The devs can, sure. The "enterprise plan" is more for that + giving Claude to all the non-technical employees for access to the chatbot + Cowork. Plus SSO and all that jazz.

They can do that, but I expect they see individual user accounts and enterprise account management and easy rollout of Claude.ai/Cowork/Claude Code/etc as worth an extra $20/month/person.

Your CISO is paying to not be responsible. That’s it. That’s always the reason.

Enterprises can, but then they have to show their auditors that this has been done in a way which is robust and can’t be bypassed, and they have to build the kind of reports people need to be convinced of that — nothing is ever “just” in enterprise IT.

Longer term, you also have to be careful about building things around details which could change at any time. OpenAI and Anthropic have a ton of pressure to start banking huge profits and they very closely monitor customer activity. A time-honored strategy in this space is to shuffle the features enterprise customers depend on but which aren’t deal-breakers for most other customers into expensive enterprise plans. There’s possibly some counter pressure from companies like Google which have healthier finances but I wouldn’t count on that since they also have MBAs who’d be all too happy to invent pretexts to hike their prices to match.