AI that does real work for your business.
Practical training and custom assistants for Nantucket businesses. No hype, no mascot, no six-month transformation program.
Most AI advice aimed at small businesses stops at "try ChatGPT." That is a starting point, not a strategy.
The useful question is narrower. Which specific tasks in your week take hours, repeat constantly, and follow rules you could write down? Those are the ones worth handing to a machine. Answering the same booking question forty times. Rewriting the same event description for six channels. Pulling numbers out of invoices.
We find those tasks, then either train your team to handle them or build an assistant that does.
What we do
How it works
Most teams should start with a half-day session on-site, working through your own documents and your own recurring tasks rather than generic examples. That format sticks best, because people leave having already done the thing once with their real work in front of them.
From there it adapts. Some teams want a follow-up a month later once habits have formed. Some want it remote. Some keep us on retainer as the tools change. We will recommend one and then fit around how your business actually runs.
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01
Discovery
We map where your team's hours actually go.
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02
Pick the wins
Two or three tasks with clear rules and real time cost. Small enough to prove out.
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03
Train or build
Either your team learns the workflow, or we build the assistant, depending on which fits.
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04
Review
We check what stuck, what did not, and what is next.
Why on-island matters
Nantucket businesses have constraints that generic AI advice ignores. A season that swings from empty to overwhelmed. Staff who turn over every year. Shoulder seasons where the phone stops. Advice written for a year-round mainland company does not map cleanly onto that.
We live here. We understand what your February looks like compared to your July, and we build around it.
AI strategy and workforce training run through Nantucket AI, our sister brand. Sherry Logistics builds the software. Nantucket AI handles the training and strategy. Same people either way.
Common questions
Can you train my team to use AI tools?
Yes. Through Nantucket AI we run on-island training for small businesses covering ChatGPT, Claude, AI assistants, and agentic workflows, tailored to how each business actually works.
Is my business data safe?
It depends entirely on which tools you use and how they are configured. That is part of what we set up, and part of what the training covers.
How is the training delivered?
Most teams start with a half-day on-site session using their own documents. Remote sessions, follow-up visits, and ongoing retainers are all available, and we will tell you which one fits rather than selling you the largest option.
Will AI replace my staff?
That is not what we build. The work worth automating is the repetitive part nobody wanted, which gives your team back time for the work customers actually notice.
We are not a tech company. Is this relevant?
The businesses that get the most out of this are usually the least technical. Shops, restaurants, trades, and galleries all have repetitive written work.
What does it cost?
Training and assistant builds are both quoted as a fixed number before anything starts. What moves it is how many people are in the room, how many workflows you want covered, and whether you want something built or just want your team trained to do it themselves. Tell us the situation and you get a real number.
Not sure what AI could actually do here?
Tell us how the business runs. We will come back with two or three specific things worth automating, and be honest about what is not worth it. Prefer to talk? Call 508-257-1154.