Prepare the pound cake. Cut the pound cake into approximately 1-inch cubes
Prepare the strawberries. Wash and thoroughly dry the strawberries. Remove the stems and cut large strawberries in half. Smaller berries can be left whole.
Assemble the skewers. Alternately thread pieces of pound cake and strawberries onto each wooden skewer. Repeat until the skewer is filled, leaving enough room at the bottom to hold comfortably.
Make the Strawberry Balsamic Whipped Cream. Pour the cold heavy whipping cream into a chilled mixing bowl. Beat until it begins to thicken. Add the powdered sugar and vanilla and continue whipping until soft peaks form.
Add Strawberry Balsamic. Gently add 1 tablespoon Strawberry Balsamic Vinegar and continue whipping just until incorporated. Taste and add additional Strawberry Balsamic, if desired. Be careful not to over beat.
Finish the skewers. Arrange the strawberry shortcake skewers on a serving platter. Just before serving, drizzle generously with Strawberry Balsamic Vinegar.
Serve. Place the Strawberry Balsamic Whipped Cream in a bowl alongside the skewers for dipping
Make-Ahead TipThe pound cake can be cubed and the strawberries prepared ahead of time. The whipped cream can also be made several hours in advance and refrigerated. For the prettiest presentation, assemble and drizzle the skewers shortly before serving.
