1-on-1 AI coaching · Boston
AI Coaching for Executives in Boston
I'm Pete Enestrom (Zaigo Coaching), and I coach executives in Boston 1-on-1 on using AI in their own work. Sessions are in person at your office in Boston (I travel to you) or remote, from $1,000 for a 2-hour session, starting with a complimentary 30-minute intro call. That includes Cambridge, Waltham and the Route 128 corridor, and Providence too.
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 Boston 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 Greater Boston (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 sessions in Boston work?
I'm based in Greenwich, Connecticut, and I travel to Boston for in-person sessions. That covers downtown and the Back Bay, Cambridge, and the suburban office parks in Waltham and the rest of the Route 128 corridor. Providence, Rhode Island is a nearby trip on the same route, and I come there too.
Because I'm traveling, we fix the date on the intro call. On the day I come to your office and we work on your real material for two hours or a half-day. There's no setup beyond your laptop and access to the tools you want to learn.
Not every week allows for a visit. A remote session is the same work over video, with your screen shared, and it's a good way to start before we meet in person in Boston.
What do Boston executives use AI for?
Boston's economy is built on knowledge work. Life sciences and biotech cluster in Cambridge, hospitals and universities are among the region's anchors, asset management and financial services sit downtown, and technology companies line Route 128. Leaders here read more than most: papers, filings, research summaries and long reports. A session puts AI to work on that reading and on the writing that follows.
- Getting through technical or scientific material you need to understand but didn't write, with the tool explaining it at the level you need.
- Turning a long research report or a data-room document into the five points that matter for your decision.
- Drafting grant, partnership or investor narratives from your notes, then tightening them in your own voice.
- Board and leadership prep: a pre-read, likely questions, and a stress test of the plan before you present it.
- Comparing vendor or partner proposals side by side and writing the follow-up questions.
- Using research tools such as Perplexity to get sourced answers you can check, instead of a confident guess.
What other ways are there to learn AI in Boston?
University executive education. MIT Sloan's Artificial Intelligence: Implications for Business Strategy is a self-paced online course for leaders who want the strategic picture and a certificate.
Workshops for a leadership team or department build a common vocabulary and common rules. If your team needs that, we can scope a workshop on the intro call.
Online courses and the providers' own free lessons are useful for the basics if you have time to practice on your own.
1-on-1 coaching is the most personal of these: two hours or a half-day spent only on your documents, with someone watching how you work and correcting it in real time. I've put the formats side by side, with published prices, in my guide to executive AI coaching and its alternatives.
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, CT and travel to Greater Boston for in-person sessions: downtown, the Back Bay, Cambridge, Waltham and the Route 128 corridor. We fix the date on the complimentary 30-minute intro call.
The Deep Dive is $1,000 for two hours and the Intensive is $3,500 for a half-day. Those are the session prices whether we meet at your Boston office or online, and the intro call beforehand is complimentary.
If you want the leadership team to learn together, mention it on the intro call. We'll scope a workshop around your team's work and your rules for confidential material, and 1-on-1 sessions for individual leaders can follow.
Yes, for the leadership side of the job: reading papers and reports you didn't write, summarizing them, and writing for boards, partners and investors. AI tools can misstate scientific detail, so we check claims against the source. Unpublished data and anything under confidentiality stays out unless your company's policy allows it.
Yes. Providence, Rhode Island is a nearby trip, and I meet executives there in person as well. The format, price and booking are the same as for Boston.
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