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.

I lived the before-state. I was a high school math teacher whose evenings and weekends disappeared into reports and emails, the kind of work that keeps good teachers from the teaching. 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. Somewhere in those hours I found what 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 the method asks for your thinking instead of replacing it. The more of yourself you bring, the better the result, and the more it stays yours.

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. The solutions are available, just unevenly distributed. I'm here to distribute them.

The classroom years explain the method. As a high school math teacher in Toronto's French-language school system, Jonathon watched administrative work crowd out the 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.

The curiosity is still the engine. 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.