When you are doing a CSV import to a category that is already on a store or a company that has users on a store, in the second stage "Import Options" you need to expand Advanced Options and check the box for "RUN SERVER SUITESCRIPT AND TRIGGER WORKFLOWS". This should allow our syncing event listeners to fire to let our system know something has changed.

Keep in mind that this is not necessary or recommended (it would be wasteful and add to your que) when adding products or users for a new store that has not been connected yet. Only products in categories and users in company customers that are currently in use require this.