Prices, checked October 2026
| Tool | Free tier | Paid individual plan | Business option |
|---|---|---|---|
| ChatGPT | Yes | Plus: $20/month (OpenAI) | Business plans from 2 users (pricing) |
| Claude | Yes | Pro: $20/month monthly, $17/month annual (Anthropic) | Team plan for 2 to 150 people |
| Gemini | Yes | Google AI Pro: $19.99/month (Google) | Gemini Enterprise Business edition from $21/seat/month |
Plans change often. Treat this table as a starting point and confirm on each vendor's page before you buy.
Decide by the tools you already use
- Google Workspace business (Gmail, Docs, Drive): start with Gemini. Google's business edition lists connections to Google Workspace and Microsoft 365, HubSpot and other tools.
- Microsoft 365 business (Outlook, Word, Excel): compare Microsoft Copilot with Claude. Anthropic's pricing page lists Claude for Microsoft 365 and Outlook on its Pro plan, and ChatGPT Plus lists Excel, Word, PowerPoint and Google Sheets extensions.
- Mostly phone, texts and field software: the ecosystem matters less. Pick the one whose mobile app and voice mode you like using, because you'll use it from the truck or the floor.
The assistant that sits inside the apps where your work already happens gets used. The "best" one you have to copy and paste into often doesn't.
The three-task test
Benchmarks measure things you probably don't do. Instead, take three real tasks from last week and run each one through two or three assistants on their free tiers:
- A writing task: a quote cover email, a proposal section or a reply to an unhappy customer.
- A summarizing task: a long email thread, call notes or a supplier contract (remove anything confidential first).
- A spreadsheet or numbers task: explain a report, build a formula or tidy a messy list.
Use the same prompt in each. Score them on how much you had to fix, whether they made things up, and whether the tone sounds like you. Pay for the winner, for one person, for one month, then decide whether the team needs it.
I run a [type of business] with [number] people. Here's a real task: [paste]. Do it the way an experienced office manager in my industry would. If you need information you don't have, ask me rather than guessing.
Data and privacy: what to check
Read the data terms for the exact plan you buy, not the product in general. For example, Anthropic's pricing page shows model training as opt-out on its individual plans and none by default on Team and Enterprise. OpenAI separates individual plans (Free, Go, Plus) from Business and Enterprise plans for organizations. For anything client-confidential or regulated, use a business plan with the right agreement in place, and set a team policy first. Our one-page AI policy takes ten minutes.
Do you need more than one?
Usually not at first. One shared tool, used consistently, beats three tools used occasionally. Some owners keep a second free account for comparison. Add a second paid tool only when a specific task clearly works better there.
What changes when we refresh this guide
We recheck prices, plan names and business features each quarter and update the date at the top. If something on this page no longer matches a vendor's page, the vendor's page is right.
Choosing the assistant is the easy part. Your business's AI plan covers what to use it for in your kind of business and which tasks justify paid tools, with a monthly cost for each.