As I understand it, part of the trick is knowing how many users there really are, as compared with how many the customer says/thinks there are. One reason a lot of companies don't offer truly unlimited licenses, is that you never know when some smart alec is going to try to buy one license to be shared by the entire population of Brazil or something.
(I have nothing against Brazil, nor have I ever been comprehensively outwitted by South Americans in a business deal. I use it as an example solely because it has a lot of people in it. More likely is that the government, or MacDonald's, or someone, will get your software for $7,500 by making it seem as though they need about 1000 seats in one department, then later "change their mind" and deploy it a million times across the whole organisation, as permitted by the unlimited license).