Preheat oven to 350 degrees F. Line a 9 x 13-inch baking pan with parchment paper, allowing for an overhang on the long sides of the pan. Lightly grease and set aside.
Pumpkin Cheesecake: In the bowl of a stand mixer fitted with paddle attachment, whip cream cream until smooth. Scrape down bowl as needed. Add pumpkin puree and mix until incorporated. Add sugar, flour, and pumpkin spice. Mix together. Then add vanilla and heavy cream. Add eggs and mix until thoroughly combined. Set aside.
Brownies: In a large sauce pot, melt butter over medium heat. Once melted, add sugar. Whisk together and continue to heat until mixture is shiny. Remove from heat and allow to cool slightly.
In a medium bowl, sift together cocoa powder, salt, baking powder, and baking soda. Set aside.
Add dry mixture to pot of melted butter. Stir to combine. Add eggs and whisk to combine. Add flour and fold until incorporated. Fold in chocolate chips until evenly distributed.
Assembly: Take half of chocolate brownie mixture and spread onto prepared baking pan. Spread into an even layer.
Top with half of cheesecake batter. Spread into an even layer over brownie mixture. Spread remaining half of brownie mixture over cheesecake batter.
Dollop remaining cheesecake batter over brownie mixture. Using a mini offset spatula or knife, swirl together the brownie and cheesecake layers.
Bake for 45-50 minutes until the center of the brownie no longer jiggle and the edges of the brownie have slightly pulled away from the pan. Do not overbake, as brownies will dry out.
Let cheesecake swirl brownies cool to room temperature before slicing. For cleaner cuts, allow cheesecake swirl brownies to chill in the fridge before slicing.