Quick Question: I already have a Masters, is it worth it to get another Master degree at a top program?

Quick Answer: Generally speaking, unless you want to go into a career in academics (in which case you actually want to get a PhD rather than numerous masters degrees), most employers prefer to see work experience rather than multiple degrees. Many admissions committees are also wary of applicants who appear to be “career students” so an existing masters can sometimes make it harder to get in.

Like I said though, the more important factor to consider is the impact on your career and most hiring managers would prefer to see you spend your two years getting real work experience where you can demonstrate impact and drive results.