Vendr's data reveals significant pricing advantages when timing your Udemy negotiations strategically. For Udemy Team (2-20 users), our data shows the list price at $3,600 annually for 10 users, but companies typically achieve 17-49% discounts, bringing costs down to $1,829-$3,006. However, the real opportunity lies in understanding the Enterprise transition point. At 20 users (Team's maximum), you're paying $7,200 annually with potential savings of 23-52%, resulting in $3,456-$5,530. But here's the key insight: Udemy Enterprise starts at 21 users with a list price of approximately $40,352 for 100 users. Companies consistently achieve 21-59% discounts on Enterprise, bringing 100-user costs to $16,504-$31,918. Negotiation Strategy: If you're approaching 15+ users on Team, negotiate directly for Enterprise pricing. The per-user cost drops dramatically—from $360/user on Team to potentially $165-$319/user on Enterprise after discounts.