Beat the heavy cream and 1/4 cup chocolate syrup in a bowl with a mixer on medium-high speed until soft peaks form, about 3 minutes. Refrigerate until ready to use. Hull and chop all but 6 strawberries and toss them with the sugar in a separate bowl; set aside.
Melt the chocolate in a microwave-safe bowl on medium-high power in 30-second intervals, stirring, until smooth, about 2 minutes. Dip the 6 whole berries in the chocolate, then transfer to a sheet of parchment paper and let cool.
Heat 2 tablespoons butter in a large nonstick skillet over medium heat. Add the pound cake slices and cook until golden brown, 2 to 3 minutes per side; transfer to a plate. Wipe out the skillet and melt the remaining 1 tablespoon butter. Add the chopped strawberries and 1 tablespoon water and cook until juicy, about 2 minutes.
Drizzle some chocolate syrup on each plate; top each with a piece of pound cake. Top with some of the chopped strawberries and their juices, a dollop of the chocolate whipped cream and a chocolate-covered strawberry.