Master the fundamentals of working effectively with AI
Move beyond surface-level AI adoption in four guided weeks with a curated curriculum, hands-on practice, and a supportive community of AI-curious leaders just like you.
Our Alumni Work at:
Stop Paying the AI Confusion Tax
Every day, leaders who don't use AI effectively are paying for it in time, stress, and missed opportunities they often don't even notice.
When you use tools like ChatGPT, does it feel like you're barely tapping into their full potential for your daily work?
With so much noise from LinkedIn influencers and marketing claims, do you find it hard to sort real AI capabilities from the hype?
Have you ever paused to calculate how many hours you lose weekly to repetitive tasks that AI could streamline for you?
For most organizations, the AI implementation gap isn't technical.
It's not knowing what's possible.
of Fortune 500 companies are already using AI to improve their operations
hours saved weekly by professionals who use AI systematically
weeks is all it takes to transform you from overwhelmed to confident with AI
Learn How To Work Strategically With AI
Choose the right tools for the job, design simple, reusable workflows, and keep human judgment in the loop.
Shift From Busy To Strategic
Stop drowning in administrative work. Build AI systems that streamline repetitive tasks, giving you back 8-10 hours weekly for the high-impact decisions that matter.
Amplify Your Expertise With AI
Produce deeper insights, stronger proposals, and clearer strategies by learning to collaborate with AI as a thought partner who enhances your unique perspective.
Navigate The AI Landscape With Confidence
Build the confidence to match tools to tasks, turning the overwhelming AI landscape into a curated toolkit that actually serves your specific needs.
Transform AI Into Your Strategic Council
Move beyond generic chatbots and build a personalized team of AI advisors who understand your context, challenge your thinking, and accelerate your decision-making.
When the conversation changes from "Can AI do this?" to "Where else could it help?" you're on the right track.
Built for Busy Leaders Who Need Clarity
No coding, no tech speak, just structured guidance to reduce stress and improve the quality of your work.
Founders & Business Owners
Do more with the team you have.
Learn to streamline research, analysis, and routine tasks with AI, freeing you to focus on growth and innovation.
Consultants & Coaches
Deliver deeper insights faster.
Turn AI into a reliable assistant for discovery, analysis, and deliverables so you can spend more time with your clients.
Nonprofit Leaders
Balance admin and impact work.
Build AI systems for grant writing, donor communications, and reporting that give you hours back for program delivery.
Your AI Fluency Journey with Upskailed
Each week follows a simple, powerful rhythm: you'll learn a practical framework in our Tuesday workshop, refine it with expert guidance in the Friday mastermind, and immediately apply it to your work for a tangible result.
| Week | Tuesday Workshop | Friday Mastermind | Weekly Implementation |
|---|---|---|---|
| 1 | AI Fundamentals & Prompting | Prompting Lab & Workflow Setup | Revisit an Everyday Task with AI |
| 2 | Building Your AI Assistants | Persona & Project Clinic | Design Your Core Assistants |
| 3 | AI for Research & Strategy | Live Research Synthesis | Solve a Research Challenge |
| 4 | AI Implementation & Automation | Implementation Roadmap Session | Build Your 30-Day AI Plan |
From Overwhelm to First Wins
You’ll explore AI's current capabilities and recent breakthroughs that apply to your work, learning simple prompts that turn vague responses into clear, useful outputs right away.
From Repetitive Tasks to Reliable Systems
You’ll build your own small team of AI assistants that understand your work, creating repeatable workflows that begin to lift the weight of administrative tasks and free you for what matters.
From Information Overload to Strategic Clarity
You’ll learn to use AI as a research partner that transforms hours of searching into minutes of insight, allowing you to move forward on key decisions with confidence.
From Experimentation to Lasting Capability
You’ll solidify everything you've learned by designing a personal implementation plan, ensuring your new skills become a permanent, reliable part of your professional toolkit.
The Complete Upskailed System
We designed this system to turn AI overwhelm into practical skills, with supportive guidance at every step of your journey.
Your Guided Learning Path
Live weekly workshops to get your questions answered in real-time, so you can build momentum with confidence.
Hands-on mastermind sessions to help you apply new frameworks directly to your own work and challenges.
Your Tangible Takeaways
A personalized 30-day roadmap that gives you a clear, actionable plan for what to do after the course ends.
Your personal resource library of proven prompts and templates, becoming your go-to toolkit for daily tasks.
Your Ongoing Community & Support
Lifetime alumni community access for ongoing peer support and curated updates that cut through the noise.
Monthly office hours for continued guidance on new tools and any questions that come up along your journey.
My Commitment to Your Confidence
A full money-back guarantee because your peace of mind is paramount. If you participate fully and don't feel more capable and clear-headed about using AI, I'll refund your investment.
Meet Your AI Guide
I've spent thousands of hours in the AI trenches, testing what works and what doesn't. Now, I bridge the gap between cutting-edge possibilities and the practical reality of your daily work.
Teacher turned technologist.
I spent years making complex concepts click for students, and I bring that same patient, clear approach to AI education.
Builder of practical solutions.
I taught myself to code to solve real problems for educators, giving me deep empathy for non-technical professionals navigating new tools.
Ally to mission-driven organizations.
I help schools, nonprofits, and startups implement AI thoughtfully, focusing on real impact over flashy features.
Committed to your success.
If you don't see tangible value—through time saved or impact created—within 30 days of completing the course, I'll refund your investment entirely.
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I want to make sure AI actually works for you.
Show me you've participated and tried to implement what you've learned. If AI hasn't made your professional life notably better, you deserve your money back.
Leaders Like You, After Four Weeks
The most meaningful measure of our program's success is the real-world impact it has on the leaders who complete it. Their stories show the relief of finally having a clear path forward, without the hype or complexity.
"Before this course, I was stumbling my way through AI tools, picking models at random and hoping for the best. Now, I actually understand what each model does and when to use it."
— Kathryn Ashby
Executive Director, Marketing & Communications
Scouts Canada
"Jonathon is my trusted source for cutting-edge AI tools. He helps me achieve an outsized impact in my work with less time, money, and effort."
— Tanika McLeod
Co-Founder
OneCliq (acquired)
"Not only will he show you how to maximize AI tools, but he will also do so in a way that is encouraging and motivational."
— Angela Scarlett
Principal Lawyer, Ethical AI Law & Compliance
Multinationals Inc.
"Jonathon is an incredibly dedicated and committed instructor. His materials are thoroughly prepared and he brings the rare qualities of quiet passion and patience to his sessions."
— Paula Wickberg
Executive Leadership Coach & Communication Strategist
Paula Wickberg Consulting
"What are you doing? Get off your couch and do it right now. Carve some time out of your day to join Upskailed by Jonathon and learn about the future."
— Olu Villasa
Manager
Black Entrepreneurship Alliance
"This course delivered immediate, tangible results for me. I implemented weekly learnings right away and saw ROI from the first session. By week four I was humming along, refining and improving what I’d built."
— Kay Boamah
Co-Founder
Swiirl
Your Investment
This program is a strategic investment in your capabilities. Most participants reclaim enough time within the first month to more than cover the cost, but the real return is the lasting ability to collaborate effectively with AI.
$899.00
Discounted for teams of 3 or more.
I'll support you at every step with:
Four weeks of live, guided workshops to build your skills.
Hands-on mastermind sessions to apply them directly to your work.
A clear 30-day roadmap so you know exactly what to do next.
A personal library of templates and prompts to use right away.
Ongoing community and guidance so you're never stuck.
A full money-back guarantee because your peace of mind is paramount.
And my guarantee that you'll feel more confident and capable working with AI.
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The Questions I Hear Most
These are the questions and concerns I hear most often. I hope these answers help you decide whether this program is the right fit for your goals.
"I've tried ChatGPT a few times. Will this actually teach me something new?"
Using ChatGPT is like using 5% of Excel's features, and this course goes far beyond just using ChatGPT. You'll discover AI capabilities you didn't know existed like streamlining your entire board meeting prep, or researching clients in 10 minutes instead of 2 hours.
"How much time will this require?"
The core commitment is 90 minutes per week for the live sessions. For maximum results, I recommend 2-3 additional hours weekly for practice and implementation, including the Friday mastermind session. All sessions are recorded if you need to miss one.
"I'm not technical. Will I be able to keep up?"
This course is specifically designed for business professionals without technical backgrounds. I focus on practical applications using no-code AI tools, not programming or complex algorithms.
"How quickly will I see results?"
Most participants implement their first AI workflow improvement within 7 days of starting the program, often saving 3-5 hours per week immediately. By the end of the program, you'll have a complete implementation plan with both quick wins and long-term strategies.
"Will this be relevant to my specific industry?"
The course includes industry-specific examples and application exercises. During Week 4, you'll develop a personalized AI action plan for your exact business context.
"What makes this different from free online resources?"
While free resources can provide information, they rarely offer personalized guidance, structured implementation frameworks, or ongoing support. This program provides a systematic approach tailored to your specific business challenges, with direct access to me (Jonathon) for troubleshooting and strategy refinement.
"Do I need to use paid AI tools?"
While we explore various AI platforms, you can complete the entire course with one key subscription of your choice, costing roughly $25/month. Many participants start with free tools and upgrade only after seeing specific value. You'll learn exactly when paid versions are worth the investment for your use cases.
"What if I have to miss a session? Are the recordings available afterwards?"
Yes, the recordings are posted in our private community within a few hours of each session. Each recording includes quick summaries of the key takeaways to help you stay on track.
"What if I'm not satisfied with the course ?"
If you participate fully and don't feel more capable and clear-headed about using AI to support your work, I'll refund your investment.