Who We Are:

Twenty One Toys is an award-winning social enterprise that uses toys to teach empathy, failure and other key 21st century skills. First featured on TEDx, their multi-award winning Empathy Toy® is being used in thousands of schools and offices in 50 countries. Proving that toys are the new textbooks, Twenty One Toys is well on its way to creating the world’s first global community of empathic and resilient leaders thanks in part to the upcoming release of The Failure Toy in 2021. With workshops and training programs for all ages — even TIME magazine has praised their toys as a future technology!

Workshop Facilitator Lead Role:

You will work closely with our Director of Training and Facilitation to support the delivery and growth of our workshop and training offerings. You will also work closely with the customer engagement team to support discovery calls, demonstrations, and workshop and training follow ups.

What you will do specifically:

  • Lead our Empathy Toy® and Failure Toy® workshops
    • These workshops typically last between 90-mins and 3-hours, with some custom workshops lasting a full day
    • Audiences range in size from 15 - 300
    • For larger audiences, you will work with and oversee a team of additional contract facilitators
    • These workshops are often delivered to corporate teams. You should be prepared to lead sessions for clients in a wide variety of sectors, including financial and legal services, healthcare, post-secondary education, and not-for-profit, among others
  • Lead our Empathy Toy® and Failure Toy® InPerson and Online Training sessions
    • We currently offer 1-Day training on the Empathy Toy® and are in the process of designing similar training for our new Failure Toy. This is a full-day in-person session that provides teams or individuals a deep dive into facilitation techniques for our toys
    • We also offer 2hr online training over video conference as an orientation to clients who recently purchased a toy and are looking for tips and ideas to maximize its impact
  • Build long-term client relationships that lead to recurring engagements
    • You will ensure that clients feel supported, heard and excited to be playing with us over the course of multiple interactions
    • Essential client interactions include running consultation calls prior to each workshop and post workshop and training follow-ups
  • Running discovery call and demonstrations for inbound inquiries, walking new leads through our sales pipeline, and keeping your accounts up to date
    • You will lead scoping calls and demonstrations for new clients
    • You will be responsible for tracking and reporting on client relationships and sales leads, keeping detailed notes in our CRM
    • You will create, send and follow-up on estimates and invoices
    • You will share updates and insights with our sales and product design team during weekly sales meetings

We’re Looking For:

  • Minimum 3 - 5 yrs experience in a career involving frequent (weekly or biweekly) professional speaking and facilitation in one or more of the following: Emotional Intelligence, Leadership, Team-building, Innovation, Diversity & Inclusion
  • Minimum 1 - 2 yrs experience in customer service, sales, or equivalent
  • You have built and managed long-term client relationships
  • You have a diverse range of experiences with a variety of different client types, as evidenced by a robust and diverse professional network
  • You are an interdisciplinary thinker, able to make meaningful connections to a variety of subject areas when you facilitate
  • You are a dynamic, quick-witted and engaging presenter
  • You use humour and play strategically to increase enjoyment and audience engagement – but you also know how to hold space for serious conversations
  • You are excited to learn new things, as evidenced by a wide variety of professional and personal interests
  • You are a quick learner who is keen to both receive and provide feedback
  • You share our passion for our core values (view PDF)
  • You must be able to travel (have a driver’s license, up to date passport, and no criminal record). Our workshops and training require travel around the GTA, across Canada and Internationally.

This role is a great fit for you if:

  • You are an exceptional facilitator with customer service and sales experience looking for a more permanent home at a company where you can meaningfully contribute to a mission that is greater than you
  • You thrive in a small, highly collaborative team in which every member wears many hats
  • You are a lifelong learner who approaches your craft with curiosity, passion and humility

Special preference will be given to applicants who:

  • Have experience using our toys in their work
  • Can facilitate in multiple languages (French and Spanish are particularly valuable to our current client pool)

Reasons to be excited:

  • We are the leaders in using toys to teach skills like empathy and failure and are making waves in small businesses, and Fortune 500 companies around the world.
  • Our Failure Toy is set to be released in 2021 (with an already successful Kickstarter Campaign). It’s going to be an exciting year as we launch a brand new toy to our community.
  • There will be lots of travel opportunities and our clients are wonderful
  • You will be in the front seat of a growing startup. We are just at the beginning of our toy revolution, and with a focused effort we can continue to break records!
  • We have a swing!


Please email hireme@twentyonetoys.com and include "Workshop Facilitator Lead!” in the subject line.

Send us:

  • The link to your Linkedin (or equivalent)
  • A link to your video cover letter!
    • To give us a sense of your presentation style and personality, record a 1-2 min. video of yourself explaining why you’d be a great addition to our team
    • Upload to youtube as unlisted and include the link in your email
    • Bonus points: send us your favorite GIF

We are an equal opportunity employer and strongly support applications from diverse backgrounds and communities. Only candidates under consideration will be contacted.

Thanks for your interest!

Application now closed.