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Upskailed

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

StructureFocused working sessions
First stepFree intro conversation
Scope2–3 sessions to several months
ContinuityRetainer advisory available
InvestmentScoped per engagement
Start a conversation

No pressure, no pitch.

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

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.

Research · Content · Operations

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.

Leadership teams · Boards

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.

Nonprofits · Funded programs

Implementation coaching

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.

Hands-on · Practical

Ongoing advisory

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.

Retainer basis

How it works

  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.

  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.

  3. 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.

  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 professionals who would like continued access, ongoing advisory is available on a retainer basis.

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.
Nonprofit director · Consulting client

Let’s talk about what you’re working on

Scoped per engagement

Share a bit about your situation and Jonathon will set up an intro conversation. No pressure, no pitch.

Common questions

Also available