Microsoft 365 Productivity Trainer

M365 updates, training impacts & escalation support 15% Stay current on Microsoft 365 releases, updates and changes, identify training impacts, coordinate with product/technical teams, and route issues or escalations appropriately. Change enablement, communications & communities 10% Support adoption campaigns, Viva Engage/community responses, champion-style enablement, stakeholder communication, and change management activities that move users from awareness to confident use.

KAYGEN is an emerging leader in providing top talent for technology-based staffing services. We specialize in providing high-volume contingent staffing, direct hire staffing and project-based solutions to companies worldwide ranging from startups to Fortune 500 and Managed Service Providers (MSP) across a wide variety of industries.


Job Description:
Role Overview

• Digital Dojo is seeking a hands-on Microsoft 365 trainer and adoption consultant to help guide TMNA’s workforce to use collaboration and productivity tools with confidence. The role focuses on practical enablement for Teams, SharePoint, OneDrive, and related M365 productivity topics, with general Copilot skills included as the Microsoft 365 experience evolves.

Key Responsibilities:

• Approximate workload percentages are estimates. Actual balance will flex based on Digital Dojo priorities, class demand, new M365 releases, and consultation volume.
• Responsibility area Approx. workload What this includes
• Training design, refresh & live facilitation 30% Design, update, and deliver live virtual classes and workshops across M365 productivity topics. Facilitate demos, Q&A, follow-up resources, and recordings where appropriate.
• 1:1 / team consultation & adoption coaching 30% Provide practical coaching through individual consults, small-group support, and written guidance. Help users translate tool capabilities into better work habits, collaboration patterns, and team workflows. For example, advise teams on SharePoint site ownership/maintenance, design, modern web parts, permissions concepts, and document collaboration, file sharing, external collaboration, and adoption practices across the M365 cloud.
• M365 updates, training impacts & escalation support 15% Stay current on Microsoft 365 releases, updates and changes, identify training impacts, coordinate with product/technical teams, and route issues or escalations appropriately.
• Learning content, job aids & resource curation 10% Create and maintain facilitator guides, quick reference guides, one-pagers, short demos, self-service resources, and curated links from internal and external sources.
• Change enablement, communications & communities 10% Support adoption campaigns, Viva Engage/community responses, champion-style enablement, stakeholder communication, and change management activities that move users from awareness to confident use.
• Program coordination, schedule support & reporting 5% Maintain class schedules, registration details, Planner tasks, feedback summaries, attendance metrics, and team updates.
• Primary Training and Consultation Topics

The person in this role should have expertise in the following areas:
Teams: Core Teams collaboration, chat and channels, meeting best practices, conference room technology, meeting notes/recaps, practical meeting facilitation, breakout rooms, hybrid meetings.
SharePoint: Modern site design, site creation from scratch, web parts, design tips, document libraries, permissions and site management/maintenance, file collaboration, videos in SharePoint, and practical site-owner guidance.
OneDrive & cloud files: Personal cloud workspace, file storage, sharing, desktop sync and shortcuts, co-authoring, organizing files across Teams, SharePoint, and OneDrive.
M365 productivity workflows: Searching across the M365 cloud, organization/sharing/collaborating patterns across the Microsoft ecosystem, file lifecycle best practices, and external sharing/collaboration.
Planner, Loop, Outlook, Bookings, Windows 11: Task and project planning, collaborative ideation, calendar/meeting productivity, appointment scheduling, and relevant Windows 11 productivity features.
Copilot awareness as a complement: General Copilot learning and responsible tool-choice guidance as it connects to the Microsoft 365 ecosystem.

Required Skills and Experience
Education / background

• Bachelor’s degree or equivalent experience in information systems, business, technology enablement, or a related field.
• 5+ years of experience training, supporting, consulting, or enabling end users on Microsoft 365 collaboration and productivity tools in a corporate environment.
• Microsoft 365 expertise
• Deep practical knowledge of Teams, SharePoint Online, OneDrive, and file collaboration across the Microsoft 365 ecosystem.
• Deep experience working in the M365 ecosystem, with comfort explaining and coaching about the following collaboration and productivity apps: Planner, Loop, Outlook, Bookings, and others as needed.
• Working knowledge of Copilot Chat (Basic) and M365 Copilot (Premium), especially where they intersect with meetings, files, and productivity workflows.
• Training, consulting, and communication
• Strong facilitation and public speaking skills, including live demos, Q&A, and practical examples for non-technical audiences in virtual, hybrid, and in-person settings.
• Ability to design clear learning materials, quick reference guides, class decks, short demos, and other reusable resources.
• Consultative mindset, with the ability to listen, diagnose user needs, recommend practical next steps, and coach individuals and teams to adopt new ways of working.
• Strong written communication, stakeholder management, organization, follow-through, and comfort managing multiple concurrent requests.
• Preferred Skills and Experience
• Instructional design, eLearning, video creation, or content development experience.
• Formal change management, adoption, or Prosci/ADKAR experience.
• Experience supporting champions, communities of practice, Viva Engage communities, and/or other peer learning programs.
• Experience in a large enterprise environment with multiple affiliates, business units, and stakeholder groups.
• Microsoft certifications or equivalent practical experience in Microsoft 365, Teams, SharePoint, OneDrive, or modern workplace adoption.
• Vendor, partner, or product team coordination experience, especially around enablement content, roadmap awareness, training vendors, or Microsoft programs.
• Success Measures
• Training is current, practical, and aligned to the needs of TMNA users and business teams.
• Learners and stakeholders report increased confidence using Teams, SharePoint, OneDrive, and modern ways of working across M365 collaboration and productivity tools.
• Business teams are better equipped to own and maintain SharePoint sites and collaboration spaces.
• Digital Dojo has reusable content, job aids, and consultation patterns that scale beyond one-off support.
• Adoption support is connected to change management, communications, community learning, and measurable feedback.

Requirements:
Looking for someone who has 5+ years of experience training, supporting, consulting, or enabling end users on Microsoft 365 collaboration and productivity tools in a corporate environment.

Key Responsibilities:

• Approximate workload percentages are estimates. Actual balance will flex based on Digital Dojo priorities, class demand, new M365 releases, and consultation volume.
• Responsibility area Approx. workload What this includes
• Training design, refresh & live facilitation 30% Design, update, and deliver live virtual classes and workshops across M365 productivity topics. Facilitate demos, Q&A, follow-up resources, and recordings where appropriate.
• 1:1 / team consultation & adoption coaching 30% Provide practical coaching through individual consults, small-group support, and written guidance. Help users translate tool capabilities into better work habits, collaboration patterns, and team workflows. For example, advise teams on SharePoint site ownership/maintenance, design, modern web parts, permissions concepts, and document collaboration, file sharing, external collaboration, and adoption practices across the M365 cloud.
• M365 updates, training impacts & escalation support 15% Stay current on Microsoft 365 releases, updates and changes, identify training impacts, coordinate with product/technical teams, and route issues or escalations appropriately.
• Learning content, job aids & resource curation 10% Create and maintain facilitator guides, quick reference guides, one-pagers, short demos, self-service resources, and curated links from internal and external sources.
• Change enablement, communications & communities 10% Support adoption campaigns, Viva Engage/community responses, champion-style enablement, stakeholder communication, and change management activities that move users from awareness to confident use.
• Program coordination, schedule support & reporting 5% Maintain class schedules, registration details, Planner tasks, feedback summaries, attendance metrics, and team updates.

• Referrals
• Family and Wellness benefits
• Continuous Growth and Career Development