Free tiers must show your full magic

If it gets you to the aha moment, that path to habit formation, that has to be free. That's the core utility of your product.

What if we actually sampled a number of different paid suggestions and interspersed them to free users across their writing? All of a sudden, people were seeing Grammarly as a much more powerful tool than they were before.

Try to have your free product be a reflection of everything that your product can offer you. Obviously to an extent there's some costs involved with some of the paid features, but it generally will pay for itself if you're able to put your best foot forward.

We initially had unlimited files but only collaborate with two or three people, and that was the starter team. We realized that wait a minute, that's hurting us. And so we switched it and now it's like you can have something like three files, but unlimited collaborators.

If guilt is one of the main reasons why people are paying you, then your free version is too good, and you are leaving money on the table.