Future Billing for Manually Entered Users - Protected Content

I'm going to be adding members to the protected content plugin manually for a membership option that has an annual recurring payment. How do I ensure that they are billed for the first time on the correct date?

For example, I have a member who already paid us in June of this year. After I add them manually as a member via the plugin, how to I make sure that member begins annual recurring billing for the membership type I added them to in June of next year? Thanks!