Pre heat the oven to 350 degrees F˚ with the rack in the upper third. Lightly butter a 10 inch cast iron skillet. Set aside.
Using a double boiler or place a medium medium bowl over a pot with 1 1/2 inch simmering water. Melt the chocolate chips with the butter and oil. Mix until melted and combined.
Remove the bowl from the heat and mix in both sugars. The mixture will be grainy and that's OK. Let sit to cool 10-15 minutes.
In a medium bowl whisk together the flour, baking powder and salt, set aside.
Mix the eggs one at a time into the chocolate mixture until well combined. Mix in the vanilla and coffee.
Add the flour mixture into the chocolate mixture, mix until just incorporated. Don't over mix.
Pour the brownie batter into the prepared skillet, smooth out the top with a spatula.
Bake for 30-33 minutes or until a toothpick comes out virtually crumb free.
Let the brownie cool completely before serving. Add whipped cream to the top when ready to serve.
While the brownie is baking make the whipped cream. Pour the cold cream into the bowl of a stand mixer. Using the whisk attachment, whisk on low speed until the cream starts to thicken. Add the maple syrup, continue to whisk on medium, then high speed as the cream thickens. Continue until you have stiff peaks the total time will be about 5-6 minutes. Whisk in additional maple syrup if you want it sweeter. Store in the fridge until ready to use.