Preheat oven to 350°F and liberally grease a round 8-inch cake pan. Can also use 9-inch, just reduce cook time by a few minutes.
In a medium sized bowl, whisk together flour, cinnamon, pumpkin pie spice, baking powder, baking soda, and salt. Set aside.
In a large bowl, whisk eggs. Add in sugar and pumpkin and whisk until combined, then whisk in olive oil and vanilla.
Slowly add the dry ingredients to the wet until all combined. Switch over to a spatula when batter thickens, do not overmix.
Fold in 1 cup of chocolate chips, then pour into prepared pan. Top with remaining chocolate chips.
Bake for 32-36 minutes or until toothpick inserted comes out clean. Let cool at least 30 minutes before dusting with powdered sugar and slicing into!
