Added 16 hours ago
R|
Animal Resources Division Manager – Montreal General Hospital Site
RI-MUHC | Research Institute of the MUHC | #rimuhc
Montreal, QC
- Full-time
Under the general supervision of the Director, Animal Resources Division (ARD), the incumbent is responsible for the management of the research animal facilities at the Montreal General…
Added 16 hours ago
HT
Trade Compliance Program Manager
Husky Technologies
Bolton, ON
- Full-time
As the Global Trade Compliance Program Manager, you will report to the Director, Global Trade Compliance & Customs and serve as the program lead for enterprise-wide trade compliance…

Strategic Group

Senior Help Desk Support & System Administrator

Calgary, AB, Canada

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Job details

Posting language: English
Posted: Oct 14, 2026

Original job description

Senior Help Desk Support & System Administrator

Join Our Team at Strategic Group

Ready to grow your career with one of Canada’s leading privately held real estate companies? At Strategic Group, we create spaces where people, businesses, and communities thrive.

About Us

At Strategic Group, our purpose is simple: Learning. Growing. Having Fun. We bring this ethos to life by innovatively envisioning, creating, owning, and operating real estate that transforms spaces and redefines possibilities.

As a fully integrated real estate company, we specialize in owning, managing, leasing, developing, and re-developing properties. Our entrepreneurial spirit and innovative thinking have made us a Canadian industry leader in office-to-residential conversions, completing more successful conversions than anyone else in the country. This focus is a driving force in our development business and reflects our commitment to creatively reimagining what’s possible.

Our real estate portfolio spans high-end residential developments and commercial properties. Beyond real estate, our business interests include corporate finance and other industries, enabling us to deliver diverse and impactful solutions for our tenants, partners, and communities.

Guided by our mantra, “Creating value others can’t, by seeing what others don’t,”we take pride in crafting unique solutions that leave a lasting legacy.

Our Values

At Strategic Group, our values guide everything we do:

Team Player: We foster a supportive, accountable, and drama-free workplace where integrity and respect guide every interaction.
Innovative: Creativity and unconventional thinking are at the heart of what we do, helping us uncover opportunities others might miss.
Growth-Oriented: We are tenacious and passionate, thriving on challenges and embracing learning as we pursue new opportunities.
Optimistic: With a positive mindset and solution-oriented approach, we tackle obstacles as opportunities to learn, grow, and have fun.

If you’re ready to join a team that thinks boldly, acts innovatively, and works collaboratively, we’d love to hear from you!

Position Overview

The Senior Help Desk Support & System Administrator is responsible for delivering advanced technical support while owning the day-to-day administration of the organization’s core server, cloud, and business systems. This dual role combines hands-on end-user support and escalation with the configuration, maintenance, security, and reliability of on-premises and cloud infrastructure, ensuring systems, devices, and users are supported efficiently and effectively.

Reporting to the Director, Information Technology, this role plays a key part in maintaining operational continuity, administering Windows Server and Azure environments, supporting business applications such as Sage 50, and driving automation and process improvement across all locations.

Key Responsibilities

Advanced Technical Support & Escalation

Provide advanced desk-side and remote support for complex hardware, software, and network issues
Diagnose recurring issues and implement long-term solutions to improve system stability
Support system performance optimization and troubleshooting across environments

User Support & Service Delivery

Deliver high-quality technical support to Team Members across all levels of the organization
Support onboarding and offboarding processes, including system setup, access, and equipment provisioning
Manage user accounts, permissions, and system access controls
Ensure clear, professional communication and a strong customer service experience

Device & Systems Management

Oversee setup, configuration, and support of desktops, laptops, mobile devices, and peripherals
Support and manage mobile device environments and communication tools
Assist in administration of internal systems, including directories, collaboration tools, and shared platforms
Ensure consistency and reliability of IT systems across locations

System Administration & Infrastructure

Administer, maintain, and troubleshoot Windows Server environments, including Active Directory, Group Policy, DNS, DHCP, file and print services, and patch management
Administer Microsoft Azure and Microsoft 365 cloud environments, including identity, access, licensing, and core services
Provide application support and administration for Sage 50 accounting software, including user support, updates, and coordination with Finance
Monitor system health, performance, backups, and disaster recovery, ensuring availability and data integrity across on-premises and cloud systems
Support and administer network infrastructure and endpoint security in line with IT security policies and best practices

Automation & Process Improvement

Design, build, and maintain automated workflows using Power Automate to streamline IT and business processes
Identify manual or repetitive tasks and implement automation to improve efficiency, accuracy, and consistency
Document and maintain automated processes, integrations, and supporting runbooks

IT Operations & Coordination

Coordinate IT requests, ensuring appropriate prioritization and escalation to the appropriate support groups and specialist resources
Participate in a rotating on-call schedule to provide after-hours support for critical systems and incidents
Oversee IT desk moves, equipment deployments, and workspace setups
Maintain and monitor IT inventory, ensuring accurate tracking of assets
Support administration and optimization of internal systems, including phone systems and user directories

Project Leadership & Continuous Improvement

Lead or support implementation of IT projects, system upgrades, and technology rollouts
Identify opportunities to improve IT processes, workflows, and service delivery
Develop and maintain documentation, procedures, and knowledge-sharing resources
Support standardization of IT practices across the organization

Cross-Functional Collaboration & Mentorship

Collaborate with internal teams and external vendors to resolve issues and support initiatives
Support IT needs across multiple locations, including on-site troubleshooting when required
Contribute to a collaborative and high-performing IT team environment

Qualifications

Hands-on experience administering Windows Server (Active Directory, Group Policy, DNS/DHCP, file services)
Experience administering Microsoft Azure and Microsoft 365 cloud environments
Experience supporting Sage 50 accounting software
Experience building and maintaining workflows with Power Automate
Strong working knowledge of desktop/laptop hardware, Windows client operating systems, and networking fundamentals
Basic Yardi support experience is considered a benefit but is not required
Availability to participate in a rotating on-call schedule for after-hours support is required
Advanced technical troubleshooting and problem-solving capability
Strong customer service and communication skills

Our Culture & Benefits

At Strategic Group, we’re committed to helping you build a career you’re excited about. If you’re passionate about working with a dynamic, motivated team in a fast-paced environment, please submit your resume and cover letter today, and join us in making an impact.

We are proud to be an equal opportunity employer and celebrate diversity in all its forms. Our inclusive workplace ensures every employee feels valued and empowered to bring their best self to work.

As part of the Strategic Group team, you’ll enjoy a competitive compensation package, including an extended health and dental benefits plan, company events, flex days, and more.

This position is based in Calgary, Alberta. Applicants must be located in Calgary or the surrounding area.

We appreciate all applications, however, only candidates selected for an interview will be contacted.

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More about this job

Responsibilities

The Senior Help Desk Support & System Administrator provides advanced technical support to end-users while managing the organization's core server, cloud, and business systems. This role also focuses on driving automation, maintaining system security, and ensuring operational continuity across all locations.

Requirements

Candidates must have hands-on experience with Windows Server, Azure, Microsoft 365, and Sage 50 accounting software. Strong technical troubleshooting skills and the ability to participate in an after-hours on-call rotation are required.

Skills

Windows Server administration
Active Directory
Azure
Microsoft 365
Sage 50
Power Automate
Technical support
System administration
Network infrastructure
Group Policy
DNS
DHCP
Troubleshooting
Hardware support
Automation
Disaster recovery

Benefits

Extended health and dental benefits plan
Company events
Flex days

Visa sponsorship

Not detected in the job text

Keywords

Windows Server
Active Directory
Azure
Microsoft 365
Sage 50
Power Automate
System Administration
Help Desk
Group Policy
DNS
DHCP
Network Infrastructure
Automation
Disaster Recovery
IT Operations
Hardware Support
Identity Management
Access Control
Patch Management
Endpoint Security
Real Estate
Technical Support
Troubleshooting
Asset Management
Workflow Automation

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