ClickUp’s headline price of $7/user/month is the most aggressive in project management. The actual cost for a 20-person Business team with Brain AI, Email ClickApp, and sales tax runs $5,648/year — 96% above the plan page figure. Brain AI at $9/user/month is workspace-wide: you pay for every seat whether they use AI or not. Guest-to-member auto-conversion fires without warning. Automation limits on Unlimited expire in under 3 weeks for any active agency workflow.