Preheat oven to 350°F (175°C) and grease an 8x8 inch baking pan or line with parchment paper.
Prepare the brownie layer: In a medium bowl, whisk melted butter and sugar. Add egg and vanilla, whisking until combined. Fold in cocoa powder, flour, and salt until just smooth. Spread evenly into the bottom of the prepared pan.
Prepare the cookie layer: In a separate large bowl, cream together softened butter, brown sugar, and granulated sugar until light and fluffy. Beat in the egg and vanilla.
Whisk together flour, baking soda, and salt. Gradually add to the wet cookie ingredients until just combined. Stir in chocolate chips.
Drop spoonfuls of the cookie dough over the brownie batter and gently spread or press down to cover the surface.
Bake for 30 to 35 minutes, or until a toothpick inserted into the center comes out with a few moist crumbs.
Allow to cool completely in the pan before slicing into 16 squares.