Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper.
In a large bowl, combine flour and powdered sugar. Cut in cold butter using a pastry blender or your fingers until the mixture resembles coarse crumbs.
Press the dough into the bottom of a 9x13 inch baking pan. Bake for 15-20 minutes, or until lightly golden.
Meanwhile, make the caramel: In a saucepan, combine brown sugar, corn syrup, and heavy cream. Bring to a boil over medium heat, stirring constantly. Reduce heat and simmer for 5 minutes, or until thickened.
Pour the caramel over the baked shortbread crust. Let cool completely.
Melt chocolate. Spread over the caramel layer.
Refrigerate for at least 30 minutes before cutting into bars.