Three subscriptions, similar promises — this week the column puts them side by side for a
small Jamaican office. (Branded graphic by PGH Consulting, LLC)
By now somebody has told you that your business needs AI. Perhaps it was your accountant, who swears by ChatGPT. Perhaps your IT support company, which wants you on Copilot because the office already runs on Microsoft 365. Perhaps your daughter, home from university, who does everything in Claude. The advice is confident, contradictory, and rarely comes with prices attached — and the three subscription pages read like the same brochure with different logos.
This column has now spent seven weeks using these tools on real finance work — spreadsheets, cash flow forecasts, receipts, dashboards, slides, and last week an agent that drafts variance commentary. So this week, the comparison, with one caveat up front: all three are good, all three are improving quickly, and the right answer depends far more on how your office already works than on any league table. Prices and features below were checked the week of writing, and they change often — treat them as a snapshot, not scripture.
The most useful question is not “which AI is smartest?” but “where does my work already
happen?” (Branded graphic by PGH Consulting, LLC)
Start with where your documents live
The most useful question is not “which AI is smartest?” It is “where does my work already happen?” If your office lives in Word, Excel, Outlook, and Teams on a Microsoft 365 business plan, Copilot starts with home advantage: it sits inside the tools your staff already have open, and there is no new habit to build. If your office runs on Google Workspace, or on a mix of tools, a chat-first assistant like ChatGPT or Claude is the more natural fit — you bring the work to it, as this column has done for most of the series. Fit beats features. The best tool is the one your team will actually open on a busy Thursday.
What each one does best: the all-rounder, the long-document writer, and the layer inside
Microsoft 365. (Branded graphic by PGH Consulting, LLC)
What each one does best
ChatGPT is the all-rounder and, for most people, the first tool they ever tried. It is strong at exactly the everyday mix a small office throws at it: draft this letter, explain this clause, analyse this export, give me five options for handling a difficult customer. Its data analysis mode does real work on spreadsheets, and the mobile app is polished enough that plenty of owners run their whole relationship with it from a phone. Week 1 of this column was built on ChatGPT inside Google Sheets, and it remains the easiest on-ramp.
Claude is the strongest writer of the three to my eye, and it shines on long documents: hand it a lengthy contract, a bank facility letter, or a year of messy files and it works through them patiently and carefully. Weeks 2, 5, and 6 of this column — the cash flow forecast, the receipts cleanup, the Excel-to-slides workflow — were all Claude jobs. If your painful work is reading and drafting around big documents, it earns its seat quickly.
Copilot is less a separate destination than a layer over Microsoft 365: it drafts the email in Outlook, summarises the thread in Teams, and builds on your files in Word and Excel. Its distinctive strength is the one Week 7 covered — agents your team shares, grounded in your SharePoint folders, applying your standing instructions every month. For an office already paying Microsoft every month, it is the shortest path to AI showing up where the work is.
Closer in price than the marketing suggests: roughly US$20 a head per month, whichever logo
you pick — start with one or two seats. (Branded graphic by PGH Consulting, LLC)
What they cost
For a small team, the entry business tiers are closer in price than the marketing suggests. ChatGPT’s Business plan (the renamed Team plan) runs about US$25 per user per month, or US$20 on an annual commitment, with a two-seat minimum. Claude’s Team plan is priced almost identically: about US$25 per user monthly, US$20 annually, for teams from two seats up. Microsoft now sells a small-business tier, Microsoft 365 Copilot for Business, at a promotional rate of about US$18 per user per month on an annual term (standard US$21) — but it sits on top of a Microsoft 365 business subscription, so it is an add-on to what you already pay, not a substitute. Call it roughly US$20 a head per month whichever way you go: for a five-person office, about US$100–125 a month, or somewhere around J$16,000–20,000. That is a real line item for a small Jamaican business, which is why the sensible move is one or two seats for the people who own reporting and paperwork first, not a licence for everyone on day one.
The rule that matters more than the logo: buy the business plan, and write the one-page policy
before you buy anything. (Branded graphic by PGH Consulting, LLC)
The rule that matters more than the logo
Here is the part that matters more than the brand on the tab. On all three business tiers — ChatGPT Business, Claude Team, and Microsoft 365 Copilot — your prompts and files are not used to train the underlying models; that protection is part of the commercial terms. The free and personal versions are a different story, with data settings that vary and default behaviours you have to check. So the real risk in most offices is not the tool the business chose; it is the staff member quietly pasting the payroll summary into a free personal account because the office never gave them a proper one. Whichever assistant you pick, pair it with a one-page policy: use the business account only, never paste customer data or salary information, and treat anything price-sensitive the way you would treat it with an outside consultant. This column’s standing rule travels across all three logos unchanged.
What none of them will do
No subscription changes the discipline this series keeps returning to. None of these tools knows your business, your customers, or why April was slow. All three will occasionally state something wrong with total confidence, and all three can mangle a figure when moving it from a table into a sentence. None of them should ever be allowed to generate a number that goes to your bank, your board, or Tax Administration Jamaica — figures come from your books, and every draft gets checked against them. The subscription buys you a tireless drafting assistant, not a finance department. The judgement stays with you, whichever box you tick.
What to try this week
1. Write down the three tasks that eat the most drafting and reading time in your office — those, not the demos, are what you are buying a tool for.
2. Run one of those tasks through the free tier of ChatGPT and Claude using dummy or non-sensitive data, and compare the results side by side.
3. Check what your office already pays for: if you are on a Microsoft 365 business plan, price the Copilot for Business add-on against a standalone subscription.
4. Price it for the team you actually have — start with one or two seats for the people who own reporting, not licences for the whole office.
5. Draft the one-page AI policy before you buy anything: business accounts only, no customer or salary data, and every figure verified before it leaves the office.
Test with dummy data only until you are on a business plan, and reconfirm prices and terms on the vendors’ own pages before you subscribe — they change often.
Peta-Gaye Hardy is the founder of PGH Consulting, LLC, where she helps finance and operations teams adopt AI in practical, low-risk ways. She writes the weekly AI in Finance & Business column and is based between Jamaica and the United States. Learn more at www.pghconsultinggroup.com. Follow on Instagram @pghconsultinggroup.
Disclosures: This article is informational and does not constitute investment, tax, legal, or accounting advice. AI tools can produce errors and figures should always be verified against source data. Pricing and features are as published by the vendors at the time of writing (July 2026) and are subject to change; promotional rates may expire and prices exclude applicable taxes. The author has no commercial relationship with OpenAI, Anthropic, Microsoft, or any product mentioned and was not compensated by them. Readers should consult a qualified professional before acting.