Freelance/Sessional Learning Facilitator

Location: Canada


We are delighted to be adding more Overlappers to our truly wonderful team! We are seeking a Freelance/Sessional Learning Facilitators.

About Overlap’s Design Practice

Before we get started on this journey together, we need to clarify what Overlap does and what we mean by “design”. For many people, design has become synonymous with visual arts, fashion, interiors or architecture—you might very well be a graphic designer reading this! While design can be about those things, the act of designing is all about solving problems and creating solutions. 

Overlap’s design practice focuses on solving “big picture problems” like organizational and societal challenges. Things like trying to improve childhood wellbeing in Canada, mixing design methods with policy advocacy, strategic plans and frameworks that drive new ideas and behaviours. We work collaboratively with diverse stakeholders, ask lots of questions to make sure we are solving the right problem, and launch solutions that put people first.

About Overlap’s Creative Problem Solving School

Overlap has been teaching customers and clients to use the methods in our design practice to bring transformative change to their organizations for 10 years. In 2021 we launched our Creative Problem Solving School, a home for all of our training and capacity building programs. The School runs a regular schedule of programming open to the public, in addition to courses and programs for Overlap corporate clients.

Diversity, Equity and Accessibility

Overlap welcomes you as you are. We place a high value on diversity and building an intentional, inclusive culture that welcomes employees to engage their whole selves. We know that diverse teams make our work better, our ideas more creative, and our process more rigorous. We are excited about candidates that bring new perspectives, new experiences and new strengths to our team. We strongly encourage people from all backgrounds and identities to apply. We believe in an equitable and inclusive recruitment process. If an accommodation would support your application, please reach out—we want to hear from you.

Job Description

Salary Band
Hourly Wage/Course

Reports to:
Design Director


Service Delivery, Creative Problem Solving School

Direct Reports

Virtual (with possibility to deliver live in-person, TBD)

Role Overview

This position is great for freelancers, gig workers or practitioners looking to set their own hours or add an additional service offering to their mix. We typically offer at least one training every week, enabling you to decide your workload. 

The Learning Facilitator reviews learning needs and uses suitable approaches to meet desired learning outcomes and learner needs. They learn and deliver learning content, support group discussions and respond to queries. They drive learner development by actively providing feedback and learner support. They review curriculum and recommend improvement areas, by collecting learner feedback and studying learning delivery approaches. They work with digital systems regularly.

They are well-spoken and skilled in managing multiple clients working across multiple different environments. They are able to build trusted relationships and create an engaging learning environment.

Key Job Responsibilities

Service Delivery 

  • Assess issues with learning environment to inform learning delivery approaches;
  • Attend to learner enquiries related to learning programs;
  • Collect data to assess impact of curriculum and services on learner’s performance;
  • Collect data and feedback to review learning needs;
  • Deliver lesson content to learners based on lesson plans;
  • Engage clients to understand desired group learning outcomes;
  • Prepare lesson plans based on client requirements and learner needs;
  • Review assessment data to identify learning gaps;
  • Review learning delivery methods and materials;
  • Review materials to ensure alignment with learner needs;
  • Review client needs and priorities;
  • Support group discussions for learners;
  • Support learning across multiple delivery modes based on lesson plans.

Leadership at Overlap 

  • Ability to expertly facilitate workshops, set design sprints and hold seminars and training sessions;
  • Ability to understand body language, or zoomy language, to support participation;
  • Strong interpersonal and client management skills;
  • Ability to communicate effectively with different audiences, including a solid competency in storytelling and public speaking. You are comfortable explaining your ideas to client stakeholders and to ideate the best means to present your facilitation work;
  • Overlap freelance and sessional positions are designed to meet the emerging needs and desires of a new world of work. We’re actively interested in individuals that might not want a full-time position with the company, but would like a place and team to be part of. In these roles, we expect individuals to operate as a representative of Overlap. This includes acting in a professional manner, using and championing Overlap’s proven methods, our brand and promise.


  • Be passionately curious—you are excited to be in the field and are as inquisitive about other people and their stories as they are empathetic;
  • Be captivatingly articulate in your storytelling—your presentations inspire the design team, get people out of their seats and bring tears to their eyes;
  • Support a client-centric perspective balancing Overlap needs, integrity of the design principles, values, and process;
  • A love of collaboration and learning, a fearless and positive attitude.


  • Minimum of 5+ years experience designing in complex projects or teaching design thinking and methods.
  • Education or direct experience in service design, business design or a related design discipline an asset.
  • Strong knowledge of human-centred design frameworks and associated methodologies.
  • Strong skills in live and virtual facilitation/teaching.
  • Ability to support different learning styles and outcomes for students.

Application Instructions

Please email your application as an attachment using the button below, or send it directly to careers@overlapassociates.com.

If you have any questions or need assistance with your application, please contact Ryan Voisin.

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