Preheat the oven to 325°F. Line an 8 by 8-inch metal pan** with parchment paper, leaving an overhang. Spray with nonstick cooking spray.
Prepare the cookie layer:
In a large microwave-safe bowl, heat the butter in 30-second increments until melted.
Add the sugars to the hot butter and whisk to combine. Let cool until just warm.
Add the egg and vanilla and whisk vigorously until smooth. Stir in the flour, salt, and baking powder with a rubber spatula. Gently fold in chocolate chips.
Chill the dough in the fridge while you prepare the brownie layer.
Prepare the brownie layer:
In a large microwave-safe bowl, heat the butter in 30-second increments until melted.
Add the sugar to the hot butter and whisk to combine. Let cool until just warm.
Whisk in the egg and egg yolk vigorously for 1 minute. Whisk in the cocoa powder, oil, and vanilla. With a rubber spatula, stir in the flour, cornstarch, and salt until just combined. Fold in chocolate chips.
Assemble:
Scoop out nine 1-tablespoon portions of cookie dough and set them aside in a small bowl. Spread the remaining dough into the prepared pan in a thin, even layer. Don’t worry about making it perfect.
Spread the brownie batter evenly over the cookie layer.
Flatten the reserved cookie dough balls slightly with your palms, and place them on top of the brownie batter, letting the batter peek through.
Bake at 325°F for 33-38 minutes, until the edges are set and the cookies have very lightly begun to brown. Bake 33 minutes for a gooey, fudgy center, or closer to 38 minutes for a chewier, more set texture.
Top with flaky sea salt, then let cool in pan completely before removing and slicing.