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.
Quick answers about the AI-Powered Executive lane.
What is the AI-Powered Executive Session?
It is a 90-minute working session where Mark helps an individual executive build one practical AI Chief of Staff workflow around how they already run their week.
Who should book the executive session?
It is for executives, founders, fractional leaders and senior professionals who want AI to help with their own operating rhythm, not the whole company's AI strategy.
What do you leave with?
You leave with one working AI-assisted workflow, shaped around your preferences, recurring work and the way you make decisions.
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.
01
Start free
The AI Chief of Staff starter kit. One paste and thirty to forty-five minutes gets you a working starter, the same starting point everyone gets, that you set up and shape yourself. Yours to keep, no charge.
02
Book a session
Ninety minutes together. I learn how you actually run your week and turn it into the rules and routines your chief of staff runs on. Yours, not the generic build. Running before we hang up. $500.
03
Join the program
The AI-Powered Executive. AI moves faster than anyone running a company can track. Each month: my read on what changed and what to do about it, a new piece for your system, a live session with me, and a small room of executives building the same way.
04
Go deeper
Once it is running for you, the next question is usually your team. Wiring this into how the company works, or building an AI plan for the organization, is my fractional Chief AI Officer work.
The AI-Powered Executive Session
Built around how you actually work.
The free kit gives everyone the same starting point. This is ninety minutes building
yours: fitted to your week, and dependable enough that you hand real work to it. $500.
Before we meet, you tell me how your week actually runs: when you protect your time,
what you want handled without being asked, how you like to be briefed. Then we build
it together on your real accounts, and it is running before we hang up.
In practice, the things you already know about yourself become rules it follows:
"I protect my mornings, so nothing gets booked before ten."
"Draft my replies, but never send anything without me."
"Before anything else, tell me who I owe a reply to."
Any AI will follow a rule like these once, then a new chat starts and it forgets.
Making them hold every morning, without you checking, is the difference between a
tool and a system.
01
Your own AI Chief of Staff
Not the generic starter. One shaped around your role, your preferences and the way your week actually runs, built with you and running before we hang up.
02
A standing morning brief
The routine scheduled and running, so it briefs you the next morning without being asked. Not a tool you have to remember to open.
03
A thinking partner that keeps up
Correct it once and it remembers. As your week changes, it changes with you, which is why it is worth more in month three than it is on day one.
This is mine, over a year in and several rebuilds later. It gives me back at least
eight hours a week, and that is only counting what is on this screen. Every panel
here started the same way: it handled one thing reliably, so I gave it the next.
Book your AI-Powered Executive Session.
Ninety minutes on Zoom, with a 30-day money-back guarantee. If it is not worth what
you paid, tell me and I will refund it.
The rate goes to $800 once I have a set of completed case studies. You are early, so
it is $500.
I am Mark Bennett. I co-founded Sentry Enterprises and ran it as CEO for eight years,
where I led the integration of AI across the engineering organization. Before that I
spent thirteen years at CME Group, where I led a 250-person software engineering
organization. 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. This site, its backend and the email system behind it
took me about two days. I have built multiple AI platforms, billing and admin tooling
included, and several are in production use right now. I run my week on one of those
systems. When I say a thing is buildable this week, I am not estimating.
Questions people ask
Before you book.
The free kit builds a chief of staff too. Why pay for the session?
The kit is the real thing, not a teaser, and it connects to your calendar and inbox too. It builds from a generic template and whatever you think to tell it. Describing how you work is the easy half. The hard half is turning that description into behavior the system repeats reliably, which takes knowing where these tools hold and where they quietly drift. In the session I do the translating: you describe how your week actually runs, and I turn that into the rules and routines the system runs on. 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?
Claude. It needs a paid Claude plan with Cowork, which is what lets it work with real files, connect to your calendar and inbox, and run on a schedule. Plans start at $20 a month. You will also need a Google or Microsoft account. The free kit has the same requirements, and I tell you exactly what to turn on.
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 and the program both carry a 30-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.
Live workshops
Learn it in a room.
I run live workshops on becoming an AI-powered executive. Seats are limited. 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.
The dashboard above did not start out looking like that. It got there one piece at a
time, and that is what the AI-Powered Executive program is for.
A written read each month on what actually changed in AI and what decisions it should affect.
A new tool or upgrade to install, every month.
A live call where I take the members through a few things worth your attention, then answer whatever you bring.
My inbox, between calls. Email me with whatever comes up. I answer.
The tools will keep moving whether or not you have time to follow them. This is how you
stay in front of that without making it your second job.
I am opening it to a first group of fifteen founding members. You 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. 30-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 and it does not commit you. I reply
personally, you get a straight answer on whether it is worth your money, and if it is
not I will tell you. Privacy policy.
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 yours built with you, on your real work, book a session.
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