Preheat oven to 350 degrees F. Grease two large baking sheets.
Add the light brown sugar and oil to a large bowl. Beat with an electric hand-mixer to combine. Add in the pumpkin, eggs and vanilla extract. Beat well.
In a separate large bowl, whisk together the flour, cinnamon, pumpkin pie spice, salt, baking powder, and baking soda. Fold dry ingredients into the wet ingredients and mix just until combined. Place dough in the fridge for 20 minutes.
Drop chilled dough by 2 heaping tablespoons onto the prepared baking sheets. Bake in the preheated oven for 12 to 14 minutes. Let cookies cool while you make the filling.