Make sure that the new Exec Sec has been added to the ward's MLS as a Standard Position. (Custom Positions won't work.) Then after a send/receive, you should see it listed in the CDOL.
After a day or so, then he'll get the rights to the various web apps for Exec Secs.
As for the calendar, make sure that that position is added by calling and not by name. If the latter, then you'll have to edit the rights manually. If the former, it may take a day or so before it starts to work.
However, others have reported problems with private calendars that may be your problem.
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