Melt chocolate at 50% power in the microwave until smooth. Let cool for 5 minutes.
Beat cream cheese and sugar together using a standing electric mixer (with the whisk attachment) or electric hand mixer. Mix in the melted chocolate, scraping the sides of the bowl down as needed. Slowly pour in the whipping cream while mixing. Beat until stiff peaks. Cover and place in the fridge.
When ready to assemble the trifles, place in a piping bag with a large piping tip.
For the Brownie:
Preheat oven to 350 degrees F. Line an 8x8 inch baking dish with foil and then lightly coat with cooking spray.
In a mixing bowl, whisk sugar and cocoa together. Mix in the melted butter, vanilla, and salt. Beat in the eggs and then mix in the flour until just combined and then stir in the chocolate chips. Pour batter into the pan and bake for 25-28 minutes, until toothpick come out clean.
Cool to room temperature before cutting. Cut into half inch cubes.
For Assembling:
Assemble the trifle with a layer of brownie cubes in the bottom of the trifle dishes, pipe on the chocolate cheesecake filling, and drizzle in some chocolate syrup. Repeat layers until you get to the top of the glass.
Serve immediately or place in fridge until ready to serve.