Our story
Chicago-built, self-taught
Meet Dexter Brocks, the Chicago AI Guy.
Founder and CEO of Charming AI Consulting. A decade in tech, a self-taught climb from the support desk to cloud engineer, and one conviction worth building a company on: AI is a tool, and your team can learn to use it well.
The story so far
bottom rung to here
A decade in tech, self-taught the whole way. I came up from a ground-floor support desk to cloud engineer, then walked into the AI space and did not leave. I started AutomateChicago.com building automations for real businesses, and it worked: hours came back, costs dropped, sales climbed.
Then I noticed the thing that started this company. People were not using AI wrong because they were slow. They were using it wrong because someone sold them hype instead of a tool. AI is a tool. A wrench, a hammer, an impact gun. I spent years at a Firestone learning that a wall of tools does nothing for you until someone shows you how to use them.
I am an educator first. I love handing people the keys and watching them run. It started with productivity fixes for friends, then chambers of commerce and business groups, then rooms full of people who left knowing exactly what to do next. That is what fills my cup.
Charming AI Consulting is where all of that lives. Chicago born and raised, and glad to travel wherever your team is.
The trade
what I bring to the table
What I actually do.
One brand, one honest set of tools. Everything below is work I do, not a menu of things I could someday learn.
- AI training & bootcamps
- Role-based workshops
- Keynotes & corporate talks
- Workflow automation
- Custom AI agents
- Fractional AI leadership
- AEO & AI search
- Team enablement
On the record
stamped, not spun
Who is signing the work.
The founder
- Name
- Dexter Brocks
- Title
- Founder & CEO
- Known as
- The Chicago AI Guy
- Also runs
- AutomateChicago.com
- Came up as
- Support desk to cloud engineer
- Home base
- Chicago, traveling to your team
The receipts
numbers, not adjectives
What the work has been worth.
A decade of building automations for real businesses adds up. The published engagements hang on the results wall; here is the shape of the decade behind them.
$30,000
Saved for one business with a set of simple automations.
1,700 hours
Human hours handed back to teams that stopped doing the work by hand.
85%+
Cut from a team’s manual admin workload with automated workflows.
120%
Month-over-month sales lift after the busywork got automated away.
AI is a tool like any other. A wall of tools does nothing for you until someone shows you how to use them. The charm is in the results.
On stage
this is what fills the cup
Talks that leave a room knowing what to do.
Next on stage
University of Chicago · Polsky Center
Tech Enablement Series: Using AI to Optimize How Your Business Runs
Polsky Exchange North, Chicago · July 23, 2026
The set list
AI Is a Tool. Here’s How to Actually Use It.
The Useless Bag of Goods: Cutting Through AI Hype
Automate the Boring Half of Your Business
Using AI to Optimize How Your Business Runs
AI for Leadership: What to Do Next
Empower Your Team, Don’t Replace It
Booking a talk? Say hello and tell us about the room.
FAQ
asked at the counter
Asked often. Answered straight.
Who is the Chicago AI Guy?
That is Dexter Brocks, founder and CEO of Charming AI Consulting. Chicago AI Guy is the name he speaks and teaches under. Charming is the company that houses the training, workshops, bootcamps, automation, and advisory.
Where is Charming AI Consulting based?
Chicago, born and raised. We work with teams across the city and travel to wherever yours is.
What makes your approach different?
We treat AI as a tool, not a magic trick. No hype, no headcount-reduction pitch. We train your people to use it well and build automations that pay for themselves.
Can Dexter speak at our event?
Yes. Dexter keynotes and runs corporate talks and workshops. Tell us the room and the audience, and we will shape a talk that fits. Say hello to start.