Beat the softened cream cheese on low speed until smooth.
Add the light brown sugar and mix for about 30 seconds until fully incorporated.
Next, add in the pumpkin pie spice and mix until combined.
Then, add the vanilla extract.
Next, mix in the marshmallow creme.
With the mixer on low speed, add in the pumpkin puree and mix until combined.
Last, add the Cool Whip.
Spread the dip out on a circular plate or platter.
To make the Jack o'lantern face, start with the triangle in the center to make the nose. Use four chocolate chips for the bottom of the triangle. Work your way up the triangle adding one less chocolate chip on each row.
Next, make the mouth. Place chocolate chips on each side at the top where you want the mouth to start and work your way down and towards the center to form the bottom of the mouth.
Then place chocolate chips to make the center of the mouth. Make a square of four rows with four chocolate chips in each row. Continue making the mouth with the chocolate chips, leaving an empty space on each side of this center square.
Add two triangles for the eyes as you did for the nose.
Finish it off by adding a bundle of chocolate chips at the top for the stem.
Refrigerate for at least 30 minutes before serving.
Notes
We like to pop the chocolate chips on the dip just before putting in the fridge. This way, the dip will firm up and the chocolate chips will not sink. You can even chill the dip first and then put the chocolate chips on top.