Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
In a stand mixer, combine the softened butter and powdered sugar until smooth and fluffy. Gradually add the vanilla extract, all-purpose flour, and salt until a soft dough forms.
Roll the dough to a thickness of about ¼-1/2 inch, cut shapes with your favorite cookie cutter, and bake for 10-12 minutes, or until edges are lightly golden.
In a microwave-safe bowl, combine caramel bits with heavy cream and microwave in bursts until smooth. Spoon over cooled cookies.
Melt the milk chocolate chips with coconut oil and pour over the caramel layer, spreading evenly. Allow cookies to cool completely to set.
Notes
For an elevated flavor, sprinkle a pinch of sea salt on top of the chocolate layer.