For CEOs and EDs of mission-first organizations

Crossing from AI Anxiety to Imagination.

A two-hour session for leaders of sub-$5M nonprofits and mission-driven organizations who are done watching AI happen around them — and ready to move with it.

Apply for the cohort Free starter kit ↓
Session Details
$299
Per person — invoiced after confirmation
8–12
Leaders per cohort — intentionally small
2 hrs
On Zoom, plus two-week follow-up
Now
Cohort forming — spots limited
Who this is for

You run a lean org. You don't have time for theory.

LeadAI is built for CEOs and EDs of nonprofits and mission-first businesses with budgets under $5M. That's an underserved market in the AI training space — most programs assume you have a tech team, an innovation budget, or unlimited time to experiment.

You have none of those. What you have is real work, real accountability, and a growing gap between where you are on AI and where your funders and board expect you to be.

This session is peer-only. No consultants selling a platform. No enthusiasts pitching theory. A guide who runs an org your size and built this inside his own leadership — not as a technologist, but as a CEO with the same pressures you have.

01
You've opened ChatGPT. You weren't sure what to ask. You closed it. The anxiety isn't about technology — it's about falling behind in front of the people whose opinion of your leadership matters most.
02
A funder has asked about your AI strategy. You gave a vague answer. You don't want that to happen again — especially not in a board conversation.
03
Your staff knows more than you do — or you're so far ahead they can't follow. Either way, there's no system. Nothing survives you leaving the room.
04
You've sat through the webinars. Nothing connected to your actual work. You need something built, not something explained.
What this looks like in practice

I didn't theorize this. I built it inside my own org.

These are real examples from Aaron's work as CEO of UpStart — a nonprofit with a real budget, real staff, and real accountability to funders and a board.

Fundraising
The Interim Chief Advancement Officer
When we were between Chief Advancement Officers, I didn't slow down and post the job. I built an Interim CAO — a configured AI that understood our fundraising pipeline, knew our major donors by name, and could help me draft outreach, pressure-test proposals, and think through strategy when no one else was available. It held the role until we hired.
Financial Oversight
The Director of Finance
I now have a Director of Finance that reviews our monthly reports and flags inconsistencies. It doesn't replace our finance team — it makes me a sharper reader of the work they bring me, and it catches things before they surface in an awkward board conversation.
Governance
The Board Governance Partner
I have a governance partner that tracks board member commitments across meetings, drafts follow-up emails, and prepares me for conversations I used to handle on memory and a messy Google Doc.
Fundraising — what funders are noticing
AI as a line item in a grant proposal
I included an AI agent as a named line item in a grant proposal — listed under staffing, because that's what it is. The funder didn't blink. They asked how it worked. None of this required technical skill. It required thinking about the work differently.
What you walk away with

Not a framework. Something operational.

01
A working AI setup
Account configured, settings dialed in, Projects built and ready to use before you log off. Not a demo — something operational in your actual leadership context.
02
One real AI role built
An interim staff function, a board governance agent, or a workflow tuned to your highest-leverage need. You define it. We build it together during the session.
03
A draft AI governance policy
A board-ready document you leave with and adapt. Not homework you do later — something you can bring to your next board meeting.
04
Your blockers named
The specific places inside your org where adoption gets stuck — and a clear enough path forward that the next step doesn't feel abstract.
05
A peer cohort
8–12 leaders navigating the same thing. Small enough that the room actually exhales together.
06
A two-week follow-up
The cohort reconnects two weeks later — not to recap, but to share what actually happened when you brought it back to your org. That accountability is what separates this from every session you've forgotten.
A framework for this moment

Naaseh v'nishma.

We will do and we will hear. Action and listening bound together — not sequential.

"The move isn't fearlessness. It's choosing to learn through doing, while staying awake to what the doing reveals."
The Jewish principle of naaseh v'nishma — Israel's declaration at Sinai — is often read as a leap of faith. The deeper teaching is in the structure: you don't act and then stop listening. You act and listen harder. Nobody fully understands what we're in the middle of right now — not the enthusiasts, not the skeptics. Naaseh v'nishma doesn't ask you to abandon caution. It asks you to bring caution with you into action.
Part One
Name the thing
We start by saying out loud what you haven't said anywhere else. The anxiety, the confusion, the gap between where you are and where you think you should be. The room exhales. That's when learning can start.
Part Two
Build something real
You don't leave with a framework. You leave with something you built — a working AI workflow inside your actual leadership context. Whatever your highest-leverage use is, we build it together.
After
Stay in motion
Two weeks out, the cohort reconnects — not to recap, but to share what actually happened when you brought it back to your org. That accountability is what separates this from every other session you've attended and forgotten.
Who's teaching it

A peer who figured it out. Not a consultant who theorized it.

Aaron Katler is the CEO of UpStart, a nonprofit innovation organization working with 150+ organizations across North America. He has been building AI-enabled tools into his own leadership practice for two years — not as a technologist, but as a CEO with the same pressures, stakeholders, and resource constraints you have.

He is not selling a platform or a consulting engagement. He is sharing what actually worked — inside a real organization with a real budget and real accountability.

CEO, UpStart — Jewish social innovation organization, 150+ partner organizations across North America
Founder, APK Ventures — advisory and methodology work in the AI adoption space
Two years building AI infrastructure inside a sub-$5M nonprofit — not theorizing it
The tools he teaches are the same ones he uses every day — built in Claude, tested in real work
"
I didn't set out to build a session. I started doing this in my own work, and enough people asked how that I decided to run a small group.
Aaron Katler · CEO, UpStart
Free resource

The NFP Leader's AI Starter Kit

Not ready to apply for the session yet? Start here. This free guide gives you the platform map — what each AI tool actually contains and what to use it for — plus the 25 terms every nonprofit leader needs to understand before the next funder conversation.

It's the terrain map. The full scaffold ($49) gives you the sequence.

✓
Complete platform comparison: Claude, ChatGPT, Copilot, Gemini, Perplexity
✓
Tool-by-tool breakdown — what each one does and when to use it
✓
The starter stack recommendation for sub-$5M organizations
✓
Glossary of 25 AI terms — plain language, no jargon
✓
Free — share with your board, your team, your peers
The full guide

The NFP Leader's AI Scaffold

The Starter Kit shows you the terrain. The Scaffold gives you the sequence — what to build first, what to build next, and how to move your team without losing what you built.

Thirty days. Three phases. Built for CEOs and EDs of sub-$5M organizations who don't have a tech team and can't afford to experiment indefinitely.

✓
Phase-by-phase 30-day implementation sequence
✓
Three complete AI Project prompt templates — Executive Coach, Adoption Consultant, and your highest-leverage role
✓
Board-ready AI governance policy starter
✓
Glossary of 25 terms — plain language, ready to share
✓
30-day implementation checklist
$49
One-time — instant PDF download
✓
13-page implementation guide
✓
Prompt templates, governance policy, checklist
✓
Discount codes available for cohort members
Get the Scaffold →
Secure checkout via Stripe. PDF delivered immediately after payment.
Apply for the cohort

This cohort is intentionally small.

8–12 leaders per session. Peer-only — no consultants, no vendors. Application-based because the room matters as much as the content.

You will hear back within 48 hours. If accepted, you'll receive a pre-work email and a calendar invite. The session runs two hours on Zoom, followed by a two-week cohort check-in.

Format
Zoom, cohort-based
Duration
~2 hours + follow-up
Cohort size
8–12 leaders
Investment
$299 per person
Status
Now forming
Platform
Claude Pro (included guidance)
Request your spot
A few questions to make sure it's the right fit for you and for the room.
$299 per person — invoiced after confirmation. You'll hear back within 48 hours.
You're in the queue.
Aaron will be in touch within 48 hours to confirm your spot and send pre-work. Space is limited — thanks for moving quickly.