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Start free
The AI Chief of Staff starter kit. One paste stands up a working chief of staff in about fifteen minutes. Yours to keep, no charge.
The AI-Powered Executive
Become an executive who runs on AI.
It starts with your own AI Chief of Staff: a working system that knows your people, reads your calendar and inbox, briefs you every morning and carries the follow-through you keep dropping. In ninety minutes we build yours together, wired to your real accounts and your real work.
If this sounds familiar
You have the tools. You do not have the system.
- You have ChatGPT or Claude open all day, and it still behaves like a smarter search box.
- You have read the AI think pieces. You still could not name the three things in your week AI should own.
- Your calendar, inbox and follow-ups live in your head, and things fall through.
- You have had enough theory. You want the thing running in your business by Friday.
If you recognized yourself in two of these, you are who I built this for.
The shift
The shift most executives have not made yet.
There are two ways to use AI. Most people prompt it. A few run on it.
Prompting is asking a blank chat window a question and getting an answer back.
Running on it means the AI already holds your context, so it knows the board meeting is Thursday, who sits in the room and what you promised them last time.
Closing that gap takes more than a better prompt. It takes a system that remembers your world and runs a few standing routines for you, plus the judgment to know what to hand it and what to keep in your own hands.
I run my own week on it. I built the system for my own practice first. That is what I help you build.
How it works
How you get there.
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Book a session
Ninety minutes together. We map where AI pays off in your role, then build your own AI Chief of Staff, wired to your real calendar, inbox and people. $500.
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Join the program
The AI-Powered Executive. Every month a new working install, a live working session, a decision brief on what deserves your attention and a small room of executives building the same way.
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Go deeper
When you want the whole system wired into your business, or an AI plan for the organization, that is the build. We scope it when you are ready.
The AI-Powered Executive Session
The fastest way to see what this does for you.
Ninety minutes. One ranked map. Your own AI Chief of Staff, running. $500. Most executives do not have an AI problem. They have a "where do I even start" problem. This session ends that.
Before we meet, you tell me how your week actually goes. In our ninety minutes we do two things. First, we map where AI pays off in your role and rank it, so you leave knowing your three highest-value moves instead of thirty maybes. Second, we build your AI Chief of Staff on your real accounts, so it knows your people, reads your calendar and inbox and briefs you each morning. The map then tells you exactly what to hand it next.
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A ranked opportunity map
Where AI pays off in your role, ordered by value, so you leave knowing exactly where to start.
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Your own AI Chief of Staff
Not the generic starter. One wired to your real calendar, inbox and the people you actually work with, built with you and running before we hang up.
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The recording and files
Everything we build, yours to keep, so it keeps working after we hang up.
Book your AI-Powered Executive Session.
Ninety minutes on Zoom, $500 at booking. If you do not leave with something you can use, the session is free.
Who's building this with you
I have sat in the chair you are sitting in.
I am Mark Bennett. I was CTO at Sentry and led a 250-person software engineering organization at the Chicago Mercantile Exchange. Today I work as a fractional Chief AI Officer, and I build AI systems with the same tools I put in your hands.
That last part is the difference. Most people advising executives on AI have never shipped it. I advise and I build. The site you are reading this on, the scorecard, the signup backend and the email sequence behind it, I built myself in about two days with the same methods I teach. When I tell you a thing is buildable this week, it is because I just built one.
Live workshops
Learn it in a room.
I run live workshops on becoming an AI-powered executive. Seats are limited and they fill from private rooms first. Add your name and I will tell you when the next public one opens.
One email when the next public workshop opens. Never shared, never sold. Privacy policy.
Founding cohort
Be one of the first fifteen.
I am opening the AI-Powered Executive program to a first group of fifteen founding members. Founding members get the lowest rate the program will ever carry, locked for as long as you stay, and a direct hand in what gets built. In exchange I ask for your honest feedback and a little patience with a young program.
$100 a month. Cancel anytime. Thirty-day money-back guarantee. When the fifteen seats are gone, the rate goes up for everyone after you.
This asks for a seat, it does not charge you. I reply personally and we decide together whether it fits. Privacy policy.
Questions people ask
Before you book.
The free kit builds a chief of staff too. Why pay for the session?
The kit gives you the starter version, built by you from a prompt, using whatever you tell it about yourself. In the session we build yours together on your real accounts, so it knows your actual people, calendar and inbox and fits how you really work. You also leave with the ranked map of where AI pays off in your role, which the kit cannot give you. Take the kit first. If it does what you need, keep it and save your money.
Do I need to be technical?
No. If you can hold a conversation and copy and paste, you can run this. The point is to put the technical work on the AI, not on you.
Which AI do I need?
The system runs on Claude or ChatGPT with a paid plan. I tell you exactly what to turn on. The free kit works with what you already have.
Is my data safe?
You stay in control of your own accounts. The system reads your calendar and inbox and drafts on your behalf. It never sends, books or spends without you.
What if it does not work for me?
The session carries a satisfaction guarantee and the program has a thirty-day money-back guarantee. If it is not for you, you are not stuck.
How is this different from an AI course?
A course teaches you and leaves. This installs a working system in your business and stays with you as the tools keep changing.
Start where it is easiest.
The cheapest way in is free. Take the kit and stand up your own chief of staff this afternoon. When you want the map and a tool built on your real work, book a session.