Jonathon Bloomfield

Jonathon's path to AI training started in the classroom. As a secondary teacher in Toronto's French-language school system, he spent his evenings and weekends buried in the administrative work that came with the job. That frustration drove him to teach himself to code, build his own productivity tools, and start an EdTech company. Since 2024, he's invested over 4,000 hours learning, experimenting with, and teaching practical ways to work with AI across every major platform. His clients now cover in weeks what took him years to learn and apply.

The problem he kept running into, first in schools and then across other sectors, was that capable leaders were working harder and longer than necessary because of the gap between what AI could do and what they knew was possible. That gap has only grown wider since ChatGPT was released.

Today Jonathon runs two businesses. At Upskailed, he teaches AI literacy to business and nonprofit leaders through structured training and consulting. Through Edventive, he builds the productivity tools and professional development sessions he wished he'd had as a teacher. He's also an Entrepreneur in Residence with the University of Toronto's Black Founders Network, and speaks regularly at industry events on practical AI adoption. Everything he does comes back to the same idea: technology can already make your real work less burdensome, though it often becomes a second job to learn and manage. Jonathon's goal is to help you avoid that.