At this time, Less Annoying CRM only integrates directly with Google calendar. Unfortunately, it is not possible to sync iCloud with Google calendar, however, it is possible to import events created in iCloud to Google calendar. Once the events have been imported to Google, the Google calendar sync with the CRM can be used to get the data into the CRM. There are a few different steps you’ll need to take to ensure that events end up in the appropriate place.
An important thing to note before you start the syncing process: you must have exporting privileges in the CRM in order to sync your calendar with Google. If you don't see the option to sync with Google in your account, you may not have permission to export data from your account. If you believe you should have exporting privileges, contact your account administrators.