Automessage differentiation between free blogs and supporters

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What is the best way to send different automatic messages to those who have free blogs and those who have upgraded to supporter.

When someone signs up for a free blog I want to send them automated mails encouraging them to upgrade and promises of how great it will be.

Once someone becomes a supporter then they can get more helpful automated emails and there is no longer a need to ask them to upgrade.

I cannot see how to differentiate between the two groups with automated mails. Is there some combination of method using automessage and/or mailchimp which makes this possible. I am sure there must be but can’t figure it out. Any ideas anyone?