They do need to break down their pricing structure in a way that people can easily buy into their service. The big issue here is the sheer amount of difference

They do need to break down their pricing structure in a way that people can easily buy into their service. The big issue here is the sheer amount of difference between the free plan and the lowest priced plan. In order to get people into your monthly billing cycle you must focus on getting them to take little steps. First get them to sign up. Then move them to a free plan. It doesn't matter if its profitable, just get them to overcome the barrier of taking out their credit card. Second step is to get them to upgrade their plan to a profitable one. This is much more easy because they are your customers. No need to pitch them the idea anymore. All you need to do is show them that the other plan meets their needs. You can also upgrade them for free for a limited time (say 3 months) to overcome the barrier of upgrading, and then start charging them at the upgraded pricing. This way they get to integrate into the new plan. They will feel the pain of downgrading, and will mostly decide to not do so. Third, you upsell additional services not included in plans. Use the same technique in the second step. Give them free trials, and start billing automatically once the trial is over. They can always cancel, but most won't bother or want because they have already been using the product for so long. Realize that people will pay money in order to not lose something. This is a very strong mechanism to use to increase the profitability of your products.