Freelance Facilitator

Greater Toronto Area • In-Person and Virtual

We’re looking for freelance facilitators who love being in front of a room, are genuinely curious about AI, and get excited helping other people discover what these tools can actually do.

At Overlap, we deliver Relational AI Learning Labs: interactive, hands-on sessions that help people explore more thoughtful, practical, and human-centred ways of working with AI. These are not passive, lecture-style sessions. Participants come ready to experiment. They bring their laptops, open their AI tools, and work through ideas, questions, and real projects in real time.

We’re looking for facilitators who can make that experience engaging, approachable, and fun. People bring excitement, skepticism, practical questions, big questions, and plenty of uncertainty to these labs. The right facilitator can hold all of that with confidence, curiosity, and good humour.

This is a freelance, delivery-based role. Work will be ad hoc to start, likely a few sessions per month, with the potential for more as demand grows. Travel for in-person delivery will be paid separately.

What You’ll Do

  • Facilitate interactive AI Learning Labs for client groups

  • Deliver a strong, well-paced learning experience

  • Support participants as they work directly in AI tools during the session

  • Respond to live questions with confidence, clarity, and good judgment

  • Adapt to different groups, contexts, and levels of AI familiarity

  • Participate in prep calls, light customization, debriefs, and follow-up notes as needed

What We’re Looking For

We’re looking for people who bring:

  • Experience facilitating in a wide range of environments

  • Confidence working with AI tools

  • Curiosity and active experimentation with AI

  • Comfort with ambiguity and live dialogue

  • A human-centred approach to AI

  • A sense of humour and an ability to make learning lively, engaging, and accessible

You do not need to be a programmer or technical expert. But you do need to be highly comfortable using AI tools and able to support others as they learn.

This role is a strong fit for someone who is already actively using AI in their own work, keeps exploring what’s possible, and can navigate skepticism or resistance in a thoughtful, non-defensive way. Some of the most important moments in these labs happen when participants are hesitant, unsure, or asking hard questions.

Our Approach

At Overlap, our relational AI work is grounded in a practical, human-centred view of AI. We’re interested in how AI can augment human work, not replace it. We care about helping people think well, work well, and build confidence using these tools in context.

Role Details

Type: Freelance / contractor

Location: Greater Toronto Area

Delivery formats: In-person and virtual

Compensation: $100 - $125 per hour, with travel paid separately for in-person delivery.

Compensation for a half-day session will typically include 2 hours of prep time, travel time (if required), 3 - 4 hours of facilitation, and 1 hour of post-session follow-up.

Selection Process

Our process will include an interview, a paid observation of a live lab, and a paid co-facilitation before independent delivery.

We’re building a bench of trusted facilitators and expect to move quickly.

How to Apply

Please send either your resume or your LinkedIn profile, along with a short note answering these two questions:

  1. How are you currently using AI in your own work?

  2. What’s the most interesting or exciting thing you’ve discovered about AI recently?

Please send applications to:
Lee Cookson
Director, Strategy and Delivery
lcookson@overlapassociates.com