SharePoint & Microsoft Teams Trainer Requisition Number: 106303
SharePoint & Microsoft Teams Trainer
Location: This is a hybrid position based in Calgary, Alberta. The role requires regular in-person work at the client’s downtown Calgary office. Travel time to other client sites may vary depending on the engagement and location.
Insight at a Glance
14,000+ engaged teammates globally
$9.2 billion in revenue
Received 35+ industry and partner awards in the past year
$1.4M+ total charitable contributions in 2023 by Insight globally
Now is the time to bring your expertise to Insight. We are not just a tech company; we are a people-first company. We believe that by unlocking the power of people and technology, we can accelerate transformation and achieve extraordinary results. As a Fortune 500 Solutions Integrator with deep expertise in cloud, data, AI, cybersecurity, and intelligent edge, we guide organizations through complex digital decisions.
About the role We’re seeking a SharePoint & Microsoft Teams Trainer to join Insight Canada’s Adoption & Change Management team and collaborate closely with our Modern Workplace specialists. You will help clients build the skills and confidence required to adopt up-to-date collaboration practices using SharePoint Online and Microsoft Teams. Working as part of a multidisciplinary project team, you will facilitate engaging virtual and in-person training for end users, site owners, content owners, support teams, and train-the-trainer audiences. You will partner with Organizational Change Management, communications, eLearning, project management, and technical resources to ensure training is accurate, role-based, practical, and aligned with each migration wave. Projects may include cloud migrations, SharePoint information architecture initiatives, Microsoft Teams collaboration programs, and other Microsoft 365 adoption engagements.
As a Consultant on a SharePoint Migration project you will: Deliver engaging virtual and in-person SharePoint Online and Microsoft Teams training for end users, site owners, content owners, support teams, and other identified audiences
Facilitate train-the-trainer sessions that prepare client trainers to confidently deliver role-based learning during later migration waves
Adapt delivery approaches, demonstrations, exercises, and examples to audience roles, departmental needs, migration timing, and approved future-state ways of working
Prepare for each session by validating the training environment, demonstrations, materials, technical setup, learner access, and required scenarios




Partner with the Organizational Change Management Consultant to align training with change impacts, readiness findings, adoption objectives, and reinforcement needs
Partner with the eLearning Content Creator & Instructional Designer to review learning objectives, scripts, job aids, facilitator materials, knowledge checks, and role-based learning paths for accuracy and usability
Partner with the Communications & Deployment Coordinator to support training schedules, invitations, session logistics, attendance tracking, and delivery across migration waves
Gather learner feedback, identify recurring questions or knowledge gaps, and recommend updates to training materials, FAQs, support guidance, or reinforcement activities
Manage assigned training deliverables, preparation activities, delivery commitments, risks, and client communications while collaborating with project management and technical delivery resources
Be AmbITious: This opportunity is not just about what you do today but also about where you can go tomorrow. When you bring your hunger, heart, and harmony to Insight, your potential will be met with continuous opportunities to upskill, earn promotions, and elevate your career.
What we’re looking for Core requirements: You have experience delivering client-facing technical training, user enablement, or Microsoft 365 learning programs
You have robust working knowledge of SharePoint Online and Microsoft Teams, including sites, document libraries, channels, permissions, navigation, and collaborative file management
You’re comfortable facilitating virtual and in-person sessions for a range of audiences and creating an engaging, inclusive learning environment
You can confidently demonstrate technology, explain workflows, respond to learner questions, and adjust your delivery based on audience needs
You have experience using facilitator guides, participant materials, job aids, demonstrations, exercises, and knowledge checks to support learning
You can translate technical and governance concepts into clear, practical guidance that connects technology with day-to-day work
You have strong organization, preparation, presentation, facilitation, and verbal communication skills




You’re willing and able to work regularly at the client’s downtown Calgary office and travel based on the needs of the engagement
Standout candidates for the SharePoint Migration project will also bring: You have delivered SharePoint Online and Microsoft Teams training as part of a migration from network drives or email-based file sharing to modern cloud collaboration
You have experience training distinct personas, including end users, site owners, content owners, Help Desk teams, internal trainers, executives, or senior leaders
You have facilitated train-the-trainer programs and can coach internal trainers on delivery techniques, demonstrations, learner questions, and consistent messaging
You have experience tailoring training for multi-department or wave-based deployments and supporting reinforcement through office hours, coaching, refresher sessions, or user support
You understand Microsoft 365 governance and information management concepts and can explain permissions, ownership, document libraries, collaborative file practices, and support expectations in audience-friendly language
What you can expect We’re legendary for taking care of you, your family and to help you engage with your local community. We want you to enjoy a full, meaningful life and own your career at Insight.
Some of our benefits include: Freedom to work from another location—even an international destination—for up to 30 consecutive calendar days per year.
But what really sets us apart are our core values of Hunger, Heart, and Harmony, which guide everything we do, from building relationships with teammates, partners, and clients to making a positive impact in our communities.
Insight is an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, sexual orientation or any other characteristic protected by law.
When you apply, please tell us the pronouns you use and any reasonable adjustments you may need during the interview process.
At Insight, we celebrate diversity of skills and experience so even if you don’t feel like your skills are a perfect match - we still want to hear from you!
Insight is an equal prospect employer, and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability status, protected veteran status, sexual orientation or any other characteristic protected by law.

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📌 SharePoint & Microsoft Teams Trainer (Alberta)
🏢 Insight Enterprises
📍 Alberta