1-on-1 AI coaching · Chicago
AI Coaching for Executives in Chicago
I'm Pete Enestrom (Zaigo Coaching), and I coach executives in Chicago 1-on-1 on using AI in their own work. Sessions are in person at your office in Chicago (I travel to you) or remote, from $1,000 for a 2-hour session, starting with a complimentary 30-minute intro call. Downtown or out in the suburbs, the session runs on the forecast, the board deck and the inbox you actually have.
1-on-1 with Pete Enestrom, on your actual work
Written by Pete Enestrom
Yale & Columbia, ex-Microsoft & Intel · 1-on-1 AI coaching for executives
Your coach’s background
AI coaching in Chicago at a glance
- Format
- 1-on-1 with Pete Enestrom, hands-on, on your own work.
- Price
- $1,000 for the 2-hour Deep Dive. $3,500 for the half-day Intensive.
- Where
- In person at your office in Chicago or the suburbs (I travel to you), or remote anywhere in the US.
- Tools covered
- Claude, ChatGPT, Gemini, Perplexity, Cursor and custom AI workflows, picked for your work.
- First step
- A complimentary 30-minute intro call, where we also set the session date.
- Compare options
- How 1-on-1 coaching compares with courses and programs
How do in-person AI sessions in Chicago work?
I'm based in Greenwich, Connecticut, and I travel to Chicago for in-person sessions. Downtown that means the Loop, River North and the West Loop; outside the city, the North Shore suburbs and the corporate corridors around Oak Brook and Schaumburg.
The intro call settles the date and what we'll work on, so the session starts on substance. I come to your office and we spend the time on your own material: the forecast, the board deck, the report from the plant or the inbox that runs your day.
Remote works the same way, over video with a shared screen, if a visit is hard to schedule or you want to start right away.
What do Chicago executives work on with AI?
Chicago is a business city with a wide base: trading and financial services, the rail, trucking and air freight that make it a national logistics hub, manufacturing across the Midwest, food and consumer products, professional services firms, and corporate headquarters both downtown and in the suburbs. Executives in these industries spend their weeks on operations reviews, supplier and customer relationships, and reporting up and down. Sessions start there.
- Operations reviews: turning a stack of plant, branch or route reports into a short summary of what changed and what needs a decision.
- Supplier and customer letters: price changes, delays and renegotiations written clearly and quickly.
- Reading a long contract, a request for proposal or a lender agreement and listing the terms that deserve a second look.
- Building the quarterly narrative for your board or owners from the numbers and your notes.
- Explaining a complicated spreadsheet model, or writing the formulas yourself, with AI in Excel.
- Research on a competitor, an acquisition target or a new market, with sources you can open.
What other ways are there to learn AI in Chicago?
Executive programs at the business schools. Chicago Booth's The AI-Ready Leader and Kellogg's Leading with AI are in-person programs in Chicago for leaders who want strategy, a cohort and a credential.
A team workshop gives the leadership group one baseline and one set of rules for sensitive data. If you'd like that, we can scope it on the intro call.
Online courses at your own pace are inexpensive and fine for vocabulary, though they won't touch your own files.
1-on-1 coaching skips the general curriculum: every minute is spent on your material, and I correct how you use the tools in real time. To compare the formats on cost and time, read my overview of AI coaching for executives.
Start here
Book a complimentary 30-minute intro call
We'll talk through your work, pick the session that fits, and set a date, in person or remote, before you pay anything.
Your coach
Coached by Pete Enestrom
Yale and Columbia grad, former Microsoft and Intel, and a venture-backed exited founder. Pete has spent the last four and a half years going deep on every major AI tool, and he teaches the way operators learn: on your real work, at your pace, with nothing assumed.
Common questions
Straight answers, the way I'd give them across a table.
Yes. I travel to Chicago from Greenwich, CT, where I'm based, and meet you at your office downtown or in the suburbs. We set the date on the complimentary 30-minute intro call.
The two-hour Deep Dive costs $1,000 and the half-day Intensive costs $3,500, the same in Chicago as anywhere else, in person or remote. The 30-minute intro call that comes first is complimentary.
If your leadership team wants to learn together, tell me on the intro call. We'll scope a workshop around your team's real work and your company's rules for confidential information. One-on-one sessions for individual executives can follow.
Yes, on the executive's side of the business: operations reports, supplier and customer letters, contracts, and the numbers behind them. The tools summarize and draft well but can get figures wrong, so we always check numbers against the source. For more examples, see AI in manufacturing.
Yes. Oak Brook, Schaumburg and the North Shore are all in my Chicago travel area, along with downtown. Tell me where your office is when we talk and we'll plan around it.
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