Preheat oven to 350ºF.
Using a stand mixer or electric beater, beat butter and sugar until creamy.
Add vanilla extract and pumpkin puree and beat until incorporated.
Sift in pumpkin spice, baking powder, baking soda, and flour and mix until just combined.
Fold in chocolate chips. On a lined, thick-bottomed baking sheet (I use a silpat on an aluminum jelly roll pan) scoop out 1.5 tbsp amounts of dough (roughly 1 inch balls) leaving at least 1 inch of space between the cookies for spread.
Bake for 12 minutes (until edges are slightly browned) and let cool on a wire rack for 1 minute before removing from pan and letting cool completely on the wire rack.