In a medium bowl, add the berries, sugar, and a pinch of salt and stir to coat. Let sit for at least 20 minutes.
Place a fine mesh sieve over a bowl and pour the fruit into the sieve. Stir the fruit around and gently press to drain off any liquid. Save that liquid for topping.
In a large bowl, add the heavy cream and use an electric beater to beat on high until stiff peaks form (about 2-4 minutes). Add in the yogurt and beat until combined and fluffy (just about 30 seconds). Fold the cookies into the whipped yogurt, then fold in the drained fruit. Let the mixture sit in the fridge for at least 2 hours or overnight.
Serve topped with reserved juices and more cookie crumbles.