Preheat the oven to 375°F. Line a baking sheet with parchment paper.
In the bowl of a stand mixer fitted with a paddle attachment, beat together brown sugar, oil, egg, and vanilla until creamy. Add pumpkin and mix until just combined. Add ½ cup oats and allow to sit while you combine the dry ingredients.
In a separate bowl, whisk together the flour, spices, baking soda, and salt.
Add the dry ingredients to the bowl with the wet mixture and mix on low until just combined. Fold in the oats, pecans, and chocolate chips.
Use a cookie scoop to divide the batter into cookies on the prepared sheet pan. Place a piece of wax or parchment paper on top of the scooped cookie dough and use another sheet pan to flatten the cookies to a 2 ½-inch round.
Bake for 10-12 minutes.
While the cookies are baking, make the icing by combining the ingredients in a bowl until smooth. Cover until ready to use.
Remove the cookies from the oven and transfer them to a wire rack. Drizzle the maple cinnamon icing on top. Enjoy!