Place chocolate in a heatproof bowl. Place vanilla and 1 cups cream in a small saucepan over medium heat for 4 minutes or until mixture just starts to simmer. Pour over chocolate. Add a pinch of salt and stir until chocolate has melted.
Cover bowl and refrigerate for 2 hours or until completely chilled.
Using an electric mixer with a whisk attachment, whisk remaining cream until firm peaks just start to form. In a separate bowl, whisk chocolate mixture until just firm peaks form (don’t over whisk).
Reserve 6 cookies, then process remainder in a food processor until fine crumbs form. Layer 10 x 1/3-cup capacity glasses with a little of the chocolate mixture, cookie crumbs and whipped cream. Repeat layering twice more. Roughly chop reserved cookies. Top each glass with chopped cookies and serve.