In the bowl of a stand mixer, combine the butter and brown sugar and beat until creamy. (You can also do this by hand, but it will take a bit more work.)
Add the pumpkin, egg, and vanilla extract and beat until combined. It may look a little curdled at this point - just make sure it is all combined.
In another bowl, combine the flour, oats, cinnamon, baking powder, baking soda, pumpkin pie spice and salt.
Add the dry ingredients to the butter mixture and beat until combined. Add the chocolate chips and fold into the batter.
Drop 2 tablespoons of batter onto a baking sheet lined with parchment paper or a silpat liner, leaving at least 2 inches between each of the cookies.
Bake in the preheated oven until the edges are lightly browned and the middle is still a bit soft, about 8-10 minutes.
Remove from the oven and let them sit on the baking sheet for a couple minutes before removing to a cooling rack to cool completely.
Notes
Nutrition information provided as an estimate only. Various brands and products can change the counts. Any nutritional information should only be used as a general guideline.