Preheat the oven to 325 degrees. Line a 9x13 baking dish by with parchment paper and spray it with a nonstick baking spray.
In a large bowl, add the butter, powdered sugar, granulated sugar, and vanilla. Beat with a hand mixer on medium until the butter is well combined.
Gradually add in the flour and beat until all of the flour is added. The shortbread will be crumbly but should hold it's shape when pinched together.
Take 3-4 cups of the shortbread dough and firmly press it into the bottom of your prepared pan.
Bake for 25 minutes or until the base is set and the edges are golden. Set aside to cool.
Pour the caramels and heavy cream into a saucepan and stir together on the stovetop until it’s all melted and gooey. Pour the caramel sauce over the cookie base and spread to the edges with an offset spatula.
Evenly sprinkle the chocolate chips all over the top of your caramel layer.
Using a small cookie scoop, scoop out dough balls from the remaining dough. Roll the dough into a ball and press it flat like a disc. Lay them over your chocolate chip layer allowing them to overlap a little.
Bake for 35-40 minutes until the top is golden brown. Set out at room temperature to cool completely.