Senior Help Desk Support & System Administrator

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.