Digital Skills Facilitator

*This will be a Remote / Hybrid or in-person position; periodic travel to Victoria, BC will be required.*

For over 25 years Smart Dolphins has been helping businesses on Vancouver Island and beyond thrive through technology with exceptional IT solutions and genuine care.

If you're looking for a team that values curiosity, embraces innovation, and knows how to have fun along the way, you've found it. You'll join our Pod: a group of passionate, caring, and clever Dolphins who are dedicated to shaping the future of work and making a real splash for our clients and in the community

Some of our notable awards:

• Great Place to Work in Canada: 2019–2025

• VIATEC Employer of the Year: Winner & Nominee (2025)

About the Role

We are seeking an experienced Digital Skills Facilitator & Trainer to deliver high-quality Microsoft 365 training and support services to our clients. As part of our consulting team, you'll work with diverse organizations to build digital capability, improve productivity, and maximize the value of their Microsoft ecosystem investments.

This role offers variety and flexibility, you'll work with multiple clients across sectors, adapting your facilitation style to meet different organizational cultures, skill levels, and business needs. You'll be the trusted guide who transforms confusion into confidence and helps teams unlock the full potential of their Microsoft tools.

Key Responsibilities

Client Training & Facilitation

• Deliver engaging, interactive training sessions on Microsoft 365 tools (Teams, SharePoint, OneDrive, OneNote, Power Automate, Planner, etc.) tailored to client needs

• Facilitate AI readiness workshops to help clients understand and prepare for adoption (e.g. Microsoft Copilot)

• Conduct skills assessments to understand client teams' current capabilities and learning priorities

• Assist in designing customized workshops and learning programs that address specific client workflows and pain points

• Facilitate both group training sessions and individualized coaching for key stakeholders

• Provide follow-up support to reinforce learning and troubleshoot adoption challenges

Curriculum & Resource Development

• Assist in creating client-specific training materials, quick reference guides, and job aids

• Assist in creating AI readiness assessment tools and adoption roadmaps for client organizations

• Develop scalable learning resources that can be adapted across different client contexts

• Stay current with Microsoft 365 updates and translate new features into training opportunities

• Assist in building reusable training modules while maintaining flexibility for client customization

Client Relationship Management

• Serve as a knowledgeable, approachable partner who builds trust and rapport with client teams

• Communicate clearly with client leadership about training goals, progress, and outcomes

• Gather feedback to continuously improve training effectiveness and client satisfaction

• Identify opportunities for expanded engagement or additional training needs

• Collaborate with our internal team to ensure seamless client service delivery

Change Enablement & AI Adoption

• Support clients through digital transformation by addressing both technical skills and mindset shifts

• Champion adoption by demonstrating real-world applications that solve client challenges

• Build confidence among hesitant users through patient, judgment-free facilitation

• Help clients establish internal champions and sustainable support structures

• Address common concerns and questions about AI in the workplace with clarity and practical guidance

Qualifications

Required:

• Deep Microsoft 365 expertise: 5+ years of hands-on experience using the full Microsoft ecosystem in professional settings

• AI awareness: Understanding of AI capabilities in productivity tools and ability to explain AI concepts to non-technical audiences

• Training/facilitation experience: Proven track record delivering technology training to adult learners in professional environments

• Client-facing skills: Strong interpersonal abilities, professional presence, and comfort working with diverse organizational cultures

• Adaptability: Ability to quickly understand different business contexts and customize training approaches accordingly

• Communication skills: Exceptional ability to explain technical concepts in accessible, jargon-free language

• Self-directed: Comfortable working independently, managing your schedule, and coordinating with multiple clients

Preferred:

• Microsoft certification (Microsoft 365 Certified: Fundamentals, Associate, or Expert level)

• Experience with AI productivity tools (Microsoft Copilot, ChatGPT, Claude, etc.)

• Consulting or professional services background

• Experience across multiple sectors (nonprofit, healthcare, corporate, government, etc.)

• Instructional design or adult education background

• Familiarity with change management methodologies

• Knowledge of accessibility standards and inclusive technology practices

• Experience with Microsoft Power Platform (Power Apps, Power Automate, Power BI)

• Understanding of AI ethics, governance, and responsible AI principles

Time Commitment & Structure

• Client sessions typically scheduled during business hours (some flexibility for time zones)

• Mix of on-site and virtual delivery depending on client needs and location

• Preparation time for customizing materials and planning sessions

• Some availability for client communication outside of scheduled training blocks

What Success Looks Like

• High client satisfaction scores and positive testimonials about training quality

• Demonstrable improvement in client teams' Microsoft 365 adoption and confidence

• Clients successfully applying learned skills to their actual work processes

• Repeat engagements and referrals from satisfied clients

• Seamless collaboration with our internal team and alignment with client objectives

• Efficient, professional delivery that reflects well on our consulting brand