Beginner
Velocity Forum Kick Off Session — Mini deck — Part A
Mini deck
1:1 with Anita
Live cohort · 4 weeks · Kicks off Starting soon
Build daily Claude CoWork habits into how you lead.
A guided 4-week cohort for senior leaders. Live sessions with Matt Kesby, plus 1:1 journey sessions with Anita, your AI facilitator. You practice on your own work, not toy examples.
● 13 languages● Matt 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
Your forecast Value Impact · 12 months
What this routine gives back.
As you complete activities, the cohort tracks the Value Impact you log against your real work.
People using the Skills12
Blended hourly cost$120
Skills installed
9
permanent
Hours saved · per year
8,640Across your team, every week, all year.
Value created · per year
$1.0MHours back, converted to cost saved.
Return on the cohort
218×Against $397.00.
Calculated from the 12 journey activities in this cohort: about 60 saved hours per person each month, from conservative per-activity rates. Most teams beat it.
Why traditional training fails
Most executives never get past the experiment.
You have opened Claude. Maybe asked it a few things. Then the week swallowed you and the tab went stale. The problem is not the tool. It is the lack of a routine.
- •AI stays an occasional novelty instead of part of how you run your week.
- •Board prep, briefings, and risk reviews still eat the hours they always did.
- •You delegate the thinking that should compound into your own judgment.
- •No one shows you how to do this on your real work, at your level.
Habits, not hype.
This cohort installs a working routine you keep using long after the 4 weeks are done.
Knowledge retention over time
Weekly Value Impact
Anonymised average · Recent cohort
Value Impact
Every session leaves you with *something you keep.*
You do real work in each activity, then log what it returned. Proof you can point to, not a feeling.
- ✓A board meeting prep workflow you run again next quarter.
- ✓An executive briefing routine that tightens your reporting.
- ✓An operations risk scan you can repeat across the business.
- ✓Installed Skills that stay in your workspace after the cohort ends.
What you walk out able to do.
Board prep
Walk in ready
Prepare for board meetings with Claude drafting, structuring, and pressure-testing alongside you.
Briefings
Sharper reporting
Build executive briefings that say more in less, on a repeatable workflow.
Risk
See it sooner
Run an operations risk scan that surfaces what you would have missed.
Routine
A daily habit
Leave with Claude woven into how you actually run your week, not a forgotten tab.
Made for the people who actually decide.
This cohort is shaped for experienced leaders and the work that lands on their desk.
Industries
B2B (general)Boutique HotelsConstructionElectrical EngineeringFintechHealthcareManufacturingPayment FacilitatorProfessional servicesReal estateSaaSWealth managementEnergyFinanceAccounting & BookkeepingCivil EngineeringCommercial ConstructionCommercial Real EstateFinancial PlanningInsuranceLegal ServicesMarketing & Creative AgenciesProperty ManagementRecruitment & StaffingResidential BuildingStrata & Body CorporateTrades & Home ServicesTechnologyManagementCorporateConsultingmanagement consultingEnterprise
Roles
ExecutiveCEOFounderOperationsSalesAccount ExecutiveAccount Executive (AE)Sales Development Rep (SDR)MarketingAccountsBdrBuyerConciergeEstimatorExecutive OfficerLeasing AgentProcurementProperty ManagementProperty ManagerPurchasingRev OpsSales ManagerTrust Accountant
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 reps 1:1 with Anita on your own work.
Human-led
Kick-Off & Accountability
Matt Kesby runs the live Kick-Off in week 1, then Accountability sessions keep the cohort moving. Every session is recorded, so you never lose one.
LiveRecorded
1:1 with Anita · AI
CoWork session
Do a real task inside Claude CoWork, like prepping a board meeting or scanning for ops risk. 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, built across the Kick-Off in three parts.
~10 min
The work you will actually do.
Twelve hands-on activities across the CEO OS V3 journey, each on your own real work.
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, week by week.
Each week sits the live human sessions either side of your 1:1 activities with Anita.
| Kick-Off · human | Journey activities · 1:1 with Anita | Accountability · human | |||
|---|---|---|---|---|---|
| Week01 | ◉ Live session Kick-Off Session | 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 |
| 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 |
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.
Your team
Your coach, and Anita.
Human coach
MK
Matt Kesby
Lead facilitator · live sessions
AI facilitator
AI
Anita
1:1 journey sessions · 13 languages
Anita is your AI facilitator. She runs your 1:1 activities between live sessions, so you get the reps when it suits you.
Bring your real work.
This only works because you practice on what is actually on your plate.
A real decision or document
You bringAn upcoming board pack, a briefing you owe, an operations question you keep circling. Bring it in.
A focused slot each week
Your timeOne live session plus a couple of short 1:1 activities with Anita. Most weeks land around 30 to 45 minutes.
Untangling AIWiley · USA Today best-sellerNational best-seller
Built by the author
Who built this.
This program is built on the work of Matt Kesby, author of Untangling AI (Wiley), a USA Today best-seller. The approach is simple: stop treating AI as a novelty and put it to work on the things you already do, until it becomes a habit you keep.
Matt KesbyAuthorWhat leaders say after four weeks.
"I came in skeptical that this would survive contact with my calendar. The board prep workflow alone changed how I run that week."
DR
Daniel Reyes
CEO, Manufacturing
"The difference was doing it on my own briefings, with a coach watching. It stuck because it was real work, not a demo."
PN
Priya Nandakumar
Founder, Fintech
"The ops risk scan caught things I had a nagging feeling about but never made time to check. Now it is a routine."
HV
Helena Voss
COO, Boutique Hotels
Enroll · kicks off Starting soon
One seat. A *year of compounding.*
- ✓Live Kick-Off and Accountability sessions with Matt Kesby
- ✓12 one-to-one activities with Anita across the CEO OS V3 journey
- ✓Installed Claude CoWork Skills you keep, forever
- ✓Session recordings you can rewatch any time
- ✓A working routine you keep using after the 4 weeks
$397.00
per seat · one-time
Enroll nowcloses before Starting soon
Live sessions are recorded, and videos are available to watch back any time. seats left for CEO Claude CoWork Upskilling - CEO OS V3 20260618 with Matt Kesby.
Questions
Before you enroll.
One live session plus a couple of short 1:1 activities with Anita. Most weeks land around 30 to 45 minutes.
No. This is built for senior leaders, not engineers. You bring the work, Claude and Anita handle the mechanics.
Every session is recorded and the videos are available to watch back whenever it suits you.
Yes. You keep the installed Skills, the artifacts you produce, the recordings, and the working routine you build.
No. You practice on your own real work in every activity, from board prep to briefings to operations risk.
Upskill · Accelerate · Outpace
Your next move starts here.
Join CEO Claude CoWork Upskilling - CEO OS V3 20260618 with Matt Kesby, do the real work with Anita, and walk out with a Claude routine you keep using all year.