Good question Brian. I am always a fan of a free trials or even better, the free tier. The later you have to watch out as you could be stuck a situation where you can't convert people to the higher tiers, but all in all what you are trying to do is show people the value your product provides and the best way is to have them see it with their own eyes. Once the user sees the value your product brings them then they will easily jump on board to becoming a paid customer. Also, be sure to get feedback from your users, especially ones who convert to paid customers. You could interview them or survey them understanding what value they got out of the product, but the paid customer provides the best insight, none paid can sometimes have you chasing your tail! Good luck and keep hustling!