For the dough:
1 cup (8 oz.) unsalted butter, at room temperature
4 oz. cream cheese, at room temperature
½ cup brown sugar
½ cup granulated sugar
1 tbsp. vanilla extract
½ cup pecans, finely chopped
¼ tsp. salt
2½ cups all-purpose flour
For the filling:
¼ cup (2 oz.) unsalted butter, melted
¼ cup granulated sugar
¼ cup light corn syrup
1 large egg yolk
2 tsp. vanilla extract (or bourbon)
Pinch of coarse salt
1 cup pecans, coarsely chopped
For the caramel drizzle:
4 oz. caramel candies, unwrapped
2 tbsp. heavy cream, plus more as needed
To make the dough, combine the butter and cream cheese in the bowl of an electric mixer. Beat on medium-high speed until well blended, about 1 minute. Mix in the sugars and beat on medium-high until light and fluffy, about 2-3 minutes more. Blend in the vanilla extract. With the mixer on low speed, mix in the pecans, salt, and flour just until fully incorporated. Cover the bowl and transfer to the refrigerator. Chill the dough for about 30-60 minutes.
While the dough is chilling, make the filling. In a medium bowl, combine the melted butter, sugar, corn syrup, egg yolk, vanilla, and salt. Whisk just until blended. Stir in the pecans.
Preheat the oven to 350˚ F. Line baking sheets with silicone baking mats or parchment paper. Scooping about 2 tablespoons of dough at a time, roll the dough into balls. Place the dough balls on the baking sheets 2-3 inches apart. Use your thumb (or a wine cork) to make a small round indentation in the center of each dough ball, about 1 inch in diameter. Fill each indentation with some of the pecan filling mixture.
Bake the cookies, rotating the pans halfway through, until light golden and set, about 16-18 minutes total. Cool briefly on the baking sheets, then transfer to a wire rack set over wax paper or foil. Let cool completely.
To make the caramel drizzle, combine the caramels and heavy cream in a small microwave safe bowl. Heat in 20 second intervals, stirring in between, until the caramels are fully melted and the mixture is smooth. If needed, add more cream 1 teaspoon at a time until you reach a drizzling consistency. Drizzle the caramel over the cooled cookies on the wire rack. If the caramel begins to harden, microwave for 10 more seconds and stir to rewarm.