Jonathon Bloomfield

Nobody taught us how to work with AI. It arrived inside the tools we already use, with no manual, and everyone has been figuring it out alone: typing a question into a chat window between meetings and hoping for the best. That has nothing to do with ability. You don't know what you don't know.

Before learning to use AI, I struggled with the same problems. I was a high school math teacher who spent evenings and weekends writing reports and emails, administrative work that leaves teachers less time to prepare and teach. The frustration made me curious. I taught myself to code, built my own tools, and have since put more than 4,500 hours of direct practice into learning how to work with AI. Through that practice, I developed the approach I now teach: the difference between using AI and collaborating with it, and how much of that difference is learnable.

Upskailed is where I teach it. I work with people who run things without a technical background or a team behind them: nonprofit leaders, consultants and coaches, small business owners, and educators. We work in plain language, on your own work, and you use your own judgment to direct and evaluate the AI’s work. Providing your expertise, preferences, and context helps AI produce work that reflects your intentions.

Across five live cohorts and more than fifty sessions, I've watched capable people arrive overwhelmed by the pace and leave confident in their own judgment. Many professionals haven’t been shown these methods. I teach them.

His teaching experience shaped his approach to AI training. As a high school math teacher in Toronto's French-language school system, Jonathon watched administrative work reduce the time available for teaching. He taught himself to code, built the productivity tools he wished he'd had, and turned that work into Edventive, his EdTech company, and eventually into Upskailed. He is an Ontario Certified Teacher, an Entrepreneur in Residence with the University of Toronto's Black Founders Network, and speaks regularly at industry events on practical AI adoption. His clients now cover in weeks what took him years to learn and apply.

Curiosity continues to motivate his work. In his words: "I feel like we're living through history. I'm lucky that I get to explore my curiosities in ways that can be helpful to others."

5 live cohorts (2025) · 50+ live sessions · 4,500+ hours of direct practice

The methodology was refined across five live cohorts in 2025 with more than 30 professionals from nonprofit, consulting, education, and small business sectors, then became the self-paced course and programs Upskailed offers today.