Is it possible to synchronize Advanced Newsletter segments and lists with MailChimp?
Yes, the extension allows automatic lists and segments synchronization. It is possible to do on-the-fly or manually.
How does Advanced Newsletter auto-synchronize with MailChimp?
When auto-synchronization is turned on, the Advanced Newsletter extension and MailChimp are synchronized each time a customer is subscribed or unsubscribed in Magento store.
You can enable auto-sync feature in Backend » System » Configuration » aheadWorks Extensions » Advanced Newsletter » MailChimp configuration » MailChimp auto-sync.
Please also note, that the synchronization with MailChimp is executed by Magento cron, so it is necessary to set the latter up correctly.