The 90-Day AI Playbook | ChiefAIOfficer.com × Scaling Up
Live Working Session · May 21, 2026
Free CEO Working Session
Thursday · May 21, 2026 · 1pm ET

The 90-Day
AI Playbook.

A working session for CEOs and senior executives who want AI on their P&L, not in their pile of stalled pilots.

75 Minutes Live Free
Reserve Your Seat
01

Every CEO is under pressure to do something with AI.

Investors are asking. Competitors are claiming. Employees are already running company data through tools they signed up for themselves.

And almost none of it is producing a number you can point to on your P&L.

The problem isn't the technology. The same tools that stall at most companies are working fine at the ones that win. The difference is how it gets rolled out.

02

A plan you can act on within seven days. No tech talk. No vendor pitch. No coding.

In 75 minutes, Chris Daigle walks you through the same operating model his firm uses with $20M to $200M companies across construction, professional services, manufacturing, and PE-backed businesses.

i.

The $50K Problem Filter

A four-question test to find the workflow in your business that should be your first AI pilot.

ii.

The 90-Day Operating Model

A quarterly cadence the CEO runs, not IT — with the four roles every AI initiative needs.

iii.

The CRIT Prompting Framework

Demonstrated live on a real executive task. Gets you into the top 5% of AI users in one session.

iv.

A Starter AI Use Policy

The governance document most growing companies don't have, in plain English.

v.

A 7-Day, 30-Day, 90-Day Plan

Exactly what to do Monday morning so your pilots don't end up in the same graveyard as everyone else's.

03
Built for the leaders, not the lab.

This Session Is For

  • CEOs, COOs, CFOs & senior leaders At $20M–$200M US companies
  • Operators tired of AI talk Who want a way to actually run it
  • Especially useful If you run on Scaling Up, EOS, or Rockefeller Habits
04
Chris Daigle
Chris Daigle
Founder & CEO, ChiefAIOfficer.com

Author of The Chief AI Officer Blueprint. Board member of the International Association of Chief AI Officers. Host of Using AI at Work, a top 5% global business podcast.

His firm runs 90-day AI transformation engagements with growing companies in construction, professional services, manufacturing, and PE-backed industries.

18,000+ Non-technical executives trained
YPO · Vistage Hundreds of members coached
Top 5% Global business podcast
05
Date
Thursday
May 21, 2026
Time
1:00 pm ET75 minutes incl. Q&A
Cost
Free
Replay
Sent to all
registrants
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You'll get the live session, the Q&A, the replay, and the worksheet pack.

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A working session, not a webinar.