Macerate the strawberries: Toss sliced strawberries with granulated sugar and let sit for 20 minutes until juicy.
Make the cream filling: Beat softened cream cheese with powdered sugar and vanilla until completely smooth. Fold in two thirds of the whipped topping gently until light and airy.
First layer: Spread angel food cake cubes in an even layer across the bottom of the trifle bowl or dish.
Add filling and strawberries: Spoon half the cream cheese mixture over the cake. Top with half the macerated strawberries and their juices.
Repeat layers: Add remaining cake cubes, then remaining cream filling, then remaining strawberries.
Top and chill: Spread the remaining whipped topping across the top. Garnish with whole strawberries. Cover and refrigerate for at least 3 hours before serving.