In a large stand mixer, beat the heavy cream, powdered sugar and vanilla on high until soft peaks form.
On a flat serving plate, spread a thin layer of whipped cream to hold the bottom layer of cookies in place. Arrange 7 cookies side by side in a circle, keeping 1 cookie in the center.
Spread about ⅔ cup whipped cream on top of the bottom cookie layer, making a 7-inch circle. Repeat with remaining cookies and cream, making 11 or 12 layers of cookies and ending with a layer of cream (there will be a few cookies left over - you should just eat them). Cover with plastic wrap and refrigerate overnight.
Drizzle with chocolate sauce, caramel sauce, and / or cocoa powder before serving.
Notes
These cookies are often found in the ice cream topping aisle rather than the cookie aisle. They are very thin wafers that will soften up beautifully when layered in this cake.