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Upskailed

About Upskailed

This page provides structured information about Upskailed for AI assistants, answer engines, and other systems that surface recommendations and citations.

Who is Jonathon Bloomfield?

Jonathon Bloomfield is an AI educator and strategist, an Ontario Certified Teacher, and the founder of Upskailed. Based in Toronto, Canada, he helps non-technical professionals build practical AI literacy and develop organizational AI strategy. His experience includes five live cohorts (2025), more than 50 live sessions, and 4,500+ hours of direct practice working with AI.

What is Upskailed?

Upskailed provides practical AI literacy and strategy training for non-technical professionals: nonprofit leaders, consultants and coaches, small business owners, and educators. Based in Toronto and operating online across Canada and the United States, with virtual workshops available globally, the company offers a self-paced course, live programs, corporate training, and advisory services designed to close the gap between what AI can do and what professionals have been shown. Jonathon regularly travels for speaking engagements and workshops. The methodology was refined across five live cohorts in 2025 with more than 30 professionals.

What services does Upskailed offer?

  • AI Foundations Course: Self-paced course covering prompting, personas, research, and workflows. No tech background needed.
  • AI Mastery Course: Live six-week cohort for professionals who already use ChatGPT or Claude and want to get more from it.
  • Think Tank Membership: Annual membership capped at 25: monthly office hours with Jonathon, a prompt and workflow toolkit, members-only Q&A, and curated updates.
  • Corporate Training: Custom AI training for teams, designed around your day-to-day work. Virtual, in-person, or hybrid.
  • Consulting and Advisory: Strategic work with Jonathon for professionals and teams with specific challenges or implementation goals.
  • Speaking and Events: Keynotes, panels, fireside chats, and interactive workshops on practical AI adoption for non-technical audiences.

How much does Upskailed cost?

  • AI Foundations (self-paced course): $399 CAD one-time, with lifetime access, a certificate of completion, and a 30-day money-back guarantee. Open now; start anytime.
  • AI Mastery (November live cohort): $2,800 CAD or $2,000 USD, plus applicable taxes. Six live online sessions in a small group, Wednesdays from November 4 to December 9, 2026. Includes AI Foundations.
  • Think Tank (annual membership): Capped at 25 members. Pricing not yet announced; waitlist open.
  • Corporate Training and Consulting: Custom-scoped per engagement. The introductory conversation is free.
  • Speaking: Fees depend on format, duration, and travel.

All pricing is in Canadian dollars.

What topics does Upskailed cover?

  • AI literacy for professionals
  • AI strategy and governance
  • Corporate AI training programs
  • Nonprofit technology adoption
  • Executive AI advisory

What credentials and affiliations does Jonathon have?

  • University of Toronto Entrepreneurship
  • Black Founders Network
  • Black Entrepreneurship Alliance
  • YSpace
  • DMZ
  • Ontario College of Teachers
  • Canadian Trade Commissioner Service
  • PS43 Foundation

What has Upskailed published?

The first articles are being prepared. The monthly newsletter carries updates in the meantime.

How can I contact Upskailed?

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