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I ran a live Agentic CEO workshop and walked a room of founders through turning Claude into an AI Chief of Staff: a system that runs the inbox, drafts the follow-ups, and remembers the business. The step-by-step build lives inside Gen AI University. This is the map, not the manual.
Watch the full workshop: The Agentic CEO Workshop on YouTube
Most founders don't have a time problem. They have a "carrying the whole business in their head" problem. Every unsent follow-up. Every partner you meant to check in with. Every plate spinning that you're personally responsible for keeping in the air. Drop one and you usually don't notice until it crashes.
The standard fix is "hire an executive assistant." Good advice. The catch is that most operators never do it, so they stay their own assistant. They run the calendar, triage the inbox, chase the leads, and write the recap emails themselves, on top of the work only they can do.
In this workshop I showed founders a different way to close that gap: hire an AI Chief of Staff instead. Not a chatbot you re-explain yourself to every morning. A system that knows your business, runs the repetitive work, follows up, and remembers everything, with Claude as the backbone.
I have been building and running my own version of this for years. I was one of Jasper's first customers back in 2021, and today a setup like this runs the connective tissue across three businesses. So none of what follows is theory. It is the system I use every day, generalized so you can build your own. Mine is named RIFF, because you riff back and forth with it.
And to be clear: this is a build for operators, not engineers. Everyone in that room runs a business, not a codebase. If you can describe how you work, you can build this.
Being an Agentic CEO is simple to say and harder to live: you stop doing the repetitive work and start commanding a team that does it for you. The goal isn't to serve your AI. It's to get your AI serving the highest and best use of your time, and to offload the small hinges, the tasks that quietly open or close bigger doors.
1. Claude on your desktop. This lives in Claude's desktop app, not the browser tab most people start in. The desktop app unlocks two surfaces: Cowork, the approachable one, and Claude Code, the deeper one, a single tab over. You do not need to become a programmer to use either.
2. Connectors: your existing tools, wired in. This is the piece that turns a smart assistant into a useful one. Through connectors, Claude can reach the tools you already run your business on: Gmail, Calendar, Google Drive, Slack, Notion, Webflow, your meeting notes, your CRM. Nothing new to learn. It works where you already work.
3. Skills: specialized agents for specific jobs. A skill is a trained operator for one kind of task. Triage the inbox. Draft outreach. Research a market. Build a newsletter. You assemble the ones you need, and your Chief of Staff routes each request to the right one.
4. Scheduled tasks: the work that runs without you. This is where it stops being a tool and starts being staff. A daily inbox briefing. A weekly check-in drafted for a key partner. A monthly newsletter researched and written for your review. You set it once. It runs.
5. Dispatch: your Chief of Staff in your pocket. Sync the Claude app to your phone and you can hand off work from anywhere. An idea at your kid's volleyball game. A follow-up you don't want to forget at dinner. Send it, and it's handled by the time you're back at your desk.
The piece that makes the whole thing compound is memory. Out of the box, Claude is brilliant and amnesiac. It starts every conversation at zero. The fix is a persistent memory layer, a second brain that gets updated as you work. Many founders in the room are building theirs in Obsidian, a free desktop app, so their assistant keeps a living record of clients, projects, decisions, and priorities. RIFF does exactly that for me.
Yours can be named anything. What matters is that it remembers.
A tool you re-explain every morning. A teammate that already knows. The difference is memory.
A few principles came up again and again:
The use cases that surfaced live, from the people in the room:
None of these require a bigger team. They require a system. One subscription now does work I used to scope out piece by piece, and unlike a pile of one-off tasks handed around, a system compounds. Every correction you make teaches it. It gets sharper while you sleep.
The plate you dropped last week. The partner who went quiet because you never circled back. That is the real cost of being your own assistant, and it is the first thing worth handing off.
That is the question that started this whole build. Most of us are bad at asking for help even when we need it. So flip it: if support simply showed up for you tomorrow, what would it take off your plate?
Answer that with specifics and you have the blueprint for your first skill. For most founders the answer is the inbox, so start there: a daily briefing that reads what came in overnight and drafts the replies you would have written anyway. One brick. Then the next.
That is the Agentic CEO path, and it is where Gen AI University founders are spending their time. Not studying AI. Building agentic companies with it. Brick by brick.
What is an AI Chief of Staff? A system built on Claude that knows your business and runs the repetitive work: triaging your inbox, drafting follow-ups, scheduling recurring tasks, and remembering your projects, clients, and decisions, so you stop being your own assistant.
Do I need to know how to code to build one? No. This is a build for operators, not engineers. If you can describe how you work and what a good outcome looks like, you can build one. The workshop series inside Gen AI University walks you through it step by step.
Where do I start? With the one thing you would hand off first. For most founders that is the inbox: a daily briefing that reads what came in overnight and drafts the replies you would have written anyway. Build that one brick, then add the next.
The Agentic CEO Workshop: Building Your AI Chief of Staff
Want to build your own? The community is free to join, and I run this as a live, recurring series. Inside Gen AI University you get the full system, the workshop recordings, and the step-by-step build I won't put in a public post. Start free at genaiu.com, then come build your Chief of Staff with us. Brick by brick.
P.S. If you do one thing this week, point your AI at your inbox tomorrow morning. Let it read what came in overnight and draft the replies. That is the first brick.
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