In the bowl of a stand mixer or in a large mixing bowl with an electric mixer, whip the coconut cream on high speed until soft peaks form. Add vanilla extract and coconut sugar and continue mixing until firm peaks have formed. Set aside.
In a shaker cup, add enough ice to come to the top. Add coffee and vodka. Shake vigorously for 30-45 seconds.
Pour into a martini glass. Dollop a large scoop of the coconut whipped cream on top. Garnish with some dusted cocoa powder and cinnamon.