River East Transcona is a agile, caring, and innovative school division where our teachers and staff dedicate their days to providing students with the education, guidance, and services they need to learn and reach their fullest potential. We are the second-largest division in the province with nearly 19,000 students across 43 schools, supported by a dedicated team of more than 3,500 staff.

What We offer

Pension

Employee Purchase Plan

Health & Extended Benefits

On-site parking

Employee & Family Assistance Program

Health and Wellness Discounts

Bulletin No. 27OS-018

Administration Offices

Information Technology Department

Full-Time Position

35 hours per week

Term effective ASAP to October 22/2027

*Or one day prior to the return of the incumbent

Summary

Reporting to the Systems Support Manager, the SST: Microsoft 365 Specialist is responsible for administering and supporting RETSD’s cloud platform. Currently the school division utilizes services from Microsoft 365 to provide a collaborative environment for both staff and students; maintains a divisional web presence along with school websites, and an Intranet (The Hub).

Responsibilities Include

- Administer, support and secure Microsoft 365 services (i.e., Outlook Online, SharePoint Online, Project Online, OneDrive, Teams, etc.)
- Support client usage of Office 365 services, software, and apps
- Support Internet Information Services (IIS) based tools/utilities and websites
- Stay informed and notify relevant staff of new functionality and improvements coming to Microsoft 365




- Stay informed of new vulnerabilities relating to Microsoft 365 and work collaboratively with the IT Security lead
- Work collaboratively to plan, implement, and support a disaster recovery environment
- Liaise with support vendors
- Producing of publicly accessible Teams meetings; this may include after-hours sessions such as board meetings
- Develop and deliver training resources for the Microsoft 365 suite
- Resolve IT tickets; troubleshoot with team; research and development where needed
- Maintain required certification

Qualifications

- Education and experience:
- Bachelor’s degree (B.Sc.) or diploma in computer technology (preferred)
- Microsoft Certified Solutions Associate (MCSA) – Office 365 or Microsoft Certified Solutions Expert (MCSE) (preferred)
- Knowledge of Microsoft SharePoint and PowerShell with a strong understanding of Cloud based systems such as Microsoft 365. Microsoft SQL and Microsoft Project Server experience an asset
- Experience supporting webservers, back-end servers, Entra ID (Azure AD), and Active Directory
- Experience with supporting Windows client and server operating systems
- Windows client/server hardening (security vulnerability awareness) would be an asset
- Knowledge and experience planning and implementing enterprise migrations




- Experience with using Artificial Intelligence (AI) technologies such as Microsoft Copilot

Communications and interpersonal skills

- Excellent written and verbal communication skills
- Ability to work cooperatively and harmoniously with all organizational staff, management, and vendors
- Demonstrated professionalism and respect for privacy in dealing with sensitive and confidential employee and student information.

Organization and time management

- Demonstrated organizational and time management skills with the ability to multi-task and prioritize duties in a fast-paced environment
- Strong desire to stay informed of new initiatives
- High degree of initiative
- Strong problem-solving skills
- A valid MB driver’s license and a reliable vehicle is required
- Ability to climb a ladder is required
- Ability to lift/carry at least 20 pounds

Condition of Employment

Criminal Record Check (Including Vulnerable Sector Check): Must provide a clear and current Criminal Record Check with Vulnerable Sector Screening prior to starting employment.

Child Abuse Registry Check: Must provide a clear Manitoba Child Abuse Registry Check prior to employment.

The above statements reflect the general duties considered necessary to describe the principal functions of the position identified and shall not be construed as a detailed description of all work requirements that may be inherent to the position.

Deadline for applications: Monday, October 26, 2026 – 2:00 p.m.

Rate of Pay: $ 72,801 - $84,952 per annum

📌 Systems Support Technician (SST): Microsoft 365 Specialist (Winnipeg)
🏢 RIVER EAST TRANSCONA SCHOOL DIVISION
📍 Winnipeg