Preheat the oven to 350℉. Butter a 9x9-inch baking dish and set aside.
Place all of the ingredients for the pumpkin layer into a mixing bowl. Using a hand mixer, mix until combined. Set aside.
Place all of the dry ingredients into another mixing bowl. Whisk together and set aside.
Melt the chocolate. Bring a small pot of water to a simmer. Place a glass or metal bowl over the pot. The bowl should fit into the top so that the sides are partially covered and not touching the simmering water. Add the butter and chocolate to the bowl. Using a rubber spatula scrape the sides of the bowl and stir often to combine until smooth and silky, about 6-8 minutes. Remove from the heat to cool for 5 minutes.
In another bowl, mix sugar, oil, espresso, eggs, and vanilla.
Slowly add ½ cup of the cooled chocolate to the sugar mixture. Whisk until smooth to temper the egg and sugar mixture. Add the rest of the chocolate and mix until smooth.
Next, transfer the flour to the chocolate and fold it together. Transfer the brownies to a baking dish. Pour the pumpkin mixture over the top and spread. Using a knife swirl the pumpkin into the brownies.
Bake for 45-55 minutes using the toothpick test to determine doneness.
Allow the brownies to cool for at least 10 minutes before transferring from the baking dish.