Preheat the oven to 375F. Line 2 sheet trays with parchment paper.
With an electric mixer fitted with a paddle, beat together the butter, oil, sugar, syrup, baking powder, baking soda, salt, and pumpkin spice until smooth. Scrape the bowl and then beat in the eggs, one at a time. Continue to beat until the mixture is light & fluffy.
Stir in the pumpkin puree. Add the flour in two additions, making sure to scrape the bowl between each one.
Scoop ¼ cup of batter and place it onto the prepared sheet trays. Repeat, leaving 2” in between each scoop. Bake for 15-18 minutes. Cool on the sheet tray for 5 minutes and then remove them to a wire rack to finish cooling.
For the filling, beat the cream cheese and butter until smooth and fluffy. Add the sugar in two additions. Stir in the vanilla.
To finish, add 2 tbsp of filling to one cookie and top with another. Repeat with remaining cookies.