While cookies are baking or chilling, make the cheesecake topping.
In a clean stand mixer fitted with the paddle attachment, add the softened cream cheese and softened butter.
Whip very well on medium speed for 3-4 minutes until cream cheese and butter and light, fluffy, and well combined. Scrape down the edges and mix again for 1 minute.
Then add in the vanilla and add the powdered sugar (slowly, 1 cup at a time).
Continue to whip and scrape down until the filling is creamy and well combined. If there are any clumps, keep whipping on high for 4-5 minutes until it's light and fluffy. It should be very smooth!