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The first thing you need to do is implement a Master Date so that you can show these counts on a centralized time scale. Tableau cannot "create" records (Which you need to do in order to show how many employees were active during a particular month). So the only way we can do this is either by manipulating our Data on the backend, Manipulating the Joins, or using Data Blends (But the latter greatly limits flexibility).
Here is an example of one way to do this
Thank you all - this is very insightful. I'm working through all of the suggestions and will post back with what works the best. Rody, I think your idea to create a master date is a good one. I did it with a table of each day per Kettan's warnings. I must have messed something up because the count didn't turn out to be accurate so I need to keep working that and find my error. Alexander, I think your scaffold approach makes good sense and may try that as a next solution as well.
I'll post back when I have something useful to share!