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Preheat oven to 350°F. Grease and flour a 9x9" baking dish.
Pour Guinness into a saucepan over high heat. Reduce until ⅔ cup remains, 10-12 minutes. Pour Guinness reduction into a heat safe liquid measuring cup to cool for at least 15 minutes.
Meanwhile, add dark chocolate and butter to a medium microwave safe bowl. Melt in 30 second increments, stirring between each one until mixture is smooth.
Stir in sugar, eggs, vanilla, and ½ cup of the Guinness reduction. Add salt and flour, mixing until just combined without overmixing. Batter will be thick.
Pour batter into prepared baking dish. Bake for 30-35 minutes, or until a toothpick comes out with wet crumbs (not batter). If toothpick has batter, return to the oven and cook with 3 minute increments until wet crumbs are achieved.
Cool brownies on a wire rack for at least 2 hours until fully cooled.
Meanwhile, for the buttercream, beat softened butter until fully creamed and no lumps remain using a stand mixer or hand mixer.
Add powdered sugar and espresso powder, and mix until smooth (it will be thick and dense).
Add remaining Guinness reduction, a tablespoon at a time, until buttercream becomes light and fluffy.
Frost brownies with prepared buttercream, then cut into squares.