Bilingual Microsoft 365 Trainer

Special Olympics Canada; Toronto; On-site; CAD 68,000 - 80,000; Full time

Benefits offered by this job

3 weeks vacation

Extended health benefits

RRSP matching

Fitness benefit

Job summary

Special Olympics Canada is seeking a bilingual Microsoft 365 & Digital Adoption Specialist to boost digital skills and collaboration across the national organization. You will design practical training and deliver sessions for staff and Chapters, spanning Teams, SharePoint, OneDrive, Outlook, Word, Excel and PowerPoint.

The role covers hands-on administration, secure collaboration, and the adoption of Copilot, with emphasis on effective training and user support in a distributed, multi-site

Qualifications

• Fluency in written and spoken English and French is required.
• Demonstrated experience administering Microsoft 365 environments.
• 3-5 years experience supporting Microsoft 365 technologies, including Teams, SharePoint Online, Exchange Online, OneDrive, and Microsoft Entra ID.
• Proven ability to develop and deliver end-user training and practical technology guidance.
• Experience supporting and troubleshooting cloud-based collaboration platforms.

Responsibilities

• Develop and deliver Microsoft 365 training programs for National Office staff and Chapters.
• Facilitate instructor-led, virtual, and small-group training sessions on Microsoft Teams, SharePoint, OneDrive, Outlook, Forms, Power Automate, Copilot, and secure collaboration practices.
• Create learning materials, quick-reference guides, videos, FAQs, and knowledge base articles.
• Deliver Microsoft 365 onboarding sessions for new employees and support digital workplace orientation.
• Track training participation, adoption trends, and user feedback to improve future learning programs.
• Administer and support Microsoft 365 services including Teams, SharePoint Online, Exchange Online, OneDrive for Business, Entra ID, Intune, Forms, Copilot, etc.
• Provision and deprovision user accounts and support onboarding/offboarding.
• Manage licensing, shared mailboxes, distribution lists, and SharePoint permissions.
• Monitor service health and escalate issues as required.
• Maintain technical documentation and user resources.
• Provide Tier 2 support for Microsoft 365 apps and services.
• Troubleshoot authentication, sync, and access issues across devices.
• Identify recurring issues and propose permanent fixes.

Skills

Bilingual English and French

Training delivery

Microsoft 365 administration

User adoption programs

Education

Postsecondary degree in IT / CS or related field

Tools

Microsoft Teams

SharePoint Online

OneDrive

Exchange Online

Intune

Copilot

Power Automate

Microsoft Entra ID

Job description

Employment Terms:

Full-time, 12-month contract with potential for extension

Reports to:

Director, Digital Products & Technology

Position Summary

Special Olympics Canada (SOC) is seeking a bilingual Microsoft 365 & Digital Adoption Specialist / Trainerto strengthen digital skills, improve collaboration and support the effective use of Microsoft 365 across its national organisation.

The primary focus of this role is to develop and deliver practical, engaging training that helps employees and Chapters use Microsoft 365 confidently and effectively. Training will range from foundational and beginner-level instruction to intermediate guidance, adapting to different levels of technical knowledge and user needs.

Working across a distributed, multi-site environment, you will create training curricula, lead instructor‑led and virtual sessions, develop practical learning resources and provide hands‑on user support. You will help establish consistent Microsoft 365 knowledge and working practices across SOC, including best practices for Teams, SharePoint, OneDrive, Outlook, Word, Excel and PowerPoint.

Alongside training and user adoption, you will support Microsoft 365 administration, troubleshooting, secure collaboration, digital workplace improvements and the responsible adoption of tools such as Microsoft Copilot.

RESPONSIBILITIES:

• Develop and deliver Microsoft 365 training programs for National Office staff and Chapters.
• Facilitate instructor‑led, virtual, and small‑group training sessions on Microsoft Teams, SharePoint, OneDrive, Outlook, Forms, Power Automate, Copilot, and secure collaboration practices.
• Create learning materials, quick‑reference guides, videos, FAQs, and knowledge base articles.
• Deliver Microsoft 365 onboarding sessions for new employees and support digital workplace orientation.
• Track training participation, adoption trends, and user feedback to improve future learning programs.

Microsoft 365 Administration:

• Administer and support Microsoft 365 services including Microsoft Teams, SharePoint Online, Exchange Online, OneDrive for Business, Microsoft Entra ID, Microsoft Intune, Microsoft Forms, Power Automate, and Microsoft Copilot.
• Provision and deprovision user accounts and support employee onboarding and offboarding activities.
• Manage Microsoft 365 licensing, shared mailboxes, distribution lists, security groups, Teams memberships, and SharePoint permissions.
• Monitor Microsoft 365 service health and elevate issues to Microsoft or external partners as required.
• Maintain technical documentation, standards, procedures, and user support resources.

User Support and Service Delivery:

• Provide Tier 2 support for Microsoft 365 applications and services.
• Troubleshoot Outlook, Teams, OneDrive synchronization, SharePoint access, Intune, mobile device enrollment, and authentication issues.
• Resolve user access, permissions, collaboration, and file‑sharing issues in a timely and professional manner.
• Identify recurring issues and recommend permanent solutions to improve the user experience.
• Work with external vendors and Microsoft support where escalation or specialized expertise is required.
• Support the rollout, adoption, and optimization of Microsoft Copilot across SOC.
• Deliver Copilot awareness sessions, prompt‑writing workshops, and practical use‑case demonstrations.
• Assist departments in identifying opportunities to use Copilot responsibly to improve productivity and collaboration.
• Create guidance materials and best practices for responsible AI usage in alignment with SOC policies.
• Measure and report on Copilot adoption, user feedback, and business value realization.

Security, Compliance and Governance:

• Promote secure use of Microsoft 365 technologies and support cybersecurity awareness initiatives.
• Support the implementation and adoption of multi‑factor authentication, passwordless authentication, Conditional Access, device compliance standards, and secure file‑sharing practices.
• Assist with Data Loss Prevention, information protection, retention, and data governance initiatives.
• Support Microsoft Defender, Intune, and Microsoft Entra ID administration activities as assigned.
• Ensure users understand their role in protecting organizational information and using Microsoft 365 securely.

Digital Transformation and Continuous Improvement:

• Participate in SharePoint modernization, Teams governance, Copilot, automation, and business process improvement initiatives.
• Identify opportunities to reduce manual work using Microsoft 365 tools such as Forms, Lists, Power Automate, and Power Apps.
• Support chapter technology enablement and adoption across Canada.
• Assist with project planning, testing, deployment, change management, and post‑implementation support.
• Other duties as assigned.

QUALIFICATIONS:

• Fluency in written and spoken English and French is required.
• Postsecondary degree, diploma, or certificate in Information Technology, Computer Science, Business Technology, Adult Education, or a related field.
• Demonstrated experience administering Microsoft 365 environments.
• A minimum of 3-5 years experience supporting Microsoft 365 technologies, including Teams, SharePoint Online, Exchange Online, OneDrive, and Microsoft Entra ID.
• Proven ability to develop and deliver end‑user training, user adoption programs, and practical technology guidance.
• Experience supporting and troubleshooting cloud‑based collaboration platforms.
• Understanding of Microsoft 365 governance, security, privacy, and compliance best practices.
• Experience with Microsoft Intune, device management, and identity management is considered an asset.
• Knowledge of Microsoft Copilot and AI‑enabled productivity tools is considered a strong asset.
• Experience developing user guides, technical documentation, training materials, and self‑service support resources.
• Proven ability to explain technical concepts clearly to non‑technical audiences.
• Demonstrated ability to build collaborative relationships with Chapters and their IT service providers, coordinate across differing technical environments and priorities, and resolve issues through clear communication and stakeholder management.
• Exhibited problem‑solving ability in both structured and unstructured environments.
• Proven track record of managing multiple priorities with attention to timelines, quality, and user experience.
• Dependable judgement and decision‑making skills.
• Strong verbal and written communication skills including group presentations and facilitation.
• Comprehensive computer skills, including advanced proficiency in Microsoft 365 applications.
• A self‑directed and enthusiastic team player.
• Experience working in the non‑profit sector is considered an asset.

Preferred Certifications:

• Microsoft 365 Certified: Administrator Expert (MS-102).
• Microsoft 365 Fundamentals (MS-900).
• Microsoft Certified Trainer (MCT), considered an asset.
• Microsoft Teams Administrator Associate.
• Microsoft Security, Compliance, and Identity Fundamentals (SC-900).

WORKING CONDITIONS & PHYSICAL EFFORT:

• The position is based in SOC’s office in Toronto at 21 St. Clair Avenue East.
• Occasional travel may be required to attend meetings, Chapter events, conferences, and training sessions.
• Physical effort is minimal, though occasional lifting of boxes or equipment may be required, up to 25 lbs.

COMPENSATION & BENEFITS:

• $68,000 – $80,000 per year, based on experience, skills and qualifications
• 3 weeks’ vacation per year (pro‑rated to the contract duration)
• Eligible for SOC’s extended health benefits plan, including medical, dental, life, accident and long‑term disability coverage, RRSP matching, an employee assistance program and fitness benefit

About Special Olympics Canada

For more than 50 years, Special Olympics Canada has enriched the lives of Canadians with an intellectual disability through active participation in sport.