Melt chocolate using a double-boiler (a stainless steel bowl over a saucepan of simmering water) until smooth. Remove from heat while you do the next steps.
Add the cold whipping cream to the bowl of a stand mixer fitted with the whisk attachment. Whisk on high speed until the cream holds a stiff peak. Add the softened cream cheese and beat on medium speed until combined and smooth. Gradually pour in the melted chocolate followed by the vanilla. Finally, add the powdered sugar until it all comes together.
Pipe using a piping bag fitted with a large tip or pour the mixture into 6-ounce ramekins or other small dessert vessels. Top with raspberries, reserving leftover raspberries for serving. Refrigerate until set, about 2 hours.
Serve chilled with additional raspberries on the side.