V1 · Founding Cohort · 5 Spots Only · Cohort 1 · 22.06.2026

You don't have a
tools problem.
You have a thinking problem.

A 90-day 1:1 coaching programme for mid-to-senior corporate leaders who want to lead AI change, not just survive it.

Apply for a Founding Spot → Take the Free AI Readiness Assessment

Mindset Shift Guarantee - full refund if you don't see genuine results

Built by a practising CIO 18 years enterprise experience CoPilot rollout to 400-person org

The Problem

Every AI tool training
misses the point.

Your team is using AI.
You're not sure you are.And that gap is growing every week.

You're being asked about AI strategy.
You don't have one.And everyone's watching.

Everyone else seems confident.
You're quietly worried.That's the part nobody talks about.

The CIO Playbook is the only programme that closes this gap, by changing how you think, not just what tools you click.

Who It's For

This is built
for you if…

You're senior enough to need an answer, close enough to the ground to feel the pressure. This is for leaders who are done waiting for IT to hand them a strategy.

This is NOT for you if…

This programme requires genuine commitment, not passive consumption. It's built around doing, not watching.

Free Diagnostic · No Commitment

Not sure where you stand?
Find out in 5 minutes.

Take the free AI Readiness Assessment, a short diagnostic showing you exactly where you sit across the 4Rs and your biggest gap. No commitment required. Instant results.

Take the Free AI Readiness Assessment →

Takes 5 minutes · Free · No email required to get results

The Signature Framework

The 4R Method

The only AI leadership framework built by someone who has actually done it at enterprise scale, teaching leaders to think in systems, not just use tools.

01
Reframe

Cut through the hype and fear with a clear mental model of what AI actually is and isn't. Replace anxiety with clarity.

02
Rethink

Look at your role, team, and processes differently, where does AI change what you do, not just how you do it?

03
Redesign

Apply systems thinking to your workflows. Map your data, find AI leverage points, redesign processes from first principles.

04
Represent

Become the AI champion in your organisation. Drive adoption upward and outward with confidence and credibility.

The Secret Sauce: Most AI programmes skip straight to tools. The 4R Method builds the thinking layer first, because without that, no tool will save you.

What's Included

Everything you need to go from anxious to champion

A complete 90-day system - coaching, support, frameworks, and tools, designed to build genuine AI leadership capability, not just surface-level confidence.

Founding Client Investment
$3,000 SGD

Total perceived value: $7,100 SGD
Price rises to $5,000 SGD after 5 founding spots are filled.

12 Weekly 1:1 Coaching Calls (90 days) $3,600 SGD
WhatsApp Support Access (90 days) $1,500 SGD
4R Method Workbooks & Homework Materials $800 SGD
BonusAI Champions Toolkit $500 SGD
BonusThe CIO's AI Briefing Template $300 SGD
BonusThe Process Redesign Workbook $400 SGD
Total Perceived Value $7,100 SGD
Founding Client Investment $3,000 SGD
Apply for a Founding Spot →

Mindset Shift Guarantee - full refund if you don't see genuine results

The Coach

Built by someone who's actually done it.

Ben Westlake — CIO and founder of The CIO Playbook
18
Years in tech leadership
400
Person CoPilot rollout led
90
Days to genuine mindset shift

Ben Westlake is a practising CIO with 18 years of enterprise technology leadership. He led the Microsoft CoPilot rollout across a 400-person organisation, and built the 4R Method from that lived experience, not theory.

The only AI leadership framework built by a practising CIO, not a consultant who read a book, not a theorist with a deck.

The Redesign phase - systems thinking + data, is the differentiator no other programme comes close to offering.

Teaching leaders to think in systems, not just tick a course completion box.

18 years inside enterprise organisations means Ben understands the politics, pressures, and real constraints you're working inside, not an idealised version of them.

5 Founding Spots. One Start Date.

Cohort 1 kicks off 22 June 2026. There are 5 founding spots at $3,000 SGD. Once they're gone, the price rises to $5,000 SGD permanently and this cohort closes.

Spots remaining: 5 of 5
5 Spots Only Cohort Starts 22 June Price Rises After Cohort 1
Apply for a Founding Spot →

The Mindset Shift Guarantee

"Show up, do the work, engage with every phase of the 4R Method, and if you don't see a genuine mindset shift by the end of 90 days, I'll refund you completely."

No risk. Just commitment.

Common Questions

Before you apply

The questions most people have before they take the next step.

Courses teach you what tools exist. The CIO Playbook changes how you think. It's 1:1, built around your specific role, team, and organisation, not a generic curriculum you watch at 1.5× speed. The 4R Method applies systems thinking to your actual work, not a hypothetical case study.
Using tools and leading AI change are completely different things. Most leaders who come to The CIO Playbook already use ChatGPT or CoPilot, they're stuck because they can't build a coherent strategy, can't redesign their team's workflows, and can't credibly represent AI upward. That's what this solves.
One 60-minute coaching call per week, plus roughly 1–2 hours of applied work between sessions. The work is designed to slot into your existing role, you're not building something separate, you're applying the 4R Method directly to the work you're already doing. Most clients say the sessions alone change how they show up in their day-to-day.
Yes, and many clients use their L&D or professional development budget. The investment is $3,000 SGD, which sits well within most corporate development budgets. If you need an invoice or formal proposal for approval, we can provide one after your application is accepted.
You'll answer 3 short questions about your role and what you're trying to solve. Ben will review your application and reach out within 24 hours to schedule a quick 20-minute discovery call, no pressure, no pitch. If it's a fit, you'll receive your onboarding details and secure your founding spot before Cohort 1 closes.
The Mindset Shift Guarantee is simple: show up, do the work, engage with every phase of the 4R Method, and if you don't see a genuine shift in how you think about and lead AI in your organisation, you'll receive a full refund. No awkward conversations. No conditions beyond genuine participation.

Ready to Lead?

Ready to become the AI champion
your organisation needs?

$3,000 SGD · 5 Founding Spots · Cohort Starts 22 June 2026

Apply for a Founding Spot →

What happens after you click

1
Apply

Answer 3 short questions about your role and what you want to change

2
Discovery Call

Ben reviews your application and reaches out within 24 hours for a 20-min call

3
Secure Your Spot

If it's a fit, you receive onboarding details and lock in your founding rate

4
Cohort Kicks Off

22 June 2026 — your 90-day transformation begins