To extend upon @annaS’s idea, using smart list membership as re-enrollment criteria should work, but only if you’ve added criteria to remove someone from the list after a period of time. If your criteria is “Deal stage” is equal to “Closed/Won”, the contact will never be removed from the list, and as a result, won’t trigger the re-enrollment criteria of “list membership” in your workflow. That enrollment criteria is based off of new list membership, not current.
The trick is to add criteria that has a rolling date. @brianweiss had an awesome idea to add the contact property, “Recent Deal Close Date” and use the rolling criteria of “is less than”, followed by the amount of time you’d like to specify. A week or shorter should suffice.
What this means is, your contact will be added to the list the moment they have a deal that has reached “Closed/Won” less than a week ago, and removed when the deal’s close date is no longer within that window. This will allow you to have the same contact added to the list multiple times, resulting in workflow re-enrollment.
The exact criteria should look like this:
Deal Property > “Deal Stage” is equal to “Closed/Won”
AND
Contact Property> “Recent Deal Close Date” is less than “1 week”