Prepare the strawberry puree. Place strawberries, sugar, vanilla and sherry (optional) into a food processor or blender. Pulse into fine puree. Pour into a large bowl and set aside.
Prepare the cake. I used Angel Food cake but any type of plain, white cake will work. Simply cube the cake into 1x1-inch pieces.
Prepare the filling. Use a package of instant vanilla pudding that's enough for 6 servings (check back of box for information). I used Instant Jello Vanilla Pudding in 5.1oz size package. Prepare the pudding according to package instructions.
Once pudding is prepared, add the cream cheese and whisk the pudding and cheese together using mixer until smooth. If clumps form, keep whisking! Gently fold in the thawed Cool Whip. I placed mine into the refrigerator the night before to thaw.
Assemble the dessert. Using tongs, drop each cake cube into the prepared strawberry puree and turn to coat well. Arrange the cake cubes on the bottom of a trifle dish or glass bowl. Add a layer of the filling, followed by a generous amount of chopped strawberries. If desired, add a ring of sliced strawberries around the edge of the bowl for garnish.
Repeat the same layers again until the bowl is filled. Garnish top with more strawberries.
Dessert can be served immediately or refrigerated overnight.