Claude, ChatGPT or Copilot for a 20-person company
I’ve rolled out Microsoft Copilot across a whole company, and I set up Claude and ChatGPT for companies too. At 20 people the seat prices are close enough that price won’t settle it, so it comes down to how much each one can do on its own.
Prices are from each vendor’s own pages on October 12, 2026. Check again before you buy.
What a seat costs
| Plan | Per seat, paid yearly | Per seat, monthly | Fine print |
|---|---|---|---|
| Claude Team | $20 | $25 | 2 to 150 people. Claude Code included. |
| ChatGPT Business | $20 | $25 | 2-seat minimum. Codex included. |
| Microsoft 365 Copilot Business | $18 through Dec 31 ($21 list) | $25.20 | Up to 300 people, on top of a Microsoft 365 plan. |
| Gemini in Google Workspace | Included | Included | Business Standard ($14) and up for Docs, Sheets and Drive. |
Claude and ChatGPT also sell $100 premium seats for heavy users. Microsoft is renaming its product plain “Microsoft Copilot,” so you’ll see both names for a while.
Starting December 1, new Copilot Business licenses bought through a Microsoft partner also come with usage billing switched on for extras like Copilot Cowork, capped by default at 4,000 credits per person per month. Set that cap before anyone starts using it.
For 20 people, that’s about $400 a month for Claude or ChatGPT on a yearly plan, and about $360 for Copilot under its promotion plus the Microsoft plan underneath. Most of the cost is setup and training, and that’s about the same for all of them.
What decides it
What it can do on its own
ChatGPT Work and Claude’s Cowork both take a multi-step job across your apps and files, can run it on a schedule, and stop to ask before anything goes out. That’s where most of the time savings are, and it’s where Copilot is furthest behind.
Where your work lives
Copilot reads across Outlook, Teams, SharePoint and OneDrive using the permissions you already have. Clean those up first, because Copilot will find any folder that’s shared too widely.
Claude and ChatGPT connect to Microsoft 365 too, so a Microsoft shop isn’t locked into Copilot. If you’re on Google Workspace, Gemini is already paid for, so turn it on before buying anything.
Whether anyone writes code
Claude Team includes Claude Code in every standard seat, and ChatGPT Business includes Codex. With even one developer, that can settle it.
How much oversight you need
On Claude Team and ChatGPT Business, an admin decides which apps the assistant can connect to. You need the Enterprise plans for audit logs. Microsoft logs Copilot activity in Purview.
What happens to your data
None of the four train on your business data by default on these plans, going by each vendor’s own terms this month. The bigger risk is staff pasting company information into personal accounts, which is a good reason to buy a business plan at all.
How I’d choose
For most 20-person companies I’d start with Claude Team or ChatGPT Business. Copilot is a distant third for me. The rollout I ran on it worked, but ChatGPT Work and Claude’s Cowork now do far more of the work on their own. A mix is fine too, like one tool for everyone and another for your developers.
Before you buy, check what you already have. Plenty of Microsoft 365 offices have Copilot Chat free under their work login, and Workspace Business Standard includes Gemini. Use what’s free while you decide, and watch which apps your team opens first thing every morning.