Self-Paced · Founding Member Pricing · $397

The Complete AI Playbook
for Chiefs of Staff.
On Your Schedule.

Six modules. Sixty minutes each. Frameworks, tools, and templates built specifically for CoS operators — built to implement on your timeline, not ours.

Enroll Now
6
Implementation modules
Tools & Templates Library included
10+
Hours reclaimed weekly
Lifetime access, all updates
Who This Is For

Built for the operator who moves on their own terms.

You're a Chief of Staff. You know how to prioritize. You don't need a fixed weekly session to get something done — you need the right material, the right tools, and a clear path. That's exactly what this is.

You get the same training video modules, the same templates, and the same frameworks used in the live cohort — built to implement in the windows you have, not on someone else's schedule. Step-by-step workflow guides and templates mean you're never building blind.

If you want Matt, our AI and technology strategist, in the room with you during the builds — or want a cohort of peers going through it at the same time — the live cohort is the deeper option. Both tracks get you to the same place.

This track is a great fit if...
  • You want to move at your own pace and on your own schedule
  • You prefer to absorb material before implementing — on your terms
  • You're comfortable using step-by-step blueprints and documentation
  • You want lifetime access to revisit modules as your role evolves
  • You'd like to get started now rather than wait for the next cohort
Also worth considering...
  • The 6-Week Live Cohort ($3,000) — if you want Matt in the room every week and a cohort of peers building alongside you
  • CoS AI Lab ($44/mo) — if you want ongoing live workshops, office hours, and a community to stay current as AI evolves
The Curriculum

Six modules. Each one ends with something built.

Six modules of structured walkthroughs and implementation frameworks — built specifically for the CoS role. Watch when you have time. Implement when you're ready.

These are the same training video modules used in the live cohort. Watch at your own pace. Implement on your own schedule. Everything is built inside Claude Cowork — one platform, no external tool stack required. Step-by-step workflow guides and templates mean you're never building without a map.

Module 1

Platform Mastery & Your Operating Foundation

Stop thinking like a user. Start thinking like a systems architect. You'll learn exactly how Claude Cowork works — its three modes, its tools, and how to use it the way it was designed to be used. Then you'll build your first real wins in your actual role.

  • Understand Chat, Cowork, and Code modes — and when to use each
  • Set up Artifacts, Projects, and Skills so your work compounds across sessions
  • Master the five-element prompt framework that produces principal-ready output
  • Complete your Automation Roadmap — a prioritized map of your most automatable hours
You Build: Automation Roadmap + Your First 3 Real Workflows
Module 2

Intelligence Infrastructure: Context, Projects & Prompt Mastery

Without context infrastructure, you re-explain yourself every session. This module builds the three-layer system — Global Instructions, Project Instructions, and CLAUDE.md — so Cowork already knows you, your CEO, and your org before you type a word.

  • Build Global Instructions that change the quality of every future session
  • Set up the five projects every CoS needs: Board Prep, CEO Comms, Hiring, Weekly Ops, Strategic Initiatives
  • Create stakeholder profiles for your full relationship map
  • Write prompts that work without you — the skill that makes automation possible
You Build: Full Context Stack + Board Prep Folder + Stakeholder Profile System
Module 3

Connected Tools, Research & Data Intelligence

This is where Cowork stops working with files and starts working with your entire world. Connect Gmail, Calendar, Slack, Notion, and project trackers — then run the research and cross-tool workflows that used to require four open tabs and an hour of copy-paste.

  • Connect and troubleshoot your key tools — the full MCP walkthrough
  • Run the Morning OS: Gmail + Calendar + Slack in one prompt, every morning
  • Build the CEO Context Packet — decisions made, risks emerging, what the CEO needs to know
  • Analyze real spreadsheet data and produce an executive narrative without a data analyst
You Build: Morning OS + CEO Context Packet + Data Analysis Workflow
Module 4

Meeting Operations, Executive Communications & Hiring

CoSs support 15–25 meetings a week. This module builds the full meeting lifecycle — prep, processing, follow-up — and covers every executive communications type, sourced from real data and drafted in your CEO's voice. Plus hiring and onboarding workflows.

  • Build the full meeting lifecycle: external prep brief, transcript processing, post-meeting follow-up
  • Create your CEO's voice document — the artifact that calibrates every future draft automatically
  • Source-connected communications: weekly updates, board briefs, OKR narratives — from real data, not blank pages
  • JD creation, evaluation frameworks, and 30/60/90-day onboarding plans
You Build: CEO Voice Doc + 5 Comms Templates + Meeting Intelligence Archive
Module 5

Workflow Design, Skills & Your Automation System

Everything you've built so far, converted into one-click Skills and scheduled to run without you. You wake up. Your morning briefing is in your inbox. Your CEO's context packet is ready. The meetings have prep briefs. You didn't do any of it.

  • Design workflows from scratch using the IPO framework (Inputs → Process → Outputs)
  • Convert your best workflows into Skills — saved, one-click, reusable
  • Schedule 4 core automations to run without a manual trigger
  • Board prep end-to-end: 3 hours → 30 minutes, getting faster every quarter
You Build: 5+ Custom Skills + 4 Scheduled Automations + AI Operating System
Module 6

Scale, Org Leadership & Your AI Operating System

You've built the system. Now you lead the org through it. The CoS is the right person to drive company-wide AI adoption — you have the cross-functional visibility, the executive trust, and now the technical fluency. This module shows you how.

  • Run a departmental AI audit — a prioritized opportunity matrix for every function
  • Draft your company's AI policy and resistance playbook for leadership buy-in
  • Package your personal skills for org-wide distribution
  • Produce your 90-day AI roadmap + AI Operating System doc — the course capstone
You Build: Org AI Audit + AI Policy + 90-Day Roadmap + AI Operating System Doc
The Resource Library

Everything you need to implement after you watch.

Not generic templates you could find anywhere. Built specifically for the CoS role, tested in real CoS workflows.

Tools & Templates Library

Organized by use case: communications, research, synthesis, operations, board prep. Every prompt we use in the videos, plus dozens more built for common CoS tasks.

5 Communication Templates

Pre-built and ready to customize: board updates, stakeholder memos, difficult messages, weekly digests, decision documents. Built around your exec's voice.

Workflow Guides & Skill Templates

Step-by-step guides with screenshots for every build in the program. When something needs updating six months from now, you have the map to do it yourself.

Voice Document Template

The section-by-section build guide with examples that takes you from blank page to a complete voice document in under an hour.

Role Audit + Automation Canvas

Two worksheets: the role audit that shows you your 10 most automatable hours, and the automation canvas that maps any workflow before you touch a tool.

AI Opportunity Audit Framework

The org-level analysis framework from Module 6. The guided questions for each functional area and the rating criteria that turns a conversation into a ranked proposal.

Investment

Simple, transparent pricing.

Self-Paced Course
Founding Member Pricing
$397 $497
One-time · Lifetime access · All future updates included
6 modules · 35+ workflows · 50+ templates
5 communication templates
Workflow guides & skill templates
Private community access (1 year)
Lifetime access + future updates
Enroll Now
Want accountability + live builds? Consider the 6-week cohort ($3,000) or CoS AI Lab ($44/mo) instead.
Before You Go

Questions worth answering honestly.


What if I've tried AI courses and not finished them?

That's a real data point about yourself — not a character flaw. The self-paced format works best for people who finish things on their own. If that's not reliably you, the cohort structure is specifically designed for that problem. We'd rather lose the sale than have you buy something that doesn't work for you.

Is the content different from the cohort?

The frameworks, tools, and templates are the same. What's different is the implementation context: no live developer, no cohort accountability, no real-time unblocking. Same map, different guide.

Will this get outdated?

Yes — and that's why lifetime access includes all future updates. When we add new modules, update templates for new tools, or swap out tools that have gotten better alternatives, you get it. No rebuy, no upgrade fee.

Do I need any technical background?

No. The modules are designed for operators, not developers — the whole point is that you don't need to understand how it works under the hood, just how to configure and maintain it.

Can I upgrade to the cohort later?

Yes. If you enroll in the self-paced course and decide you want the live cohort experience, we'll credit your $397 toward the $3,000 cohort price. You'll never feel penalized for starting here.

Ready When You Are

The operators who are indispensable in two years are building their systems today.

Every week without these systems is a week of Sunday night rewrites, manual compilation, and your best hours going to work that should be automatic.

Enroll Now

Lifetime access · All future updates included · Upgrade credit toward cohort available