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Added 20 hours ago
BT
Cloud Accountant
Baker Tilly Canada
Moncton, NB · Greater Moncton, NB
- Full-time
Utilizing technology and automation tools to improve workflow efficiency and accuracy
Added 1 day ago
BT
Cloud Accountant
Baker Tilly Canada
Moncton, NB · Greater Moncton, NB
- Full-time
Utilizing technology and automation tools to improve workflow efficiency and accuracy
Added 2 days ago
IT Systems Specialist
Opendoor
Toronto, ON
Administer endpoint, identity, and SaaS platforms, including Jamf, Intune, Okta, Google Workspace, and Microsoft 365.
Added 2 days ago
AI
Application Specialist
Accuenergy Inc.
Toronto, ON · Greater Toronto Area, Canada
- Full-time
Hands-on experience with CRM systems (Microsoft Dynamics 365 Sales Hub, Salesforce, Zoho, or comparable) and ERP systems (Microsoft Dynamics 365 Business Central or comparable).
Added 5 days ago
BD
Business Systems Support Specialist
Builder Direct Inc
Vancouver, BC
- Full-time
You will be trusted with meaningful work across ERP, integrations, ecommerce, CRM, and Microsoft 365. During acquisitions, you will assist with system discovery and transition tasks, but…
Added 5 days ago
E
Microsoft Copilot and AI Specialist
EllisDon
Mississauga, ON
- Full-time
3–5 years of relevant experience in Microsoft 365, enterprise technology, digital workplace, business analysis, technology adoption, automation, AI enablement or related field.
Added 5 days ago
H
Technical Support Specialist
Hays
Montreal, QC
- Contract
We are looking for a bilingual (French/English) Tech Connect Specialist to provide onsite IT support to employees in a fast-paced professional services environment. This role involves…
Added 5 days ago
LA
Senior CRM Specialist - Adobe Experience Cloud
Level Agency
Remote, Canada
- Full-time
- Remote
Experience with additional CRM and marketing automation platforms, such as Microsoft Dynamics 365, Klaviyo, or Braze
Added 7 days ago
Senior Help Desk Support & System Administrator
Strategic Group
Calgary, AB
Administer Microsoft Azure and Microsoft 365 cloud environments, including identity, access, licensing, and core services
Added 7 days ago
TC
Application Specialist
TDSB Community Services
Toronto, ON
- Full-time
Hands-on experience with CRM systems (Microsoft Dynamics 365 Sales Hub, Salesforce, Zoho, or comparable) and ERP systems (Microsoft Dynamics 365 Business Central or comparable).
Added 9 days ago
BT
Cloud Accountant
Baker Tilly Canada
Moncton, NB · Greater Moncton, NB
- Full-time
Utilizing technology and automation tools to improve workflow efficiency and accuracy
Added 9 days ago
L
AI Specialist/Spécialiste IA
Leyad
Montreal, QC
- Full-time
Familiarity with workflow automation, APIs, data integration, and business intelligence tools such as Power BI, Excel, or SQL.
Added 9 days ago
S
AI & Automation Solutions Specialist
Stantec
Toronto, ON
- Full-time
Join Buildings Digital Practice and help accelerate the adoption of artificial intelligence, automation, and digital solutions across the Buildings business. The AI & Automation Solutions…
Added 9 days ago
SL
Physical Security Intelligence and Investigations Specialist
Sun Life
Toronto, ON · Waterloo, ON · Sun Life Toronto One York
- Full-time
Proficiency with Microsoft 365, including Excel, SharePoint, PowerPoint, and Microsoft 365 Copilot; automation, reporting, or workflow experience is an asset.
Added 9 days ago
RM
Specialist Analytics & Business Support
Regional Municipality of Peel
Brampton, ON
- Other
Join our team as a Water/Wastewater (W/WW) Analytics and Business Support Specialist and leverage your skills to make a meaningful impact in Water and Wastewater Operations. Reporting to…
Added 9 days ago
CD
Business Systems Implementation Specialist (3 Month Contract)
CMHA Durham
Oshawa, ON
- Full-time
- Contract
Reporting to the Communications and Public Relations Lead, the Business Systems Implementation Specialist is responsible for planning, implementing, and optimizing technology systems and…
Added 11 days ago
A
Modern Workplace – Power Automate Specialist
Affinity
Vancouver, BC
- Contract
Our client is seeking a Senior Modern Workplace Consultant with deep expertise in Microsoft Power Platform and enterprise Microsoft 365 environments to support a critical business…
Added 12 days ago
RN
Workplace System Administrator
Riverside Natural Foods Ltd. (Home of MadeGood)
Toronto, ON
- Full-time
…peripherals, printer, RF scanner, VoIP phone, cell phones, tablets, Microsoft Office 365 applications, such as Outlook, Teams, OneDrive, etc., MFA, Adobe, DocuSign, Shared Drive, websites…
Added 12 days ago
Workplace System Administrator
Riverside Natural Foods Ltd.
Toronto, ON
…peripherals, printer, RF scanner, VoIP phone, cell phones, tablets, Microsoft Office 365 applications, such as Outlook, Teams, OneDrive, etc., MFA, Adobe, DocuSign, Shared Drive, websites…
Added 14 days ago
BT
IT Support Administrator
Beanfield Technologies Inc.
Toronto, ON
- $70,000 to $90,000 CAD / year
- Full-time
…while building readiness for a dual-platform environment using Microsoft Intune. The ideal candidate brings working knowledge of scripting and automation (Bash, PowerShell, or Python) to…
Added 15 days ago
CI
Microsoft Application Specialist – Contract
Compugen Inc
Orillia, ON
- Contract
This is a hands-on application and Microsoft systems role covering platform administration, workflow automation, application integration, business intelligence/data analysis and technology…
Added 16 days ago
CM
Workflow Automation & IT Support Specialist
Colonnade Management Inc.
Ottawa, ON
- Full-time
Reporting to the IT Manager, the Workflow Automation and IT Support Specialist designs, develops, deploys, and supports automated business workflows while providing hands-on IT support…
Added 16 days ago
E
Bilingual - Sr Talent Acquisition Specialist (French + English)
Epiroc
Mississauga, ON
- $95,912 to $126,870 CAD / year
- Full-time
Bilingual Senior HR Specialist – Talent Acquisition
Added 17 days ago
H
Technical Support Specialist
Hays
Montreal, QC
- Contract
We are looking for a bilingual (French/English) Tech Connect Specialist to provide onsite IT support to employees in a fast-paced professional services environment. This role involves…
Added 17 days ago
GT
Senior Specialist, Procurement Technology
Greater Toronto Airports Authority
Toronto, ON
- Full-time
Analyze performance data and stakeholder feedback to recommend system, workflow, automation, training and process improvements to Procurement leadership.

Strategic Group

Senior Help Desk Support & System Administrator

Calgary, AB, Canada

Apply About employer

Applications open in a new tab.

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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