1-on-1 AI coaching · Westchester
AI Coaching for Executives in Westchester
I'm Pete Enestrom (Zaigo Coaching), and I coach executives in Westchester 1-on-1 on using AI in their own work. Sessions are in person at your office in Westchester (I travel to you) or remote, from $1,000 for a 2-hour session, starting with a complimentary 30-minute intro call. Greenwich, where I'm based, is next door to Rye and Purchase.
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 Westchester 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 Westchester County, a short drive from Greenwich, 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 Westchester work?
Westchester County borders Greenwich, so meeting in person there is about as simple as it gets for me. Rye, Harrison and Purchase are a short drive across the state line. White Plains and Scarsdale are a little farther along the same roads, and Tarrytown sits over on the Hudson side of the county. Metro-North connects the county to Grand Central as well, which matters if you split your week between Westchester and a Manhattan office.
On the intro call we choose a date and decide where to meet. Your own desk is usually best, because that's where the files are. If your office is open-plan, a conference room or a quiet room at home works just as well. I bring nothing but a laptop; you bring the real work you want help with.
If you'd rather not block out a morning in person, the same session runs remotely: video, shared screen, same structure. If you commute into the city, a remote session may be easier to fit around the trains.
What do Westchester executives use AI for?
Westchester has a business mix all its own. Large companies keep headquarters around Purchase, Harrison and White Plains, and hospitals and health systems are major employers. Law and accounting firms in White Plains, life sciences companies along the Hudson and a long list of family businesses fill in the rest. Many senior people also live in the county and run teams in Manhattan. Whichever describes you, the useful AI work looks similar: less time on first drafts and long reading, more time on the decision.
- Turning a long internal report into a one-page summary for your leadership meeting, with the open questions listed at the end.
- Drafting a memo to staff about a change nobody will love, so the hard sentence is clear and the tone stays human.
- Preparing for a negotiation: having the tool play the other side and push back on your numbers before the real meeting.
- Reading a contract or a vendor proposal and flagging what's unusual, so you know which pages need your counsel's attention.
- Building a research brief on a market, an acquisition target or a new hire's background, with sources you can open and check.
- Cleaning up how you use email and calendar on the train, so the commute stops being lost time.
Besides 1-on-1 coaching, how can you learn AI in Westchester?
Business school programs in Manhattan are within reach. Columbia Business School's The Business of AI is an in-person executive program on generative AI and strategy, a fit if you want a cohort and a certificate.
An in-house workshop gets your leadership group to the same starting point and the same rules on confidential data. If you want one, we can scope it on the intro call.
Teaching yourself with free tools and online lessons works if you have time to experiment and the habit actually sticks.
What 1-on-1 coaching adds is focus: the whole session runs on your files and your habits, and I correct how you prompt while you work. For a side-by-side of formats, prices and time, read my comparison of executive AI training options.
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. Westchester is next door to Greenwich, where I'm based, so I meet executives at their offices in Rye, Harrison, Purchase, White Plains, Scarsdale, Tarrytown and elsewhere in the county. We agree on the date and place during the complimentary 30-minute intro call.
Two prices, same as everywhere: $1,000 for a 2-hour Deep Dive and $3,500 for a half-day Intensive. Meeting at your Westchester office doesn't change the price, and the 30-minute intro call before it is complimentary.
For most people, yes. The work happens on a screen either way: your documents, the AI tool and the prompts we write. Over video you share your screen and I watch and correct in real time.
If your leadership group wants to learn together, we can scope a workshop on the intro call, built around your team's actual work and your ground rules. One-on-one time for individual leaders can come afterward.
Yes. I work in New York City as well as Greenwich, so if your week is split between Westchester and a Manhattan office, we can meet at whichever one has your files and a quiet hour.
Keep reading
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