Using a mixer with the whisk attachment, whip the heavy cream, powdered sugar, pudding powder and vanilla extract together on high until you have stiff peaks.
In the bottom of a 9x13 pan, spread a thin layer of whipped cream over the bottom. Add a layer of graham crackers followed by about ½ cup of strawberries, enough that there is an even layer. Top with 1/3 of the remaining whipped cream.
Repeat the layers two more times—graham crackers, whipped cream, and strawberries. You may add additional strawberries sliced as desired on top to make it look just to your liking.
Cover with plastic wrap and chill for 4 hours, or overnight. Serve cold.