In the bowl of a stand mixer cream together butter and brown sugar until light and fluffy. Beat in eggs one at a time. Beat in vanilla.
Combine flour, baking soda, cinnamon and salt together in a bowl. Beat into wet mixture. Beat in pumpkin puree and chocolate chips.
Scoop heaping tablespoonfuls of dough onto a cookie sheet 1 inch apart. Bake in preheated oven for 12 minutes.
Remove from oven allow to cool a couple minutes on the cookie sheet. Transfer to a cooling rack to cool completely.
Once cool, make ganache by combining chocolate chips and heavy cream together in a bowl. Microwave for 30 seconds. Stir. If chocolate isn't melting, microwave for another 30 seconds. Stir. Let stand one minute and stir until the mixture becomes glossy.
Dip the cooled cookies into the chocolate ganache. Place on a piece of wax paper until the ganache hardens. Serve.