The pricing gap between Teams Standard and Teams AI is substantial but often misunderstood. Our data reveals Teams AI costs approximately $1,749 per user annually (based on 50-user deployments at $87,450 list price), while Teams Standard runs about $1,499 per user. However, this $250 per user premium includes built-in AI capabilities that would cost significantly more as separate add-ons. Here's the critical insight: If you need AI Assistant for more than 30% of your team, Teams AI becomes cost-effective. Adding AI Assistant separately to Teams Standard costs $1,200 per user annually, making the total $2,699 per AI-enabled user versus $1,749 for Teams AI. Financial breakeven analysis: For a 50-user team, if 15+ users need AI capabilities, Teams AI saves approximately $14,250 annually compared to adding AI Assistant to Teams Standard. Companies achieving the 85th percentile discount (14% off Teams AI) can secure 50 licenses for $75,207 versus $89,475 for the mixed approach – a $14,268 annual savings while providing AI access to all users.