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Upskailed

For Leaders

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.

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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 you can work on

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.

What clients say

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.

ND
Nonprofit director

Let's talk about what you're working on

Share a bit about your situation and we'll set up an intro conversation. No pressure, no pitch.

Common questions

Also available

Looking for team training? Corporate Training is designed for groups and teams. Jonathon builds a custom program around your team's day-to-day work.

Want to start with the fundamentals first? AI Foundations is an asynchronous course you can complete on your own schedule, and AI Mastery is a live program that goes deeper.