Cookie Dough: In a large bowl use an electric mixer on medium-high speed to cream the butter, granulated sugar, light brown sugar and vanilla extract.
Add the pumpkin puree. Mix just until incorporated. Add eggs one at a time beating until fluffy and fully combined.
In a separate medium bowl, use a whisk to sift the flour, pumpkin pie spice, baking powder, baking soda and salt.
With the mixer on medium-low speed, gradually add the flour mixture to the wet ingredients, stopping to scrape the bowl periodically.
Once combined, add the pecans beating slowly to evenly distribute. The batter may be sticky.
Cover the bowl with plastic wrap and refrigerate for around 1-2 hours or just until the dough is chilled and can be easily scooped into balls.
Make the Pumpkin Pie Filling: While the cookie dough chills, make the filling. In a small bowl stir together the of the pumpkin puree, heavy cream, sugar, flour, pumpkin pie spice, salt and egg until fully combined. Cover the bowl with plastic wrap and chill until ready to bake cookies.
Once dough is chilled and can hold its shape while being scooped, it is ready to bake.
Bake: Preheat the oven to 350°F. Line two sheet pans with parchment paper.
Using a small scoop (about 1 1/2 Tablespoon) form cookie dough balls and drop onto the parchment lined baking sheet, at least 2-inches apart.
Use the back of a very small spoon to create a well in the center of each dough ball. Fill the center of each cookie with a small amount of the pumpkin center filling, about 1/2 Tbsp. (Be careful not to overfill)
Bake for about 18-20 minutes or until firm, lightly golden brown and the center is no longer wet.
Remove from the oven and let cool on a baking sheet for 3 minutes then carefully remove to a wire rack to finish cooling.
Serve topped with a dollop of whipped cream or Cool Whip and garnish with a pecan.