Preheat the oven to 350 degrees. Line a baking sheet with wax paper. Add all ingredients except the coconut oil into a stand mixer bowl and mix on medium low speed until evenly mixed. Stream the oil in and mix until the dough begins to clump together. It will look like grains of sand and small clusters. Use your hands to form the clusters into larger cookie pieces and crumble them onto the wax paper. Bake at 350 for 11-12 minutes. Set aside. These may be made ahead and stored in an airtight container for up to three days. 

Preheat the oven to 375. Grease a 9x13 baking pan with coconut oil and a few sprinkles of flour. Combine all ingredients into a stand mixer bowl. Using the paddle attachment, beat at medium speed until the mixture is smooth. Reduce speed to slow, add the baking powder then slowly add the flour 1/2 cup at a time. Mix until the batter is combine but no longer. It will be very thick. 

Pour the mixture into the pan. Use a spatula to smooth out the top. Bake at 375 for 25-27 minutes. Check for doneness with a toothpick at 25 minutes. Let the cake come to room temperature. If you're in a hurry to assemble your cake, place the pan in the freezer for a few until cool. 

Combine the vegan cream cheese and shortening in a stand mixer bowl and beat on medium high until smooth and creamy. Use a spatula to scrape down the sides and mix for another 15-20 seconds. Low the speed to medium the sprinkle in the powdered sugar 1/2 cup at a time until even. Add the pumpkin pie spice and increase the speed to medium high. Beat for 1 minute. Use immediately or store in the fridge in a closed container for up to three days. 

Combine the milk soak ingredients in a small bowl. Pop the cake out of the pan onto a cutting board. Using a 6 inch pan as a stencil, cut out 2 full circles and 2 half circles from the cake. Line the bottom of the 6 inch spring form pan with parchment paper . Use two large acetate strips to line the ring of the pan, forming a mold. Tape the sheets together to secure the mold in place.  

Use the two cake halves to form your bottom layer, saving the prettier full circles for the more visible layers. Fill in the middle with cake scraps and press the layer down with the back of your hands. Brush 1/2 the milk soak onto the layer. Top with 1/5 of the frosting then sprinkle 1/3 of the cookie pieces onto the frosting. Gently press down with your hands then top with another 1/5 frosting. Layer a full cake circle on top and repeat the process for your second layer, saving the larger prettier cookie pieces for your top layer. Finish with a full circle of cake, 1/5 frosting, and large cookie pieces on top of the cake. 

Cover the cake mold and freeze for six hours or overnight to set the layers. When ready to serve, remove the cake from the mold and let thaw for 2-3 hours before cutting. (It also tastes great frozen!)