Preheat oven to 350℉. Line a baking sheet with parchment or a silicone baking mat.

In a medium bowl, whisk together the flour, cocoa powder, espresso powder, baking powder, baking soda, and salt. Set aside.

Add the butter to the bowl of your stand mixer fitted with the paddle attachment and beat of medium-high speed for 2-3 minutes or until light and fluffy. Add the brown sugar and granulated sugar and beat for another 1-2 minutes, scraping down the sides if needed. Add the eggs and vanilla and beat for another 1-2 minutes or until combined.

Reduce speed to low and gradually add the dry ingredients to the wet. Once incorporated, increase speed to medium-high and mix for another few seconds to make sure everything is incorporated. Add the chopped pecans and mix on medium-low until combined.

Scoop dough into 2 tablespoon sized balls and place on the cookie sheet 2 inches apart. Press a whole pecan on top of each dough ball. Bake for 12-14 minutes or until set. Let cookies rest for a few minutes on the baking sheet before transferring to a wire rack to cool the rest of the way (the will be very delicate when hot!) Once cooled, drizzle with the salted caramel and sprinkle with flaky sea salt.

In a medium saucepan, bring the sugar and water to a boil over high heat. Cook until the sugar is dissolved, but DO NOT stir! Swirl the pan on the stove if you need to. Continue cooking, without stirring, until an amber caramel forms, about 6-7 minutes. Remove from the heat and carefully stir in the cream, and continue to stir until smooth. Add the butter, vanilla, and salt, and stir until combined and the butter is melted. Let cool.