Build Your AI Chief of Staff
Benjamin Jackson
AI builder & executive coach
Stop losing track of what matters
It’s Thursday, and you realize you promised to send your boss something after a meeting on Tuesday… and you have no idea what it was. It’s Friday night, and your partner says “did you ever make that reservation?” (You did not.)
The big things get done. But the small stuff slips. And the cost isn’t just the dropped ball. It’s the trust you’re quietly burning every time another thing falls through.
You’ve tried apps. You’ve tried willpower. But the problem isn’t you. Getting things into any system takes more steps than the moment allows. And finding them means searching in tools you stopped using weeks ago.
In this course, you’ll use Claude Cowork to give AI access to your projects, email, calendar, and open tasks. You decide what it sees: Claude reads the folder you point it to, nothing else. It can draft emails, but can’t send or delete them.
If you’ve ever talked to Claude, you’re ready. The hardest part is setting up. After that, there’s no code, no prompts; just check your daily briefing. (Video ↗)
The first session is a step-by-step walkthrough, no prior setup. And you’ll be in a group of smart people who’ve never done this before.
Still unsure if you’re ready? Ask Claude ↗
What you’ll learn
Claude Cowork is a secure, easy way to use Claude on local files. You’ll learn how to use it to manage your email, schedule, and open tasks.
Connect your email, calendar, and meeting notes to Claude in minutes.
Learn what Claude can and can’t see, so you trust it before you start using it.
Grab todos and follow-ups with Siri, shortcuts, or a quick note.
Everything lands in your system automatically. Nothing stays in your head.
Set weekly, monthly, and quarterly priorities through conversation.
Walk into Monday with your top three outcomes already clear.
Get a summary before each meeting with context on where things stand.
Know who you're meeting, what you discussed last time, and what's on the agenda.
Get a one-on-one with Ben to customize your system to your workflow.
Connect to the tools you already use: Asana, Notion, Slack, you name it.
Learn directly from Benjamin
Benjamin Jackson
Wharton visiting expert, teaching executives to build with AI
Who this course is for
Busy executives: You manage multiple projects and stakeholders. The big stuff gets done, but follow-ups and small tasks still slip through.
Curious leaders: You know AI is changing work, but you’re still looking for a way in that doesn’t feel like it was built for startup bros.
Productivity junkies: You’ve tried Todoist, Notion, Asana, and a dozen others. They all worked for a month, then started collecting dust.
Prerequisites
You’ve used ChatGPT, Claude, or another AI app
No need to be an expert. If you've had a conversation with an AI, you're ready.
You can install the Claude desktop app (Mac or Windows)
Download it for free at claude.com/download.
You have a paid Claude Pro account
The course uses Claude Cowork, which requires Claude Pro ($20/mo).
What's included
Live sessions
Learn directly from Benjamin Jackson in a real-time, interactive format.
Group build sessions twice a week
Bring questions, get unstuck, and steal each other’s best ideas.
Direct access to Ben throughout the course
Message Ben anytime with questions specific to your workflow and setup.
A dedicated one-on-one with Ben in week 5
Get personalized guidance on customizing your system to exactly how you work.
A library of ready-made templates you can customize
Skip to building with templates and scripts built by Ben.
Lifetime access to all course content and recordings
Go back to lessons whenever you need to.
Certificate of completion
Share your new skills and signal your commitment to learning AI skills.
Maven Guarantee
This course is backed by the Maven Guarantee. Students are eligible for a full refund through the second week of the course.
Course syllabus
14 live sessions • 23 lessons
Week 1
Apr
21
Hello, and welcome!
Apr
22
Live build session: Connect the essentials
Lessons: Get set up and connected
Apr
22
Office Hours 🌛
Apr
24
Office Hours 🌞
Week 2
Apr
29
Live build session: Create your unified inbox
Lessons: Capture anything in seconds
Apr
29
Office Hours 🌛
May
1
Office Hours 🌞
Schedule
Live sessions
1-2 hrs / week
We’ll set up Claude Cowork, build our systems together, trade notes, and troubleshoot any issues.
Tue, Apr 21
10:30 PM—11:00 PM (UTC)
Wed, Apr 22
4:00 PM—5:00 PM (UTC)
Wed, Apr 22
10:30 PM—11:00 PM (UTC)
Projects
1-3 hrs / week
Between sessions, you’ll keep using (and tweaking) your system to fit your needs.
Reading (Optional)
1 hr / week
There’s optional reading, but most of your time will be spent building and testing your system.
Testimonials
None of this requires a technical background. I’m reading white papers on AI and the impacts on human intelligence in the future, and this class unblocked me by helping me break my fear of really learning AI.
Kim Patel
Startup Banking, Midwest @ J.P. Morgan
What your Monday morning could look like:
Frequently asked questions
$799
USD