Beat room-temperature cream cheese in a large bowl or stand mixer until fluffy and completely smooth.
Add powdered sugar and vanilla extract; beat until combined.
With mixer running, slowly pour in cold heavy cream. Increase speed and beat to stiff peaks.
Spread a thin layer of filling across the bottom of a 9x13-inch dish.
Lay graham crackers in a single layer, breaking pieces to fill edges.
Spread one-third of the remaining filling evenly over the cracker layer.
Add another layer of graham crackers, then another third of filling.
Repeat: crackers, then remaining filling on top. You will have 3 cracker layers and 4 cream layers total.
Cover tightly with plastic wrap. Refrigerate at least 6 hours or overnight.
Add toppings just before serving. Slice into squares with a sharp knife, wiping blade between cuts.