* For companies that gated based on usage, free/trial users were much more likely to make the transition to a paying customer. For companies that gated on features, free users tried to find all kind of ways to get things done without paying for the additional functionality.
* In the early days of many companies, most of the features of the product were given away for free, with just a a handful of features gated into premium plans. As companies grew, they realized that many of the features they should have gated, were now free, leaving little incentive for the users to convert.
Hopefully this helps someone.