1-on-1 AI coaching · Connecticut
AI Coaching for Executives in Connecticut
I'm Pete Enestrom (Zaigo Coaching), and I coach executives in Connecticut 1-on-1 on using AI in their own work. Sessions are in person at your office in Connecticut (I travel to you) or remote, from $1,000 for a 2-hour session, starting with a complimentary 30-minute intro call. Greenwich is my home base, so anywhere from Stamford to Hartford is close.
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 Connecticut 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 Connecticut (Greenwich is my home base), 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 sessions in Connecticut work?
Connecticut is the easiest place for me to meet in person, because I'm based in Greenwich. Greenwich, Darien and New Canaan are a few minutes away. Stamford, Norwalk and Westport sit a short trip up I-95 or the Metro-North New Haven Line, and so does the rest of Fairfield County. Hartford is a longer drive, and I make it for in-person sessions too.
We pick the date together on the complimentary intro call. On the day, I come to your office, we close the door, and we spend two hours or a half-day on whatever is actually on your desk that week. You need your laptop, your documents and a login to the AI tools you want to learn. A conference room works as well as your own office.
Remote is the same session over video with a shared screen, and it suits weeks when travel or a board meeting eats your calendar. You can also mix the two: a first session in person in Connecticut, and later ones remote.
What do Connecticut executives work on with AI?
Business in Connecticut leans toward finance and insurance: investment firms and family offices in Fairfield County, insurers around Hartford, and corporate headquarters in Stamford and along the I-95 corridor, with plenty of owner-led companies alongside them. The common thread is a week of reading, writing and judgment calls. That's the work AI helps with most, so that's what a session runs on.
- Investor letters and quarterly updates: a first draft built from your notes and written in your voice, so you edit instead of starting cold.
- Long documents: an offering memo, a policy wording or a lease read with you, the clauses that matter pulled out, and the questions you should ask next.
- Investment committee and board prep: a thick pack cut to a one-page pre-read, then the tool argues the skeptic's side before the meeting does.
- Research before a call: a company, a sector or a counterparty summarized with sources you can check.
- Spreadsheets: formulas written for you and an inherited model explained step by step, using AI in Excel.
- The email you keep putting off, to a partner, a client or an employee, drafted plainly in a few minutes.
What are the other ways to learn AI in Connecticut?
University programs. Yale School of Management's executive education offers a short online course on AI for pricing decisions, aimed at leaders who set prices. For a broader executive program, Columbia Business School's The Business of AI runs in person at Columbia's Manhattanville campus in New York City. Programs like these suit you if you want frameworks, a certificate and a group of peers.
A workshop for your leadership team gives everyone the same baseline and the same ground rules for confidential material. If that's what you need, we can scope one on the intro call.
Self-paced online courses are inexpensive or free and good for vocabulary, but the exercises are generic, and nobody opens your files.
One-on-one coaching differs from all three in a single way: every minute goes to your own work, at your pace, with me correcting how you use the tool as you go. See how the formats compare on time and price.
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'm based in Greenwich, so I meet clients in person across Connecticut: Greenwich, Stamford, Darien, New Canaan, Westport, Norwalk, the rest of Fairfield County, and Hartford. We set the date on the complimentary 30-minute intro call.
The 2-hour Deep Dive is $1,000 and the half-day Intensive is $3,500, whether we meet at your office in Connecticut or over video. You start with a complimentary 30-minute intro call, so you know it's the right fit before paying anything.
Yes. A remote session is the same two hours or half-day over video, with your screen shared so I can see how you prompt. Plenty of the work is easier that way, because your files are already on your computer.
If you want your leadership team trained together, raise it on the intro call and we'll scope a workshop around your team's work and your rules for confidential material. One-on-one sessions for the principals can follow.
Sometimes, with care. What's safe depends on your firm's AI plan and written policy. Business and enterprise plans from the major providers don't train on customer content by default; consumer plans can, unless you change the setting. Before we open any files, we agree on what stays out of the tools. More in ChatGPT privacy in plain English.
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