Preheat oven to 350°F. Grease and lightly flour two cake pans, and set aside.
In the bowl of a stand mixer, combine the cake mix, eggs, and pumpkin puree on medium-low speed until just combined. Then turn the speed up to medium-high and beat for 2 minutes, until light and fluffy. Divide the batter between the prepared cake pans and bake in preheated oven for 25-30 minutes, or until a toothpick inserted in the center comes out clean. Let the cake cool completely.
To make the frosting, beat together the cream cheese, butter, and vanilla in the bowl of a mixer. Add in the powdered sugar, ½ cup at a time, until smooth.
To make cake balls, break up the cake into a large bowl, add in the frosting, and using clean hands, smoosh it together until well-mixed. Using damp hands, form the mixture into 1" balls and place them onto a baking sheet. Repeat with all the cake mixture, and then place the baking sheet in the freezer for 20-30 minutes.
While the cake balls are chilling, melt the candy coating in a saucepan over low heat, until smooth. Add in the vegetable oil, a tablespoon at a time, until the mixture is the thickness of a thin alfredo sauce. Do not try to thin out the coating with milk or water (it'll just make it clumpy). Turn off the burner.
Remove the cake balls from the freezer. Dip one end of a lollipop stick in the candy melts and gently press it into a cake ball. Gently dip the cake pop into the candy coating, and spoon more over top to coat. Place it on wax paper to harden. Repeat with remaining cake balls—you should have just enough candy coating to do all the pops.
For decoration: melt the semisweet chocolate in the microwave. Then, using a spoon, drizzle it on the cake pops and top with sprinkles.
Notes
For the best results, dry the cake pops upright. You can do this by sticking the ends of the lollipop sticks in a thick piece of foam, in a cardboard box with holes poked out, or in an upside down colander (if the holes are big enough).
Store-bought cream cheese frosting will work if you don't feel like making your own.
Run the cake pops or balls through the candy coating twice for the most even coating layer. You'll want to allow them to dry in between coats.