SharePoint & Microsoft Teams Trainer

Insight Enterprises, Inc.; Calgary; Hybrid; CAD 65,000 - 90,000; Full time

Benefits offered by this job

Hybrid work model

Travel flexibility

Job summary

Insight Canada, a part of Insight Enterprises, Inc., is seeking a SharePoint & Teams Trainer to empower clients to adopt modern collaboration using SharePoint Online and Microsoft Teams. You will train diverse audiences, from end users to site owners, across virtual and in-person sessions within migration waves.

Based in Calgary with a hybrid work model, you will collaborate with cross-functional teams, including Organizational Change Management and eLearning, to ensure practical, role-based

Qualifications

• Experience delivering client-facing technical training or learning programs.
• Strong knowledge of SharePoint Online and Microsoft Teams sites, libraries, channels, permissions.
• Ability to facilitate both virtual and in-person sessions for diverse audiences.
• Ability to translate complex concepts into practical guidance.
• Excellent organization, presentation, and verbal communication skills.
• Willing to work regularly at the client’s Calgary office and travel as needed.

Responsibilities

• 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 to prepare client trainers for later migration waves.
• Adapt delivery approaches to audience roles, migration timing, and future-state processes.
• Prepare sessions by validating training environments, materials, and learner access.
• Collaborate with Change Management, eLearning, and project teams to ensure training aligns with objectives.
• Gather feedback and update materials and FAQs based on learner insights.

Skills

Client-facing training

Microsoft 365 learning

Training delivery

Public speaking

Organizational skills

Tools

SharePoint Online

Microsoft Teams

Office 365

Job description

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 modern 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 strong 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 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.