As Craig Walker, Founder and CEO at DialPad notes, We made our free service almost too good, so we have a lot of very dedicated, very happy free users, and sometimes we have a hard time upselling them because they’re like, “Hey, why would I need anything else?” Our stiffest competition is coming from ourselves! On the other hand, it’s also way too easy to give away too little. By doing so, you make it extremely hard for new users to see value in your product—the powerful, fun features are hidden behind closed doors.
