We are asked this every week, and the honest first answer is that at the level a twenty-person business uses them, both are excellent, and any ranking of the underlying models will be out of date by the time you read it. We build on Claude and we say so, so read what follows with that in mind. But the reasons a team ends up using one of these tools every day, or abandoning it by the spring, have very little to do with the leaderboard. They are about how it is bought, set up and run.
Business plan or personal accounts
The biggest single mistake is letting everyone sign up personally and expense it. Personal accounts sit outside your control: no shared workspace, no admin, no way to remove access when someone leaves, and different data terms. Both Anthropic and OpenAI offer business tiers with an admin console, shared spaces and the promise that your data is not used to train their models. Whichever you choose, choose the business plan. This is not a Claude-versus-ChatGPT question; it is the question that comes before it.
Data and training terms
On business plans, both vendors state that customer content is not used to train models. Read the current terms rather than a blog post, including this one, because they change. What you are looking for is a plain statement that your inputs and outputs are not training data, a clear retention period, and a data processing agreement you can sign. Both offer these. Your compliance adviser will want the documents, so ask for them before, not after, the team is using it.
Shared projects and knowledge
Where the two differ more is in how they let a team share context. Claude's Projects let you give a workspace a set of documents and instructions once, so that everyone drafting client emails works from the same tone guide, or everyone in accounts sees the same process notes. ChatGPT has its own equivalents and they have improved quickly. In practice, what matters is whether anyone builds these spaces at all. A workspace with six well-made shared projects gets used. A blank one does not, whichever logo is on it.
Admin, SSO and leaving
For a team, the boring features are the important ones. Can you add and remove people centrally? Can you see who is using it? Can you connect it to your Google Workspace or Microsoft 365 login so there is one password to revoke when someone leaves? On the higher business tiers both support single sign-on and provisioning; on the entry tiers, check. If you are regulated, the audit log matters too: who did what, when.
Connections to your tools
Both now connect to the tools a small business runs on: email, calendars, drives, and a growing set of third-party systems. Claude does this through a connector standard that a lot of software vendors have adopted; ChatGPT has its own route. The question to ask is not 'does it integrate' but 'does it integrate with the three systems we actually use', and to get a demo of that, on your accounts.
Cost
Per seat, the business plans are similar and both are small next to a salary. The cost that matters is the setup nobody budgets for: writing a usage policy, deciding what may and may not go into the tool, building the shared projects, connecting the systems and training people on it. That fortnight is the difference between a team that uses the tool daily and one that forgot it existed. It costs about the same whichever vendor you choose.
How to decide
If your team lives in Google Workspace or Microsoft 365, check which connects more cleanly to what you have. If you handle regulated data, put both sets of terms in front of your adviser and let them choose. If you already have a house style and a set of processes, pick whichever lets you encode them as shared context most easily. And if none of those tips it, choose the one whose way of talking your people prefer, because the tool they enjoy using is the one they will use.
Then, whichever it is, set it up properly. That is where the return lives.