# Upskailed — Full Content for LLMs > Practical AI training, consulting, and implementation support for business and nonprofit leaders. Learn to work with AI through programs, advisory, and hands-on guidance. This document contains the complete content of all indexed pages (including blog, privacy, and case studies pages), articles, and case studies on https://upskailed.com. It is designed for AI systems that need comprehensive context about Upskailed. For a shorter summary, see /llms.txt. ## About Upskailed provides AI literacy and strategy training for non-technical business and nonprofit leaders. Founded by Jonathon Bloomfield. ### Services - AI Foundations Course: Asynchronous course covering prompting, personas, research, and workflows. No tech background needed. - AI Mastery Course: Live 6-week program for leaders who've built their AI fundamentals and want to go further. - Corporate Training: Custom AI training for teams, designed around your day-to-day work. Virtual, in-person, or hybrid. - Consulting and Advisory: Strategic work with Jonathon for leaders and teams with specific challenges or implementation goals. - Speaking and Events: Keynotes, panels, fireside chats, and interactive workshops on practical AI adoption for non-technical audiences. # Full Page Contents --- ## Page: Upskailed | AI Training, Consulting & Advisory for Leaders URL: https://upskailed.com/ # AI upskilling that starts where you are. If AI still feels like something you should have figured out by now, you're not behind. Through training, advisory, and ongoing support, we're here to guide you from first steps to long-term strategy. ## Programs 1. **AI Foundations** — Self-paced course covering prompting, research, workflow design, and cross-platform AI fluency. No tech background needed. [Learn more](/programs/foundations) 2. **AI Mastery** — Live 6-week program for leaders ready to build advanced research workflows, AI teams, and organizational strategy. [Learn more](/programs/mastery) 3. **Think Tank** — Ongoing advisory, tools, and peer support for professionals working with AI. Includes monthly office hours, a toolkit, and curated updates. [Learn more](/programs/think-tank) ## Services 1. **Corporate Training** — Hands-on workshops designed around your team's day-to-day work, tools, and goals. Virtual, in-person, or hybrid. [Learn more](/services/corporate-training) 2. **Consulting and Advisory** — Ongoing guidance for leaders who need help figuring out how AI can support their work and organization. [Learn more](/services/consulting) 3. **Speaking** — Keynotes, panels, and workshops on AI adoption, strategy, and implementation for conferences and events. [Learn more](/services/speaking) ## Who We Serve ### Learn at your own pace AI training designed for your schedule and your day-to-day work, whether you're just getting started or ready for more. - AI Foundations: self-paced AI fluency course - AI Mastery: 6-week live program (waitlist open) - Plus frameworks and templates you'll keep using ### Training for your whole team For teams and organizations who would benefit from everyone working with AI, instead of a few people figuring it out alone. - Corporate Training: workshops built around your team's day-to-day work - Consulting and Advisory: ongoing strategic guidance and implementation - Every engagement includes a custom Team AI Playbook ## Next Steps Not sure which option fits? Start with a short conversation. We'll help you figure out what would actually be useful. - [Schedule a conversation](/contact) - [View programs](/programs) - [Explore services](/services) --- ## Page: About Jonathon Bloomfield URL: https://upskailed.com/about # Jonathon Bloomfield Teacher, AI obsessive, and founder. ## Background 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](/programs), he teaches AI literacy to business and nonprofit leaders through structured training and consulting. Through [Edventive](https://edventive.co), 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](/services/speaking) 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. ## What People Say > "Our Board is grateful for Jonathon's engaging delivery and his commitment to empowering sector leaders with knowledge to navigate and model positive AI use. We strongly recommend Jonathon Bloomfield to any organization seeking to improve its AI literacy and leadership capacity." — Cléo Charlebois, Executive Director, NEOFACS ## Next Steps Interested in working together? Start with a conversation, or explore the training options to find the right fit. - [See our programs](/programs) - [Get in touch](/contact) --- ## Page: AI Consulting, Training, and Speaking for Business Leaders URL: https://upskailed.com/services # Three ways to work with Jonathon on AI Custom team training, strategic consulting, and conference speaking for non-technical leaders and organizations. ## 01. Corporate Training Training designed around your team's day-to-day work. Half-day workshops, multi-session intensives, or ongoing programs. Virtual, in-person, or hybrid. Led by Jonathon. **What you get:** - Discovery call and custom program design - Live training sessions with your team - Team AI Playbook with workflows, prompts, and strategies - Follow-through support after training [Learn more](/services/corporate-training) ## 02. Consulting and Advisory Strategic work with Jonathon and your team for leaders who need more than a course. Focused sessions on your specific challenges, whether that's workflow design, organizational strategy, or ongoing implementation support. **What you get:** - Free introductory conversation to figure out what you need - Scoped proposal with clear deliverables and timeline - Working sessions tailored to your priorities - Ongoing advisory available on a retainer basis [Learn more](/services/consulting) ## 03. Speaking and Events Jonathon speaks at conferences, corporate events, and industry panels on practical AI adoption for non-technical audiences. Keynotes, fireside chats, and hands-on workshops, each tailored to your audience and event theme. **What you get:** - Keynotes and conference talks customized to your audience - Panel participation with a practical, grounded perspective - Interactive workshops where participants build real workflows - Talks designed for non-technical audiences at every comfort level [Learn more](/services/speaking) ## Not sure where to start? Start a conversation. We'll help you figure out which option makes sense for where you are right now. ## Common questions ### How do I know which service is right for me? It depends on what you need right now. If you want your team aligned on AI, Corporate Training is the place to start. If your organization needs help with a specific challenge, Consulting gives you dedicated time with Jonathon's support. If you're bringing Jonathon to an event, Speaking covers keynotes, panels, and workshops. In case you're not sure, please reach out and we'll help you figure it out. ### What if I'm not sure what I need yet? Start a conversation. Jonathon's initial conversations are free and exploratory. You don't need to know the exact service before reaching out. Describe your situation and he'll help you figure out the right approach. ### Can I combine services? Yes, and many clients do. A conference workshop often leads to Corporate Training for the broader team. Consulting clients sometimes start with a course to build foundational skills first. Jonathon will suggest what makes sense based on where you are, and won't upsell you into more than you need. ### How much do services cost? Corporate Training and Consulting are scoped per engagement, so pricing depends on the format, duration, and complexity involved. Speaking fees depend on the event format and travel requirements. Jonathon works with a range of budgets. Please share your situation in the inquiry form and he'll let you know what's possible. ### How long does a typical engagement take? It varies. Corporate Training can be a single half-day workshop or a multi-week program. Consulting engagements are typically a series of working sessions over several weeks, or scoped to a specific project that may take longer. Speaking engagements are usually a single event. During your initial conversation, Jonathon will recommend a realistic timeline based on your situation. ### Do I need to take a course before working with Jonathon? No. The courses (AI Foundations and AI Mastery) are designed for individual learners. The services on this page are for organizations, teams, and leaders who want direct engagement with Jonathon. That said, some consulting clients find it helpful to build foundational skills through a course first. Jonathon will let you know if a course would serve you better than consulting. ### Can you work with our team virtually? Yes. Each service works well via video conferencing, although many clients prefer to meet in person. Jonathon is based in Toronto, Canada, and is open to traveling for in-person meetings. ## Also available **Want to learn on your own schedule?** [AI Foundations](/programs/foundations) is an asynchronous course covering practical AI fundamentals for non-technical leaders. No tech background needed. **Ready to go deeper?** [AI Mastery](/programs/mastery) is a live 6-week program with small group sessions and personalized feedback from Jonathon. --- ## Page: AI Consulting for Leaders | Consulting and Advisory URL: https://upskailed.com/services/consulting # Consulting and Advisory Strategic work with Jonathon for leaders who need more than a course. Focused sessions on your specific challenges, from workflow design to organizational strategy to implementation coaching. ## How It Works ### Step 1. Introductory conversation A free, informal conversation to figure out what you need, to talk through your situation and to see if working together makes sense. ### Step 2. Scope and proposal If there's a fit, Jonathon puts together a clear proposal outlining what you'll work on, how many sessions, what it will cost, and what you'll walk away with. ### Step 3. Working sessions The real work happens here. Jonathon will work with your team to help you tackle your specific challenges. This could mean designing AI workflows for your team, suggesting software worth piloting, working through an organizational strategy, or something else entirely. The agenda is yours. ### Step 4. Deliverables and ongoing support You walk away with whatever we've built together: robust workflows, a strategic plan, refined proposals, or other deliverables specific to your engagement. For leaders who would like continued access, ongoing advisory is available on a retainer basis. ## What We Can Help With - **AI workflow design** — Build AI workflows to support your day-to-day work. Whether that's research, content creation, client communication, or internal operations, you'll leave with approaches you can put to use the same week. - **Organizational AI strategy** — Figure out how AI fits into your organization's work, now and over the next year. Jonathon will help you create a practical plan your team can execute, accounting for where they are today and how quickly the tools are changing. - **Grant writing and proposals** — Use AI to strengthen your grant applications and funding proposals. Jonathon will help you build solid processes for funder research, narrative development, and application drafting so the next round takes days instead of weeks. - **Implementation coaching** — For leaders who've started experimenting with AI but aren't seeing consistently positive results. Jonathon will work through your challenges and help you build more effective AI collaboration habits and workflows. - **Ongoing advisory** — Continued access to Jonathon on a retainer basis. Monthly or quarterly sessions, depending on what you need. Useful for leaders rolling out AI across their organization who want a sounding board as new challenges come up. ## Common Questions **Who is consulting for?** Leaders who need more than a course. If you have a specific challenge you want to work through with someone who understands both AI and the kind of work you do, consulting is the most direct way to get there. Past clients include nonprofit executive directors, independent consultants, small business owners, and startup founders. The common thread is that they had a specific situation they wanted help with. **How is this different from taking a course?** The courses ([AI Foundations](/programs/foundations) and [AI Mastery](/programs/mastery)) teach a structured curriculum to a group. Consulting is entirely shaped by your situation. There's no syllabus. You bring the challenges, and Jonathon works through them with you. Some clients take a course first and then use consulting to go deeper on specific applications. Others skip the course and start here because they already have a clear problem to solve. **What does the introductory conversation look like?** It's a free, informal call. You describe what you're working on and what you're trying to figure out, Jonathon asks questions to understand your situation, and by the end, you'll both have a sense of whether working together makes sense and what it would look like. **How many sessions does a typical engagement involve?** It varies. Some clients accomplish what they need in two or three focused sessions. Others work with Jonathon over several weeks or months as they implement changes across their organization. The scope is defined during the proposal stage so you know what to expect before you commit. **Can Jonathon help with grant writing?** Yes. Grant writing and proposal development is one of the most common consulting areas. Jonathon helps you build repeatable approaches for funder research, narrative development, and application drafting that save significant time without sacrificing quality. This is especially relevant for nonprofit leaders who spend large portions of their time on funding applications. **What is the ongoing advisory retainer?** For leaders who want continued access to Jonathon after an initial engagement, ongoing advisory provides regular sessions on a monthly or quarterly basis. The relationship evolves as your challenges do. Some clients use retainer sessions for strategic check-ins as they roll out AI across their organization. Others use them to work through new problems as they come up. The structure is flexible. **Do I need to be technical?** No. Consulting is designed for the same non-technical audience as everything Upskailed offers. You don't need to understand how AI models work. You need to understand your own work, and Jonathon handles the rest. If technical concepts come up, he explains them in plain language. **How much does consulting cost?** Pricing is scoped per engagement based on the number of sessions, the complexity of the work, and whether ongoing advisory is included. Jonathon will put together a clear proposal after the introductory conversation so you know exactly what it costs before you commit. He works with a range of budgets. **How quickly can I get started?** Availability is limited, but Jonathon can usually schedule an introductory conversation within a week or two. From there, the timeline depends on your situation and how quickly you want to move. If you have an urgent need, please mention it in the inquiry form and he'll do his best to accommodate. [Start a conversation](/contact) --- ## Page: AI Training for Teams and Organizations | Corporate Training URL: https://upskailed.com/services/corporate-training # Corporate Training AI training designed around your team's day-to-day work. Half-day workshops, multi-session intensives, or ongoing programs. Virtual, in-person, or hybrid. Led by Jonathon. ## Delivery Formats ### Half-Day Workshop A single morning or afternoon session introducing your team to what's possible with AI. We'll cover current AI capabilities, prompting fundamentals, industry-specific applications, and hands-on practice tailored to your team's needs. ### Multi-Session Intensive Multiple sessions over days or weeks, going deeper into workflow design, team AI adoption, and building shared practices. We'll build a Team AI Playbook that captures your workflows, prompts, and strategies so the learning continues seamlessly after the program ends. ### Ongoing Program An extension of the multi-session program, with recurring sessions over weeks or months, building your team's AI capability at a sustainable pace. The team will keep improving workflows, while staying informed on the latest AI capabilities, tools, and best practices. ## What your team gets - **Discovery call and custom design** — We'll set up a conversation to understand your team goals, challenges, tools and experience levels. Then, we'll suggest where AI might help and design a training program tailored to your group. - **Training built around your work** — The sessions will draw from your team's actual documents, workflows, and challenges as training material. Your team will work with real examples from their work, not generic case studies. - **Live sessions with Jonathon** — Jonathon leads every session personally, with the goal of getting your team comfortable and effective with AI tools they can use immediately. - **Follow-through after training** — Post-training support helps keep your team applying what they've learned. Includes access to Jonathon for questions as workflows become part of everyday work. - **Team AI Playbook** — We'll co-create a custom Team AI Playbook that captures the workflows, prompts, and strategies we build during the program, so the team can continue improving and scale use over time. ## Let's talk about your team Tell us a bit about your organization and what you're looking for. We'll follow up within a few business days. ## Common questions ### How many people can participate in a training session? There's no fixed minimum or maximum. Jonathon has worked with leadership teams of four and departments of fifty. The format adapts to fit: smaller groups allow more hands-on practice and individual attention, while larger groups work well for keynote-style introductions followed by breakout exercises. If your group is very large, a workshop-plus-breakout structure usually works best. Please describe your team in the inquiry form and Jonathon will recommend an approach. ### Does my team need any AI experience before the training? No. The training is designed for non-technical professionals. Jonathon meets your team wherever they are, whether that's "I've never opened ChatGPT" or "I've been experimenting but I'm not getting consistent results." The discovery call covers your team's current experience level so the sessions can be calibrated appropriately. ### What's the difference between a half-day workshop and a multi-session program? A half-day workshop covers prompting fundamentals, cross-platform fluency, and hands-on practice using your team's own examples. It's a strong starting point for teams that want practical exposure in a single session. A multi-session program goes deeper into workflow design, team AI adoption, and building shared practices over days or weeks. The multi-session format also includes the co-creation of a Team AI Playbook. ### What is the Team AI Playbook? A custom document your team keeps after training. It captures workflows, prompts, and strategies built during the program, specific to your team's work. It's included in multi-session programs and serves as a reference your team can continue using and building on after the training ends. ### Can training be delivered virtually? Yes. Two-hour sessions and half-day workshops work well over video conferencing. Multi-session programs can be fully virtual, fully in-person, or hybrid. For sessions that involve participants working with AI tools in real time, Jonathon will share specific technical setup requirements once the format is confirmed. ### How does the discovery call work? It's a free conversation where Jonathon learns about your team, what you do, and where AI might help. He'll ask about your team's roles, the kind of work they do day to day, and what you're hoping the training will accomplish. From there, he designs a program specifically for your group. No commitment required. ### How much does Corporate Training cost? Pricing depends on the format, number of sessions, group size, and whether the training is virtual or in-person. Jonathon works with a range of budgets, from funded corporate programs to nonprofit organizations with limited training resources. Share your situation in the inquiry form and he'll put together a proposal with clear pricing. ### Does Jonathon lead the training personally? Yes. Every session is led by Jonathon. The person you speak with during the discovery call is the person who designs and delivers your training. ### What happens after the training ends? Follow-through support is included. Your team has access to Jonathon for questions as they put new workflows into practice. For teams that want sustained support beyond the initial engagement, ongoing advisory is available through [Consulting and Advisory](/services/consulting). ## Also available **Looking for individual training?** [AI Foundations](/programs/foundations) is an asynchronous course you can complete on your own schedule, and [AI Mastery](/programs/mastery) is a live program for leaders who've built their fundamentals. **Need strategic consulting support?** [Consulting and Advisory](/services/consulting) is for leaders who need personalized guidance beyond what a workshop can offer. **Want a keynote or conference session?** Jonathon also [speaks at conferences and events](/services/speaking) on practical AI adoption for non-technical audiences. --- ## Page: AI Keynote Speaker for Business and Nonprofit Leaders URL: https://upskailed.com/services/speaking # Speaking and Events Jonathon brings practical AI literacy to conferences, panels, and team events. His talks are designed for non-technical audiences who want to understand how AI can support their work and where to start. ## What to expect Jonathon's talks are practical, clear sessions designed for non-technical audiences. He helps people understand what AI can do for their work, what's getting in the way, and what changes when you learn to use it with intention. ## Formats Jonathon speaks in the format that fits your event. Each can be customized to your audience and theme. ### Keynote 30 to 60-minute talks on practical AI adoption, the "unknown unknowns" of AI capability, or what changes when leaders learn to work with AI deliberately. Customized to your audience and industry. ### Panel Discussion Jonathon brings a practical perspective to AI panels, keeping the conversation focused on what the audience can take away and use. ### Fireside Chat Conversational, audience-driven sessions that explore AI's real impact on work, leadership, and decision-making. Works well for smaller groups or more intimate event settings. ### Workshop Interactive, hands-on sessions (90 minutes to half-day) where participants work with AI tools in real time. Ideal as a conference add-on or standalone team event. Participants leave with workflows they built themselves. ## Topics - **The Unknown Unknowns of AI** — Most leaders don't realize what they're missing with AI. This talk reveals the gap between surface-level use and strategic partnership, and shows what changes when you close it. - **AI Without the Jargon** — A clear, practical introduction to what AI can actually do for non-technical professionals. No buzzwords, no fear tactics, and no "robots are coming for your job" framing. - **From Overwhelm to Implementation** — Why smart, capable people struggle with AI adoption, and the structured approach that turns scattered experiments into lasting workflows. - **AI for Nonprofits: Doing More With Less** — How nonprofit leaders are using AI to compress days of grant reporting into hours, stretch limited budgets further, and take on projects they previously couldn't justify the time for. - **Building With AI as a Founder** — How early-stage founders and entrepreneurs are using AI to compress timelines, take on work they'd otherwise outsource, and operate at a scale that used to require a bigger team. - **Custom Topics** — Have a specific theme or audience in mind? Jonathon develops talks tailored to your industry, audience, and event goals. ## Where Jonathon Has Spoken Jonathon has spoken at conferences, panels, and events across Canada on AI, entrepreneurship, and inclusive technology adoption. | Event | Organization | Format | Date | |-------|-------------|--------|------| | BlackNorth Initiative Entrepreneurship Mixer | BlackNorth Initiative | Panel | December 2025 | | ICON Advantage Symposium | ICON | Panel: Incubators, Accelerators and Startups | December 2025 | | BFUTR Global Tech Summit | Black Professionals in Tech Network | Panel: Future-Proofing Your Tech Career | November 2025 | | Canadian EdTech Accelerator Alumni Panel | Canadian EdTech Accelerator | Alumni Panel | November 2025 | | Elevate Festival — Black Innovation Zone | Elevate Festival, Black Innovation Zone | Panel: AI and Entrepreneurship | October 2025 | | DMZ BIP Rise and Pitch Breakfast | DMZ, Scotiabank | Panel: AI in Business and Inclusive AI | February 2025 | | AI Innovation at Black Career Conference | University of Toronto, Black Founders Network | Panel | January 2025 | | Black OW Virtual AMA Session | City of Toronto | Entrepreneurship AMA and Presentation | November 2024 | | ICON Advantage Symposium | ICON Talent Partners | Panel: Early Stage Startups | November 2024 | | Brampton Library Tech Talks | Brampton Library | Panel | February 2024 | | Take the Next Step Business Forum | NNMD Inc. | Panel | November 2023 | ## Invite Jonathon to speak at your event Tell us about your event and we'll get back to you within a few business days. ## Common questions ### How far in advance should we book? Four to six weeks is a comfortable lead time, though Jonathon has accommodated events with just a few weeks' notice. Include your timeline in the inquiry form and he'll let you know if it works. ### What are the speaking fees? Fees depend on the format, duration, travel, and how much customization is involved. Jonathon works with a range of budgets, from funded conferences to community organizations with limited resources. Share your budget range in the inquiry form and he'll let you know what's possible. ### Does Jonathon speak at virtual events? Yes. Virtual keynotes, panels, and fireside chats all work well over video. Workshops are strongest in person since participants are working with AI tools live, but Jonathon has run virtual workshops successfully for remote teams. ### Does Jonathon travel for events? Jonathon is based in Toronto and travels for events internationally. Include your event location in the inquiry form and he'll confirm availability. ### Can a talk be customized for our specific audience? Jonathon doesn't give the same talk twice. Before each engagement, he spends time learning about your audience, their industry, and what you want them to walk away with. The topics on this page are starting points. He builds from there. ### What A/V or technical setup is required? A microphone and a screen or projector for all sessions. Many of Jonathon's talks include live AI demonstrations, so a reliable connection between his laptop and the display matters. For workshops, participants need a laptop or tablet with wifi. Jonathon will share a full setup list once the format is confirmed. ### What's the difference between a workshop and a keynote? A keynote runs 30 to 60 minutes. The audience listens, watches live demonstrations, and leaves with new thinking about AI. A workshop runs 90 minutes to a half-day. Participants open their laptops, work with AI tools alongside Jonathon, and leave with workflows they can keep using. Workshops work well as conference add-ons or standalone team sessions. For organizations that want to go further, [Corporate Training](/services/corporate-training) offers multi-session programs built around your team's work. ## Also available **Want training for your team?** [Corporate Training](/services/corporate-training) delivers custom workshops built around your group's day-to-day work. **Need strategic consulting support?** [Consulting and Advisory](/services/consulting) is for leaders who need personalized guidance on AI strategy or workflows. --- ## Page: AI Programs for Business and Nonprofit Leaders URL: https://upskailed.com/programs # AI training that fits your schedule We offer three AI upskilling programs for non-technical leaders: asynchronous foundations, a live advanced cohort, and ongoing Think Tank support. Looking for team training? We do that too. ## AI Foundations Learn the fundamentals of working with AI through recorded lessons and hands-on exercises. Around 2-3 hours of content you can complete on your own schedule, using your own real work. The course is made up of four modules covering prompting, personas, research, and workflows. - **Price:** $399 CAD - **Price label:** One-time · Lifetime access - **Format:** Asynchronous - **Status:** Open - **Includes:** Certificate, 30-day guarantee - [Learn more](/programs/foundations) ## AI Mastery A live 6-week program for leaders who've built AI fundamentals and want to go further. Small group working sessions with Jonathon covering advanced AI collaboration, automation workflows, and guided implementation. Tentatively planned for June 2026. - **Price label:** Join the waitlist for details - **Format:** 6 weeks, live sessions, small group - **Status:** Waitlist - [Learn more](/programs/mastery) ## Think Tank A small, focused membership for professionals who want ongoing support as they apply AI in real work. Includes monthly office hours, a practical toolkit, members-only Q&A, and curated updates that help you stay current. - **Price label:** Annual membership - **Format:** Community membership, monthly office hours - **Status:** Waitlist - **Includes:** Capped at 25 members - [Learn more](/programs/think-tank) ## Team Training Custom AI training designed around your team’s day-to-day work. Workshops delivered virtually, in-person, or hybrid. We work with your group to build practical AI skills in context, not generic demos. - **Price label:** Custom pricing - **Status:** By request - [Learn more](/services/corporate-training) ## Not sure where to start? Tell us a little about where you are with AI and we'll send you a personalized recommendation. ## Common questions ### Do I need any technical background? Not at all. If you can use email and a web browser, you have all the technical skills you need to get started. ### What's the difference between Foundations, Mastery, and Think Tank? AI Foundations teaches the core skills: prompting, personas, research, and workflows. AI Mastery is a live 6-week program that goes deeper into advanced collaboration and implementation. Think Tank is a community membership for professionals who want monthly guidance and updates as they apply AI in day-to-day work. ### Can I expense this to my organization? Yes. We include an expense justification template with your enrollment that you can adapt for your manager or board. ### What AI tools will I need? To get full value, you'll need at least one paid AI subscription (around $20 - $30/month). Programs work with ChatGPT, Claude, Gemini, or others. You can also start with free tools and upgrade as needed. ### What's the refund policy? We offer a 30-day money-back guarantee on AI Foundations. If you haven't significantly advanced your skills after completing the course, email us for a full refund. ### When does AI Mastery launch? The program is tentatively scheduled for June 2026. Join the waitlist and you'll be the first to know once the exact dates are set. ## Also available **Need strategic guidance?** [Consulting and Advisory](/services/consulting) offers personalized work with Jonathon on your specific AI challenges and strategy. **Training for your organization?** [Corporate Training](/services/corporate-training) delivers custom workshops built around your team's actual work. --- ## Page: AI Foundations Course for Business and Nonprofit Leaders URL: https://upskailed.com/programs/foundations # AI Foundations Learn the fundamentals of working with AI through recorded lessons and hands-on exercises. Around 2-3 hours of content you can complete on your own schedule, using your own real work. No tech background needed. **Price:** $399 CAD (one-time · lifetime access) **Guarantee:** 30-day money-back **Status:** Enrollment open ## What you'll learn The AI Foundations course is made up of four modules covering the core skills you need to start getting real, consistent results from AI tools. Each module includes recorded lessons and practical exercises you complete with your own work, so everything you build is immediately useful. ### Module 1: Prompting and platform fluency How to communicate with AI clearly and get useful results. You'll learn practical prompting techniques, how to provide the right context, and how to evaluate which AI platform fits which task. By the end, you'll be able to sit down with any major AI platform and get it working for you. ### Module 2: Context, personas, and custom AI assistants How to build AI assistants that understand your role, your organization, and your style. You'll create reusable personas and projects that give you consistent, relevant results instead of starting from scratch every time you open a chat window. ### Module 3: Research and analysis How to use AI as a research partner. You'll learn workflows for deep research, synthesizing information from multiple sources, and turning a flood of data into clear, actionable insights. ### Module 4: Workflows and implementation How to move from one-off experiments to a way of working with AI that sticks. You'll design practical workflows for your recurring tasks, identify where AI creates the most value in your specific role, and build a plan for continuing to develop your skills after the course. ## Ready to get started? Enroll today for $399 CAD with lifetime access and a 30-day money-back guarantee. Have questions first? We're happy to help. - [Enroll now](https://learn.upskailed.com/checkout/ai-foundations) - [Get in touch](/contact) ## Common questions ### Do I need any technical background? Not at all. If you can use email and a web browser, you have all the technical skills you need to get started. ### What AI tools will I need? To take full advantage of the course, you'll need at least one paid AI subscription (around $20 - $30/month). Many participants start with free tools and upgrade after the first module. The course is designed to help you make the most of any major AI platform you have access to. ### How long does the course take to complete? The recorded content is around 2-3 hours total. Most people expect to complete it within a week while working at their own pace, but you have lifetime access, so there's no deadline. ### What if I've already been using AI on my own? Most participants have. The common experience is discovering how much more is possible with structured guidance. One participant told us they'd been using AI for months and called the first session a mindblower. ### Can I expense this to my organization? Yes. We include an expense justification template with your enrollment that you can adapt for your manager or board. ### What's the refund policy? We offer a 30-day money-back guarantee. If you haven't significantly advanced your skills after completing the course, email us for a full refund. ## Also available **Want to go deeper?** AI Mastery is a live 6-week program with small group sessions led by Jonathon. It picks up where Foundations leaves off. [Join the waitlist](/programs/mastery) **Need training for your team?** We design [custom workshops for teams and organizations](/services/corporate-training), built around your group's day-to-day work. --- ## Page: AI Mastery: Advanced Live AI Program for Leaders URL: https://upskailed.com/programs/mastery # AI Mastery An advanced program for leaders who've built their AI fundamentals and want to go further. Tentatively planned for June 2026, with six weeks of small group live sessions. **Format:** 6 weeks, live sessions, small group **Status:** Waitlist open ## What you'll cover AI Mastery picks up where Foundations leaves off. Where the fundamentals course teaches you how to work with AI effectively, Mastery focuses on how to apply those skills at a deeper level. Topics include advanced AI collaboration and automation workflows, emerging AI capabilities, and hands-on guided implementation. This is a live program, tentatively planned for June 2026, and will consist of six weeks of two-hour working sessions in a small group with Jonathon. ## Mastery is coming soon Join the waitlist and we'll let you know as soon as enrollment opens. - [Join the waitlist](https://forms.upskailed.com/mastery-waitlist) ## Common questions ### Do I need to complete AI Foundations first? It's the best preparation, but not a strict requirement. If you've spent meaningful time working with AI tools and are comfortable with prompting, personas, and basic workflows, you're likely ready. If you're unsure, reach out and we'll help you figure out the right starting point. ### How much time per week does this require? The live sessions are two hours per week for six weeks, and you should expect to spend some additional time working on your own challenges between sessions. ### What's the format? Live, interactive working sessions with Jonathon and a small group of peers. Each session builds on the last, so you'll leave with a cumulative set of skills and tools to apply to your work. ### How much does it cost? Pricing will be shared with waitlist members when it's finalized. We don't have a price to announce yet, so we'll share more details as we get closer to the launch. ### How big are the cohorts? The exact number will be confirmed when we launch, but the format is designed for a small group where everyone gets direct attention and meaningful interaction. ### When does it start? The program is tentatively scheduled for June 2026. Waitlist members will be the first to know once the exact dates are set. ## Also available **Starting from scratch?** If you haven't built your AI fundamentals yet, [AI Foundations](/programs/foundations) is the place to start. It's an asynchronous course you can complete on your own schedule. **Need training for your team?** We design [custom workshops for teams and organizations](/services/corporate-training), built around your group's day-to-day work. --- ## Page: Frequently Asked Questions | AI Training and Consulting FAQ URL: https://upskailed.com/faq # Frequently Asked Questions Answers to the questions we hear most. If yours isn't here, [get in touch](/contact) and we'll help you figure it out. ## Getting Started ### Is this for me if I'm not technical? 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. ### How do I know which offering is right for me? 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 we'll help you figure it out. ### What if I've already been using AI on my own? 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. ## Tools and Skills ### What AI tools do I need? 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 (roughly $25/month) gives you the best experience, but you can start with free versions. There's no required software beyond that. ### Will what I learn become outdated as AI changes? 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. ### Do you teach people how to use AI for specific tasks? 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. ## About the Training ### How much time does this take? AI Foundations is an asynchronous course with roughly 2-3 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. ### Who teaches the program? 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. ### What's the difference between the programs and the services? 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. ## About the Think Tank ### What is the Upskailed Think Tank? 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. ### Who is the Think Tank for? 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. ### How is the Think Tank different from Foundations and Mastery? 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. ## About Upskailed ### What makes Upskailed different from other AI training? 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. ### Will this help? 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. ### I work in the nonprofit sector. Is this relevant to me? 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. ## Practical Details ### How much does it cost? 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. ### Is my data safe when using AI tools? 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](/privacy). ### What if I have a question that's not answered here? [Get in touch](/contact). Jonathon typically responds within 2-3 business days. There's no obligation and no sales pitch. --- ## Page: Upskailed Think Tank Membership for AI Professionals URL: https://upskailed.com/programs/think-tank # Think Tank Ongoing advisory, tools, and peer support for professionals working with AI. Stay current without tracking every new release yourself. ## Description The Upskailed Think Tank is a small, focused membership for professionals who have built their foundational skills and want ongoing support as they put them to work. Members get monthly live sessions, a library of prompts and workflows, a members-only Q&A space, and a curated feed of developments worth paying attention to. New tools appear constantly, capabilities expand, and what worked three months ago may no longer be the best approach today. The Think Tank keeps you current so you don't have to track it all yourself. Membership is capped to keep the group small enough that office hours feel personal. ## What's included ### Monthly office hours Live group sessions with Jonathon where you can bring questions, troubleshoot workflows, pressure-test ideas, and keep pace as new capabilities emerge. ### The Toolkit A prompt library and workflow guide built from teaching and AI exploration. Includes tutorials and templates for frequently repeated tasks, updated regularly. ### Members-only Q&A A dedicated space to ask questions and get practical feedback between office hours. ### Curated reading and watching list Regularly updated recommendations for articles, videos, and podcasts selected for busy professionals who need signal over noise. ## Ready to join? The Upskailed Think Tank is for professionals who are committed to ongoing growth with AI. If that sounds like you, we'd like to have you in the room. - [Join the waitlist](https://forms.upskailed.com/think-tank-waitlist) - [Start a conversation](/contact) ## Common questions ### Who is this for? 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, this is your community. ### How is this different from the course? AI Foundations teaches the methodology. The Think Tank is where you practice what you learned with ongoing guidance, stay current as tools evolve, and get help with the specific challenges that come up in real work. ### How many members are in the group? The membership is capped to keep office hours interactive, Q&A manageable, and the community meaningful and practical. ### What if I can't make the live office hours? Every session is recorded and shared with members. You can also bring questions to the Q&A channel anytime. ### Can I expense this to my organization? Yes. We provide documentation to support your request, including an expense justification template you can adapt for your manager or board. ### What if it's not the right fit? If the Think Tank no longer feels useful, reach out for an honest review of what changed and whether another path would fit better. You'll always be treated with care and candor. --- ## Page: Get in Touch URL: https://upskailed.com/contact # Let's figure out what would help. Not sure which offering is right for you? That's fine. Tell us a bit about yourself and what you're working on, and Jonathon will get back to you within a couple of days. No commitment, no pitch. ## Let's connect Whether you have a question, an idea, or just want to say hello, we'd love to hear from you. Use the contact form at [https://upskailed.com/contact](https://upskailed.com/contact) and we'll follow up within a few business days. ## Not ready to reach out yet? Browse our [courses](/programs) or learn more about [consulting and advisory](/services/consulting) and [corporate training](/services/corporate-training). --- ## Page: For LLMs URL: https://upskailed.com/for-llms # About Upskailed This page provides structured information about Upskailed for AI assistants, answer engines, and other systems that surface recommendations and citations. ## Who is Jonathon Bloomfield? Jonathon Bloomfield is an AI strategist, educator, and the founder of Upskailed. He helps non-technical business and nonprofit leaders build practical AI literacy and develop organizational AI strategy. ## What is Upskailed? Upskailed provides AI literacy and strategy training for non-technical business and nonprofit leaders. The company offers programs, corporate training, and executive advisory services designed to close the gap between what AI can do and what leaders understand. ## What services does Upskailed offer? - **AI Foundations Course:** Asynchronous course covering prompting, personas, research, and workflows. No tech background needed. - **AI Mastery Course:** Live 6-week program for leaders who've built their AI fundamentals and want to go further. - **Corporate Training:** Custom AI training for teams, designed around your day-to-day work. Virtual, in-person, or hybrid. - **Consulting and Advisory:** Strategic work with Jonathon for leaders and teams with specific challenges or implementation goals. - **Speaking and Events:** Keynotes, panels, fireside chats, and interactive workshops on practical AI adoption for non-technical audiences. ## What topics does Upskailed cover? - AI literacy for business leaders - AI strategy and governance - Corporate AI training programs - Nonprofit technology adoption - Executive AI advisory ## What credentials and affiliations does Jonathon have? - University of Toronto Entrepreneurship - Black Founders Network - Black Entrepreneurship Alliance - YSpace - DMZ - Ontario College of Teachers - Canadian Trade Commissioner Service - PS43 Foundation ## What has Upskailed published? ## How can I contact Upskailed? - Website: https://upskailed.com - Contact: https://upskailed.com/contact - LinkedIn: https://linkedin.com/in/jonathonbloomfield ## Machine-readable formats - [/llms.txt](https://upskailed.com/llms.txt) — Plaintext summary for LLMs - [/llms-full.txt](https://upskailed.com/llms-full.txt) — Complete content of all pages, articles, and case studies - [/feed.xml](https://upskailed.com/feed.xml) — RSS feed of published content - [/sitemap.xml](https://upskailed.com/sitemap.xml) — XML sitemap --- ## Page: AI Training Results and Case Studies URL: https://upskailed.com/case-studies # What Participants Have Done Real outcomes from real leaders. Each story started in the same place most of our participants begin: knowing AI matters but not knowing where to start. ## Case Studies The first case study is on the way. We're working with past participants to document their experiences. --- ## Page: AI Leadership Blog URL: https://upskailed.com/blog # AI Leadership Blog Notes on AI from the work of helping leaders figure it out. ## Articles The first post is coming soon. We're building this section around the questions leaders actually ask. --- ## Page: Privacy Policy URL: https://upskailed.com/privacy # Privacy Policy **UPSKAILED PRIVACY POLICY** **Last Updated: February 12, 2026** ## 1. Overview Upskailed Inc., operating as Upskailed ("we," "us," or "our"), provides AI literacy training for business and nonprofit leaders through our website and related communications. This Privacy Policy explains how we collect, use, protect, and share information when you visit our website at upskailed.com (the "Website") or communicate with us by email. Please read this policy before submitting any information through the Website. If you have questions about this policy, please contact us at privacy@upskailed.com before submitting any personal information. ## 2. Information We Collect We collect information in three ways: **Information you provide directly** When you submit a form on our Website (such as a contact form, inquiry form, or course enrollment form), we collect the information you enter. This typically includes your name, email address, and the content of your message. Some forms may ask for your organization name, professional role, or other details relevant to your inquiry. All form fields marked as optional are truly optional. When you subscribe to our newsletter, we collect your name and email address. **Information collected automatically** We use Plausible Analytics, a privacy-focused analytics tool that does not use cookies, does not collect personal data, and does not track individual visitors. Plausible provides us with aggregate information about how people use our Website (such as which pages are visited and how visitors find us) without identifying anyone individually. We use Vercel Analytics for website performance monitoring. Vercel Analytics collects aggregated performance data without cookies or personal identification. **Information collected by third-party services** Our forms are powered by Tally, a third-party form provider. When you submit a form, your response passes through Tally's infrastructure. Tally's privacy practices are governed by their own privacy policy, available at [tally.so/help/privacy-policy](https://tally.so/help/privacy-policy). Our newsletter is managed through Loops, an email platform. When you subscribe, your name and email address are stored by Loops to facilitate delivery. Loops' privacy practices are governed by their own privacy policy, available at [loops.so/privacy](https://loops.so/privacy). ## 3. How We Use Your Information We use the information we collect to: - Respond to inquiries and messages submitted through our contact and inquiry forms - Send our newsletter to subscribers who have opted in - Understand how visitors use our Website in aggregate (through anonymous analytics) - Improve our Website and services - Fulfill any legal obligations We will not use your personal information to contact you for reasons unrelated to your inquiry or subscription. We do not sell personal information to third parties. ## 4. Newsletter and Email Communications Our newsletter is sent to subscribers who have explicitly opted in by entering their name and email address in the newsletter signup form. In accordance with Canada's Anti-Spam Legislation (CASL): - Subscribing to the newsletter is voluntary and requires your explicit consent - Every newsletter includes a clear and functional unsubscribe link - Unsubscribe requests are processed promptly - We do not add email addresses to our newsletter list from other sources (such as contact form submissions) without separate, explicit consent ## 5. Cookies and Tracking We do not use tracking cookies on our Website. Plausible Analytics operates without cookies. Vercel Analytics operates without cookies. No personal data is collected through either analytics service. Tally, our form provider, may set functional cookies when you interact with an embedded form. These cookies are necessary for the form to function and are governed by Tally's cookie policy. We do not use any advertising trackers, retargeting pixels, or social media tracking scripts. ## 6. Legal Basis for Processing We process your personal information on the following bases: - **Consent:** When you submit a form or subscribe to our newsletter, you consent to our use of that information for the stated purpose. - **Legitimate interest:** We use anonymous analytics to understand Website usage and improve our services. This does not involve personal data. ## 7. Accessing, Correcting, and Deleting Your Information You have the right to access, correct, or delete your personal information. To make a request, please email privacy@upskailed.com. - **Form submissions:** We can provide copies of your submissions, correct inaccuracies, or delete your submissions from our records. - **Newsletter:** You can unsubscribe at any time using the link in any newsletter, or by emailing privacy@upskailed.com. - **Analytics:** Our analytics tools do not collect personal data, so there is no personal information to access, correct, or delete. We will respond to requests within 30 days. ## 8. Data Retention - **Form submissions** are retained for up to 24 months or until you request deletion, whichever comes first. - **Newsletter subscriptions** are maintained until you unsubscribe. - **Analytics data** is aggregated and contains no personal information. - We retain any information required by applicable law for the duration required. ## 9. Data Security Your information is stored electronically using industry-standard infrastructure. Our Website is hosted on Vercel. Form data is stored by Tally. Newsletter data is stored by Loops. Each of these services maintains its own security practices and certifications. We take reasonable steps to protect information submitted to us, but no system is completely secure. If you have concerns about submitting information electronically, please contact us at privacy@upskailed.com to discuss alternatives. ## 10. Data Storage Location Our service providers (Vercel, Tally, Loops) may store data on servers located outside of Canada, including in the United States. By submitting information through our Website, you acknowledge that your information may be processed in jurisdictions with different privacy laws than Canada. ## 11. Security Breaches In the event of a breach affecting your personal information, we will notify affected individuals within a reasonable timeframe and take appropriate steps in accordance with applicable Canadian privacy laws. ## 12. Use of Our Website by Minors Our Website and services are designed for adult professionals. We do not knowingly collect information from anyone under the age of 18. If we become aware that we have collected information from a minor, we will delete it promptly. ## 13. Disclosure of Personal Information We may share your personal information in the following circumstances: - **Service providers:** We share information with the third-party services described in Section 2 (Tally, Loops, Vercel, Plausible) to operate our Website and services. - **Legal requirements:** We may disclose information when required by law, regulation, or legal process. - **Business transfer:** If Upskailed or its assets are acquired or transferred, personal information may be among the transferred assets. We would notify affected individuals before any such transfer. We do not sell, rent, or share personal information with third parties for their marketing purposes. ## 14. Third-Party Services Our Website relies on the following third-party services, each with their own privacy practices: | Service | Purpose | Privacy Policy | |---------|---------|---------------| | Tally | Form submissions | [tally.so/help/privacy-policy](https://tally.so/help/privacy-policy) | | Loops | Email and newsletter delivery | [loops.so/privacy](https://loops.so/privacy) | | Plausible Analytics | Website analytics (no personal data) | [plausible.io/privacy](https://plausible.io/privacy) | | Vercel | Website hosting and performance analytics | [vercel.com/legal/privacy-policy](https://vercel.com/legal/privacy-policy) | ## 15. Changes to This Policy We may update this policy from time to time. If we make changes we consider significant, we will note the updated date at the top of this page. We encourage you to review this policy periodically. ## 16. Contact Us If you have questions about this policy or how we handle your information, please contact us at privacy@upskailed.com. We will respond within 7 business days. # All Published Articles Articles are coming soon. # All Case Studies Case studies are being developed with participant permission.