Training and Adoption Specialist

Convergence Networks•Winnipeg, MB

4d•CA$52,000 - CA$63,000•Hybrid

About The Position

The Training and Adoption Specialist is responsible for helping clients realize measurable value from their Microsoft Modern Work investments through effective user enablement, training delivery, adoption planning, and change support. This role focuses heavily on Microsoft 365 productivity tools, collaboration platforms, secure modern work practices, and Microsoft Copilot readiness and usage adoption. This individual serves as the bridge between technical solution deployment and real-world business outcomes. They ensure users, managers, and leadership teams understand how to use modern workplace technologies effectively, confidently, and safely. The Training and Adoption Specialist designs and delivers engaging learning experiences, drives user adoption strategies, supports change management efforts, and helps organizations maximize return on investment from Microsoft 365 and Copilot. The ideal candidate combines strong communication and facilitation skills with practical knowledge of Microsoft 365, Teams, SharePoint, OneDrive, Planner, Loop, Power Platform, and Microsoft Copilot. They are passionate about helping people embrace new ways of working and can translate technology capabilities into simple, relevant business value.

Requirements

Bachelor’s degree in Education, Business, Communications, Information Technology, Organizational Change, or a related field, or equivalent practical experience.
2–5+ years of experience in training, user enablement, adoption, learning and development, change management, or customer success in a technology-focused environment.
Experience delivering training on Microsoft 365 applications such as Teams, SharePoint, OneDrive, Outlook, Word, Excel, PowerPoint, and related productivity tools.
Experience supporting software adoption, digital transformation, collaboration platforms, or workplace technology initiatives.
Strong presentation, facilitation, communication, and instructional design skills.
Ability to explain technical and business concepts in clear, user-friendly language.
Strong organizational skills with the ability to manage multiple projects, audiences, and deadlines.

Responsibilities

Design, develop, and deliver end-user and administrator training sessions focused on Microsoft 365, including Microsoft Teams, SharePoint, OneDrive, Outlook, Planner, OneNote, Forms, Loop, and Copilot.
Facilitate live instructor-led training, workshops, webinars, lunch-and-learns, virtual sessions, and recorded learning modules for client organizations and internal teams.
Create learning paths tailored to different audiences, including leadership, department managers, frontline users, power users, champions, and administrators.
Adapt training content for varying levels of technical maturity and organizational readiness.
Develop user adoption strategies that support successful rollout of Microsoft 365 and Copilot capabilities across client environments.
Work with project teams, consultants, vCIOs, account managers, and technical specialists to ensure training and adoption activities are embedded into solution delivery.
Create adoption plans, communications plans, champion programs, user engagement campaigns, and post-deployment reinforcement activities.
Help clients identify barriers to adoption and build practical plans to improve engagement, confidence, usage, and business outcomes.
Support organizational change initiatives by reinforcing new work habits, collaboration models, document management practices, and AI-assisted workflows.
Help clients understand the people side of Copilot readiness, including user awareness, training requirements, safe AI usage expectations, and role-based business scenarios.
Develop Copilot training content around productivity improvement, meeting effectiveness, document creation, knowledge retrieval, summarization, and workflow acceleration.
Coach users on effective prompting practices, responsible AI use, validation of output, and appropriate governance-aligned behavior.
Partner with technical and security teams to ensure Copilot adoption aligns with data protection, compliance, and information governance expectations.
Measure and report on Copilot engagement, use case maturity, and practical value realization.
Develop high-quality training assets including slide decks, quick reference guides, playbooks, workshop materials, videos, FAQs, prompt libraries, job aids, adoption kits, and knowledge base content.
Maintain and improve reusable training and adoption materials that align with company standards, Microsoft best practices, and evolving platform capabilities.
Create role-based enablement materials that connect product features to real business processes and user pain points.
Continuously update training content as Microsoft 365 and Copilot features evolve.
Serve as a trusted advisor to clients on training, adoption, and end-user enablement for Modern Work initiatives.
Participate in client discovery sessions to understand business goals, workforce challenges, learning needs, and technology maturity.
Recommend practical learning and adoption approaches based on organizational size, culture, industry, and existing digital workplace maturity.
Support client success reviews, roadmap discussions, and value realization conversations by providing insight into user adoption progress and opportunities for improvement.
Define and track adoption metrics such as attendance, engagement, completion, feature usage, champion participation, user confidence, and business impact indicators.
Gather user feedback and training outcomes to continuously improve content quality and delivery approach.
Provide adoption reporting and recommendations to internal stakeholders and client leadership teams.
Identify trends, knowledge gaps, and opportunities to expand training offerings and packaged services.