First, mix the espresso powder, 2 tablespoons of maple syrup, and heavy whipping cream in the bowl of a stand mixer. Set aside to bloom for 5-10 minutes.
Next, add the pumpkin puree, blended cottage cheese, 2 tablespoons of syrup, cinnamon, and 1 teaspoon of vanilla extract to a large bowl. Stir to combine. Set aside.
Using the whip attachment, turn the stand mixer on high and whip until stiff peaks form.
Assemble the tiramisu. Lay half of the Nilla wafers on the bottom of an 8x8-inch dish, making sure they overlap slightly.
Scoop half of the pumpkin mixture and spread it on top of the Nilla wafers.
Then spread half of the whipped topping on top of the pumpkin layer.
Repeat the layers until all of the ingredients have been used. Top with sifted cocoa powder and refrigerate for 20 minutes.
Serve topped with more whipped cream and a sprinkle of cinnamon.