Live cohort · 4 weeks · Kicks off Monday, June 22

Build daily Claude habits into how you lead.

A live 4-week cohort for senior leaders. Run the CEO OS V3 journey with Matt Kesby, plus 1:1 working sessions with Anita, your AI facilitator.

13 languagesMatt Kesby + Anita AI● MCP receipts
Your cohort1:1 with Anita
AI
Anita · AI Facilitator
● Ready · talk in real time

Velocity Forum Kick Off Session — Mini deck — Part A

Do the real task with Anita. Ship the artifact, install the Skill.

Skills installed
9
Value impact
Measured

Why traditional training fails

Most leaders try AI once and drift back.

You opened Claude. You asked it something. It was interesting. Then your week swallowed you whole and the tab stayed closed.

  • You experiment in spare moments, never on the work that matters most.
  • Board prep, briefings, and risk reviews still eat your evenings.
  • You know AI should change how you operate, but no habit ever sticks.
  • Generic prompts give generic answers, so you stop trusting them.

The gap is reps, not knowledge.

Reading about AI does not change how you run a week. Doing real work with it does. This cohort is built around the reps.

Knowledge retention over time

100%50%0%Day 0Day 7Day 30TraditionalWith Velocity

Weekly Value Impact

Anonymised average · Recent cohort

Sample week

Value Impact

Every session leaves a *receipt.*

You don't just learn. You produce. Each activity logs a Value Impact receipt so the gains are visible, not vague.

  • A real artifact you keep from every session.
  • Skills installed in Claude CoWork that you own forever.
  • A clear record of where the time went back into your week.

What you walk out able to do.

Board prep

Walk in ready

Turn raw context into a sharp board pack and the questions to expect, with Claude doing the heavy lifting.

Briefings

Brief in minutes

Draft executive briefings that say more in less, so your team reads them and acts.

Risk

See it early

Run an operations risk scan that surfaces what you'd otherwise catch too late.

Routine

A working week

Leave with a Claude routine built into how you draft, decide, and think every day.

Made for the people who actually decide.

This cohort is shaped for experienced leaders who run real weight, across the industries and roles they already lead in.

Industries

B2B (general)Boutique HotelsConstructionFintechManufacturingProfessional servicesSaaSEnergyFinanceAccounting & BookkeepingCivil EngineeringCommercial ConstructionCommercial Real EstateFinancial PlanningInsuranceLegal ServicesMarketing & Creative AgenciesProperty ManagementRecruitment & StaffingResidential BuildingStrata & Body CorporateTrades & Home ServicesTechnologyManagementCorporateConsultingmanagement consultingEnterprise

Roles

ExecutiveCEOFounderOperationsSalesAccount ExecutiveAccount Executive (AE)ConciergeExecutive OfficerLeasing AgentProcurementProperty ManagementSales ManagerSales Development Rep (SDR)

Works with the tools you already run

Built around Claude CoWork.

Claude CoWork

Live sessions presented in

Human coachEnglish

1:1 with Anita · available in 13 languages

ArabicChinese (Mandarin)DutchEnglishFrenchGermanHindiIndonesianItalianJapaneseKoreanPortugueseSpanish

Live humans for momentum. Anita for the reps.

A human coach opens the cohort and holds you accountable. In between, you do the real work 1:1 with Anita on your own problems.

Human-led

Kick-Off & Accountability

Matt Kesby runs the live Kick-Off and the Accountability sessions that keep the cohort moving. Recorded, so you never lose one.

LiveRecorded
1:1 with Anita · AI

CoWork session

Do a real task inside Claude CoWork, like board prep or an executive brief. You ship an artifact, install a Skill, and log a Value Impact receipt.

Installs a Skill
1:1 with Anita · AI

Mini upskilling

A short mentored walk-through around a mini deck, so each new habit lands before you apply it.

~10 min

The work you'll actually do.

CEO OS V3: The CEO Operating System is a stack of Claude CoWork Skills designed to amplify the time of CEO's and Executives. 12 hands-on activities, run on your own problems.

Beginner

Velocity Forum Kick Off Session — Mini deck — Part A

Mini deck
1:1 with Anita
Intermediate

Board Meeting Prep for CEOs intermediate

CoWork · +Skill
1:1 with Anita
Advanced

Board Meeting Prep for CEOs intermediate advanced

CoWork · +Skill
1:1 with Anita

Your learning journey

Your 4 weeks, step by step.

Each week sits the live sessions either side of your 1:1 activities with Anita: board prep, executive briefings, and operations risk scans on your real work.

Kick-Off · humanJourney activities · 1:1 with AnitaAccountability · human
Week01
Live session
Kick-Off Session
90 min · Matt Kesby
Mini deck
Velocity Forum Kick Off Session — Mini deck — Part A
$240/mo
CoWork · +Skill
Board Meeting Prep for CEOs beginner
$720/mo
CoWork · +Skill
Board Meeting Prep for CEOs intermediate
$720/mo
No session
Week02
No session
Mini deck
Velocity Forum Kick Off Session — Mini deck — Part B
$240/mo
CoWork · +Skill
Executive Brief Agent Fundamentals
$720/mo
CoWork · +Skill
Executive Briefing Enhancement
$720/mo
Live session
Accountability Session
45 min · Matt Kesby
Week03
No session
Mini deck
Velocity Forum Kick Off Session — Mini deck — Part C
$240/mo
CoWork · +Skill
Ops Risk Scan for CEOs
$720/mo
CoWork · +Skill
Operations Risk Management for CEOs
$720/mo
No session
Week04
No session
No session
No session
No session
Live session
Accountability Session
45 min · Matt Kesby

Weeks and activities render from the cohort's learning journey. CoWork sessions install a Skill and log Value Impact; Mini deck sessions are short mentored walk-throughs.

From leaders who stopped experimenting.

"I'd dabbled with AI for a year and changed nothing. Four weeks of real reps and board prep is now a Friday afternoon, not a lost weekend."

DR
Daniel Reyes
CEO, Manufacturing

"The cohort kept me honest. Doing the work on my own briefings, with a coach watching, is what finally made it stick."

PN
Priya Nair
Founder, Fintech

"I came in skeptical about another course. I left with a routine I still use every single day."

TH
Tom Hartley
Operations Director, Construction
Author portrait

Built by the author

Built on the work behind Untangling AI.

This program draws on the methods of Matt Kesby, author of Untangling AI (Wiley), a USA Today best-seller. The approach is the same throughout: less theory, more reps on the work that pays you back.

Untangling AIUntangling AIWiley · USA Today best-sellerNational best-seller

Enroll · kicks off Monday, June 22

One seat. A routine that *keeps paying.*

  • Live Kick-Off and Accountability sessions with Matt Kesby
  • 12 one-to-one activities with Anita
  • The full CEO OS V3 Skill stack, installed and yours to keep
  • A working Claude routine you run long after week 4
$99.00

per seat · one-time

Enroll now
closes before Monday, June 22

Only seats left in CEO Claude CoWork Upskilling - CEO OS V3 20260616 with Matt Kesby.

Lead · Practice · Compound

Stop experimenting. Start operating.

Join CEO Claude CoWork Upskilling - CEO OS V3 20260616 with Matt Kesby, do the real work with Anita, and leave with a Claude routine built into how you lead.

Program schedule