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.
- Creative: 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 netwo

📌 Senior Help Desk Support (Calgary)
🏢 Strategic Group
📍 Calgary