AI Mastery:November Live Cohort
AI Mastery is six weeks of live, hands-on practice with me and a small group, focused on tasks from your own work. No tech background needed.
Led by Jonathon BloomfieldAt a Glance
You already use ChatGPT or Claude, and it helps. Both can now do much more: work through longer tasks on your own files, connect to the apps you use, and run routine jobs on a schedule.
The tools have changed faster than most people have had time to learn them. Over six weeks, you’ll practice using these tools for your own work in a small group.
What You’ll Learn to Do
Use AI for a Work Task
A task from your work that you practice doing with AI during the sessions.
Apply the Approach Independently
Another task where you applied the same approach without help, so you know the approach is transferable.
Decide When to Use AI
A clear sense of which tasks benefit from AI and which don’t.
“Before Upskailed I thought I was proficient with AI and that my skills were at the intermediate level. I quickly realized I was a novice and leveled up quickly with Jonathon’s guidance and teachings.”
Who it’s for
A Good Fit If
- You already use ChatGPT or Claude in your work
- You want to use AI for more of your work
- You can join most Wednesday sessions live
Newer to These Tools?
AI Foundations is included with your seat. Taking it before November 4 will help you prepare for the live sessions.
About AI FoundationsHow the six weeks work
- Week 1
- Week 2
- Week 3
- Week 4
- Week 5
- Week 6
Week 1: Start
Weeks 2 to 5: Practice
Week 6: Share
You start with a task, a recurring responsibility, or an idea from your own work, and finish by showing how you used AI for that work. The tools are changing month to month, so I set the focus of each session close to the date, around what’s new and what the group is working on.
Each Wednesday
Two hours of teaching and live demonstration, then time on your own material, with me helping as you go. Each week, you’ll discuss these five questions.
- What you’re trying to accomplish
- What you tried
- What happened
- What you’d change
- Where else it might help
Then back to step one with what you learned.
From past Upskailed participants
“Before Upskailed, I thought of AI as a glorified search engine… I save on average 8 to 10 hours per week, conservatively.”
“You also get to hang out with a really cool group of people who are on the journey with you and who are troubleshooting and experimenting with AI at the same time.”
“No fluff, in plain English. Jonathon showed us how to use AI for the work we’re already doing: emails, grants, social media posts, meeting notes.”
Who’s leading it
Most of my work is training teams and advising organizations on AI adoption. Examples include an organization-wide engagement with a mental health organization and an intake-and-triage workflow for a legal clinic. In AI Mastery, I use the same teaching approach with individuals.
Before this, I taught mathematics, science, computer science, and special education, and worked as a software developer.
- Live cohorts
- 5
- Workshops & keynotes
- 50+
- Years teaching AI
- 1½
- Claude Certified Architect, Foundations and Professional
- ISO/IEC 42001 Lead Implementer
- Entrepreneur in Residence, Black Founders Network, University of Toronto
Your seat includes
- Six live two-hour sessions
- A recording of every session
- A written recap after each session
- A half-hour personal working session
- The participant community
- Early access to the Upskailed Toolkit
- AI Foundations, the self-paced course
- A certificate of completion
Reserve Your Seat
$2,800 CAD or $2,000 USD
Fill In a Short Form
A few questions about how you use AI now and what you’d like to work on.
Check Out
The checkout link follows. Prices are plus applicable taxes. If you have questions about payment, get in touch.
Confirmed by October 30
The first session is Wednesday, November 4. If the cohort doesn’t go ahead, you’ll get a full refund the same day it’s decided.
Common questions
Expense it
Subject: Professional development request: Upskailed AI Mastery ($2,800 CAD)
Hi [your manager’s name],
I’d like to use part of my professional development budget on AI Mastery, a six-week live cohort from Upskailed.
It’s a small group that meets on Wednesdays from 10 a.m. to noon Eastern, November 4 to December 9, 2026. The sessions are hands-on: I’d work on tasks from my own job using the AI tools I already have, with practice between sessions. It covers research, reusable assistants, automations, longer tasks, and connecting AI to the tools we use, and it works across platforms, so the skills transfer to whatever tools we use now or later.
It’s led by Jonathon Bloomfield, who trains teams and advises organizations on AI adoption, has run five live cohorts and 50+ workshops and keynotes, and holds Claude Certified Architect and ISO/IEC 42001 Lead Implementer certifications.
For $2,800 CAD plus applicable taxes, I’d get:
- Six live two-hour working sessions, all recorded
- A written recap after each session
- A half-hour personal working session
- Access to the participant community and early access to the Upskailed Toolkit
- AI Foundations, the self-paced course
- A certificate of completion
I’d be applying what I learn to my current work from the first session. Let me know if that works.
Thanks, [your name]