Question 1

Is this for me if I’m not technical?

Accepted Answer

Yes. Everything Upskailed offers is designed for people who aren’t technical. You don’t need to know how to code, and you won’t learn to code. You’ll learn how to work with AI tools practically: prompting, research, content creation, workflow design. If you can use email and a web browser, you have the technical skills you need.

Question 2

How do I know which offering is right for me?

Accepted Answer

It depends on where you are and what you need. AI Foundations is a good starting point if you’re new to AI or want to build a solid base. AI Mastery goes deeper and is designed for people who’ve completed Foundations or have equivalent experience. The Think Tank is ongoing advisory and peer support for professionals who want to keep sharpening their practice after Foundations and Mastery. Corporate Training is for teams and organizations. Consulting and Advisory is strategic work with Jonathon for professionals and teams with specific challenges. If you’re not sure, reach out and Jonathon will help you figure it out.

Question 3

What if I’ve already been using AI on my own?

Accepted Answer

That’s common, and it’s a great starting point. Many of the professionals who get the most out of the training arrive already using ChatGPT or similar tools but sense there’s more they’re not seeing. The program builds on what you already know and helps you discover capabilities you hadn’t considered. If you’re already experienced, AI Mastery or Consulting might be a better fit than Foundations.

Question 4

What AI tools do I need?

Accepted Answer

You’ll need access to at least one AI platform. The training covers multiple platforms including ChatGPT, Claude, and Gemini so you can learn to choose the right tool for each task. A paid subscription to one of these, around $20 to $30 a month, gives you the best experience, but you can start with free versions. There’s no required software beyond that.

Question 5

Will what I learn become outdated as AI changes?

Accepted Answer

The specific tools will keep evolving, but the skills you learn transfer across platforms and updates. Upskailed teaches you how to think about AI, how to prompt effectively, how to evaluate output quality, and how to build workflows. Those skills apply whether you’re using today’s models or whatever comes next.

Question 6

Do you teach people how to use AI for specific tasks?

Accepted Answer

Yes. The training covers practical applications like research and analysis, content creation, workflow design, and working with AI on tasks you already do. Participants in past cohorts have used what they learned for grant writing, client proposals, market research, meeting preparation, email drafting, onboarding guides, and more. Everything you build uses your own work, so it’s immediately useful.

Question 7

How much time does this take?

Accepted Answer

AI Foundations is a self-paced course with about two and a half hours of content plus exercises. You work through it on your own schedule with lifetime access. AI Mastery is a 6-week live program with two-hour weekly sessions. Corporate Training is scheduled around your team’s availability. Consulting is flexible.

Question 8

Who teaches the program?

Accepted Answer

Jonathon Bloomfield, Upskailed’s founder. Jonathon has led five cohorts of AI training with over 30 professionals across nonprofit, consulting, education, and small business sectors. He leads every program, workshop, and consulting engagement personally.

Question 9

What’s the difference between the programs and the services?

Accepted Answer

The programs (AI Foundations, AI Mastery, and the Think Tank) are for individuals building and maintaining their AI skills. You follow a curriculum, join an ongoing membership, or both. The services (Corporate Training and Consulting and Advisory) are custom work with Jonathon on your organization’s specific challenges. Think of programs as investing in your own growth and services as bringing Upskailed into your team.

Question 10

What is the Upskailed Think Tank?

Accepted Answer

The Think Tank is a small, ongoing membership for professionals who want continued advisory, tools, and peer support as they work with AI. It includes monthly live office hours with Jonathon, a prompt and workflow toolkit, a members-only Q&A space, and a curated reading and watching list. Membership is capped to keep the group personal.

Question 11

Who is the Think Tank for?

Accepted Answer

Professionals who have completed AI Foundations (or equivalent training) and want ongoing support as they apply what they’ve learned. If you’re past the basics and want to keep sharpening how you work with AI, the Think Tank is designed for you.

Question 12

How is the Think Tank different from Foundations and Mastery?

Accepted Answer

AI Foundations and AI Mastery teach the skills. The Think Tank is where you continue practicing them with ongoing guidance, stay current as tools evolve, and get help with the specific challenges that come up in your work.

Question 13

What makes Upskailed different from other AI training?

Accepted Answer

The training is built from the ground up for non-technical professionals. It teaches transferable skills (prompting, evaluation, workflow design) that work across platforms and updates, so you’re not dependent on any single tool. Everything is grounded in outcomes from five cohorts of working professionals, corporate training sessions, and Jonathon’s personal explorations.

Question 14

Will this help?

Accepted Answer

It takes effort. AI training isn’t instant, and the results depend on how much you put in. That said, participants across five cohorts have consistently reported saving hours per week on tasks they used to do manually, discovering applications for AI they hadn’t considered, and approaching their work with noticeably more confidence and clarity. Upskailed offers a 30-day money-back guarantee on AI Foundations.

Question 15

I work in the nonprofit sector. Is this relevant to me?

Accepted Answer

A significant portion of Upskailed’s participants come from nonprofits and social impact organizations. The training has been used for grant writing, board documentation, stakeholder communications, program reporting, and donor research. The skills are the same regardless of sector.

Question 16

How much does it cost?

Accepted Answer

AI Foundations is $399 CAD, one-time, with lifetime access and a 30-day money-back guarantee. The Upskailed Think Tank and AI Mastery pricing is being finalized (you can join the waitlist to be notified). Corporate Training and Consulting and Advisory are custom-priced based on scope. All pricing is in Canadian dollars.

Question 17

Is my data safe when using AI tools?

Accepted Answer

Yes. The training covers how to configure privacy settings on AI platforms, what information to avoid sharing with AI tools, and how to use AI safely with sensitive content. Upskailed does not share, sell, or use your personal information beyond what’s needed to deliver the training. For detailed privacy practices, see our privacy policy.

Question 18

What if I have a question that’s not answered here?

Accepted Answer

Get in touch. Jonathon typically responds within 2–3 business days. There’s no obligation and no sales pitch.

Frequently Asked Questions

Frequently Asked Questions

Getting started

Tools and skills

About the training

About the Think Tank

About Upskailed

Practical details

Still have questions?

Frequently Asked Questions

Frequently Asked Questions

Getting started

Is this for me if I’m not technical?+

How do I know which offering is right for me?+

What if I’ve already been using AI on my own?+

Tools and skills

What AI tools do I need?+

Will what I learn become outdated as AI changes?+

Do you teach people how to use AI for specific tasks?+

About the training

How much time does this take?+

Who teaches the program?+

What’s the difference between the programs and the services?+

About the Think Tank

What is the Upskailed Think Tank?+

Who is the Think Tank for?+

How is the Think Tank different from Foundations and Mastery?+

About Upskailed

What makes Upskailed different from other AI training?+

Will this help?+

I work in the nonprofit sector. Is this relevant to me?+

Practical details

How much does it cost?+

Is my data safe when using AI tools?+

What if I have a question that’s not answered here?+

Still have questions?