--- title: "AI Consulting for Professionals | Consulting and Advisory" description: "Strategic AI consulting with Jonathon Bloomfield: workflow design, organizational strategy, grant writing, and advisory. Virtual across Canada and the U.S." canonical_url: "https://www.upskailed.com/services/consulting" md_url: "https://www.upskailed.com/services/consulting.md" last_updated: "2026-08-06" --- # Consulting and Advisory Strategic work with Jonathon for professionals who need more than a course. Focused sessions on your specific challenges, from workflow design to organizational strategy to implementation coaching. At a glance: focused working sessions, starting with a free intro conversation. Engagements run from two or three sessions to several months, with retainer advisory available. Investment is scoped per engagement. ## What to Expect Consulting is entirely shaped by your situation. There’s no syllabus — you bring the challenges, and Jonathon works through them with you: designing workflows, setting strategy, or coaching implementation. It starts with a free, informal conversation. If there’s a fit, you get a clear proposal — what you’ll work on, how many sessions, what it costs, and what you’ll walk away with. ## What You Can Work On - **AI workflow design** (research · content · operations). 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** (leadership teams · boards). 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** (nonprofits · funded programs). 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** (hands-on · practical). For professionals 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** (retainer basis). Continued access to Jonathon on a retainer basis. Monthly or quarterly sessions, depending on what you need. Useful for professionals rolling out AI across their organization who want a sounding board as new challenges come up. ## How It Works ### 01. 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. ### 02. 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. ### 03. Working sessions This is where things get built. 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. ### 04. 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 professionals who would like continued access, ongoing advisory is available on a retainer basis. > "I’d been experimenting with AI for months on my own and wasn’t getting anywhere meaningful. After three sessions with Jonathon, I had workflows I actually used every day. The difference was having someone who understood my work, not just the technology." — Nonprofit director · Consulting client ## Common Questions **Who is consulting for?** Professionals 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 teams who spend large portions of their time on funding applications. **What is the ongoing advisory retainer?** For professionals 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. ## Also Available **Corporate Training** (for teams): Designed for groups — Jonathon builds a custom program around your team’s day-to-day work. [Explore training](/services/corporate-training) **AI Foundations** (self-paced): Want the fundamentals first? A self-paced course you can complete on your own schedule. [Explore the course](/programs/foundations) [Start a conversation](/contact) ## Sitemap - [Browse every markdown page](/sitemap.md) - [Read the concise site summary](/llms.txt) - [Read the complete site content](/llms-full.txt)