In a medium bowl, combine sliced strawberries with sugar and let sit for 10 minutes to macerate.
In a large bowl, beat the heavy cream, powdered sugar, and vanilla extract until stiff peaks form to make whipped cream.
In a trifle dish or large glass bowl, layer 1/3 of the cubed pound cake, 1/3 of the macerated strawberries, and 1/3 of the whipped cream. Repeat the layers two more times.
Top the final layer with a few fresh strawberry slices for garnish.
Refrigerate for at least 30 minutes before serving.