First, prepare the cakes. Preheat oven to 350F. Spray two 6" cake pans with baking spray, and set aside.
In a large bowl, whisk together the pumpkin, oil, brown sugar, and milk until combined.
Add in the flour, baking soda, baking powder, salt, pumpkin spice, and vanilla. Mix until the cake batter comes together.
Finally, fold in the chocolate chips.
Divide batter evenly between the two cake pans, and bake for 40-45 minutes, until a toothpick inserted in the center comes out clean. Let cool slightly in the pans, then remove and transfer to a rack to finish cooling off. Cakes must be completely cooled before they can be frosted. I recommend wrapping them in plastic wrap and letting them rest in the fridge overnight for easier frosting and stacking!
When ready to assemble, make the frosting. In the bowl of a stand mixer fitted with the paddle, beat together the shortening and vegan butter until smooth and creamy. Add in the vanilla and pumpkin spice.
Mix in the powdered sugar ½ cup at a time until a thick frosting forms. It is normal to have to add 2-3 tablespoon of milk to get the frosting to the right consistency. You want it to be soft but still hold its shape.
To assemble, first cut the cakes in half diagonally to create 4 cake layers. Place 1 layer down on a cake board or plate, and top with some frosting. Repeat with all.
Be sure to set some frosting aside if you want to use it for decorating the top (or you can make another ½ batch if needed). Use the rest of the frosting to coat the outside of the cake.
Finally, make the ganache. Combine the chocolate chips with 1-2 tablespoon of the nondairy milk in a microwave safe bowl. Heat in 20 second increments, stirring in-between, until chocolate is melted and smooth. Add more non-dairy milk as needed until ganache is smooth, shiny, and thin enough to easily run off a spoon.
Decorate the top as desired with the ganache. I like using a squeeze bottle for easier decorating.
Let the cake chill for 10-15 minutes so the ganache can set, then you can decorate the top with the reserved frosting. I used a 4B tip to make the fluffy dollops. Finish off the cake with desired sprinkles. Enjoy immediately, or refrigerate until ready to serve.