You lose things through the cracks and find out later.
Every decision, every follow-up, every thread runs through you. You are the only one holding the whole picture, so nothing moves while you are heads down, and what you drop is not picked up.
The AI-Powered Executive
Become an executive who runs on AI.
A monthly program for executives who want more of their week running without them. A clever prompt changes an afternoon. A system changes every week after it.
I'm Mark Bennett, a former eight-year CEO of a deep technology company and head of international technology operations for CME Group. I built these capabilities because I desperately needed them as a founder and executive. This program puts those same tools in your hands.
Why executives come to this
You have the tools. I help you build the system.
You do the work you hate because there is nobody else.
Hiring is the obvious answer and it is not open to you. The salary is real money, the search takes months, and you would still have to explain how you work to whoever you hired. So it gets done at the end of a day already spent.
You are too busy delivering to find the next client.
The client work that pays for this month has a deadline. The work that fills the pipeline for next quarter does not, so it takes a back seat. A few months later, you feel the gap.
See how much still lands on you, and how far your own AI use has already taken you.
What you get
What you get every month.
01
Your own AI Chief of Staff
Built with you in your build session. It reads your calendar and inbox, and you teach it the rest: your people, your projects and what you promised whom, so nothing you write starts from a blank page.
02
A new capability every month
Each month you add another piece that takes on more of your week. Recent additions have connected Slack and LinkedIn context, checked drafts against their sources and helped writing sound like the person behind it.
03
Live sessions with me
Join scheduled sessions where I share the latest tips and insights, then open the floor. Bring a problem, a decision or simply listen. You choose the sessions that fit your schedule.
04
The monthly brief, and member library
A concise read on what changed in AI and why it matters to your work. Alongside it, the member library gives you practical tools, prompts, techniques and masterclasses.
Who's building this with you
I have sat in the chair you are sitting in.
I had teams around me and still ended most weeks with a list only I could clear. Over a year ago I built the AI-powered system I now use every day. It has grown every month since, and it now carries what I would otherwise be holding in my head. Everything I share with you is something I use.
The book
The Chief of Staff You Can’t Afford to Hire
Coming to Amazon Kindle and print soon.
Members get the digital and printed editions free.
Free workshop
Becoming an AI-Powered Executive.
In one session I show you how to build the basics of your own AI Chief of Staff, and how the monthly program works if you want to keep going.
First and third Thursday of every month, 1 pm and 7 pm Eastern, about an hour.
Leave your details and I will save you a seat at the next one, and send you the AI chief of staff kit so you can start building today. The recording goes to everyone who attends.
Membership is $99 a month if you decide to join. The workshop is free and there is nothing to buy to attend.
No commitment. Privacy policy.
The shift
The same AI. A different operating model.
There are two ways to use AI. Most people prompt it. Few run their week on it.
Prompting
- Open a blank chat
- Describe the people and project again
- Add the relevant facts and past decisions
- Explain what you need
- Receive an answer for this task
Next task: start over
Running on AI
Live inputs
- Calendar
- Inbox
- Explain what you need
Memory
What the system already knows
- People
- Projects
- Facts
- Decisions
The system applies what it knows
It responds to each task with your people, projects, facts and decisions already in view.
- Morning brief
- Meeting prep
- Follow-through
What it covers
More of this is judgment than building.
Installing tools is the visible part and it is the smaller part. Most of what separates an executive who runs on AI from one who owns a subscription is knowing what to reach for, what to ignore and what to hand over.
Keeping the memory true
A system that quietly goes stale is worse than none. Yours should check its own memory and flag conflicting or outdated facts before you act on them.
What to hand over first
Writing down the week exposes the drafting, chasing, summarizing and repeated explanation that do not need you. Those are usually the first jobs to move.
The prompts and patterns I use
Meeting prep, document review, decision memos and hard emails that still sound like you. You get the patterns I actually run, not generic prompt lists.
Working with it, not just building it
Calendar and inbox access is only the start. The lasting skill is knowing what to tell the system, when to correct it and which work to keep for yourself.
Questions people ask
Before you join.
How do I know this works?
Mine has run every day since June 2025. It did not arrive all at once, it came together a piece at a time, and every piece began as something I needed that week. It is not perfect. Early on it kept being confidently wrong about what day it was, so I built it a clock it cannot argue with. A lot of what is in there now started exactly that way.
How much of my time does this take?
Sixty to ninety minutes for your build session. After that, an hour or two a month covers the session, installing updates and reading the brief. Spend more if you want to move faster.
Do I need to be technical?
No, and you will not be doing it on your own. Your build session is a live walk through with me and a handful of other new members, where we configure yours around the work you actually do and I troubleshoot whatever goes wrong while you are doing it. It is small enough that I can stop for you. If you already have the basics running, we take yours further instead. You will not write code. You will need a paid Claude or ChatGPT plan, which start at $20 a month. Build sessions run every couple of weeks, so if something does not go in cleanly you can sit in on the next one.
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. In a session you are working in your own accounts on your own screen, and nobody else in the room sees your calendar or your inbox.
What if it does not work for me?
The program carries a 30-day money-back guarantee, and you can cancel any time. If it is not for you, you are not stuck.
See how the system works before you decide.
The workshop is free. I show you how to build the basics and how the monthly program works.