Using a stand mixer (or hand mixer + small bowl), blend together heavy whipping cream, vanilla extract, and powdered sugar on high until stiff peaks form, about 5-7 minutes. Set whipped cream aside.
In a fresh bowl, using a stand mixer (or hand mixer + small bowl), blend together cream cheese and cocoa powder until mostly smooth, about 1-2 minutes. It’s okay if it’s a little clumpy – just blend until cocoa powder is mostly absorbed.
Drop mixer speed to slow and slowly add whipped cream to chocolate mixture, about 1/3 cup at a time. Mix until smooth and fluffy.
Turn off mixer and add Heath toffee bits. Use a spatula to gently mix together.
Add Christmas Crack dip to a serving bowl of your choice. If desired, decorate top with more Heath toffee bits and sprinkles. Serve dip immediately with saltine crackers.