In a bowl, toss the sliced strawberries with the granulated sugar. Let them sit for about 15-20 minutes to macerate and release their juices.
While the strawberries are macerating, whip the cold heavy cream in a large bowl with an electric mixer until soft peaks form. Gradually add the powdered sugar and vanilla extract, and continue whipping until stiff peaks form. Be careful not to over-whip.
To assemble the cake, spread a thin layer of whipped cream on the bottom of a 9×13 inch baking dish or serving platter.
Arrange a single layer of cookies over the whipped cream, breaking them to fit as needed.
Spoon about half of the macerated strawberries and their juices over the cookie layer.
Spread about one-third of the remaining whipped cream over the strawberries.
Repeat the layers: another layer of cookies, the remaining strawberries and juices, and another third of the whipped cream.
Top with a final layer of cookies and the remaining whipped cream, spreading it evenly.
Cover the dish tightly with plastic wrap.
Refrigerate for at least 4 hours, or preferably overnight, to allow the cookies to soften and the flavors to meld.