It's automated in the sense that you don't have to pull a list of people who haven't activated your software, made a purchase, etc. The list will run daily/weekly, etc. and pull in the leads and send them an email.
If you have a custom object in Salesforce that houses that data (software usage, etc.) and it has a relationship to leads, contacts, or accounts, you can add that to the Salesforce sync and it will create triggers and filters from it.