Make the macerated strawberries: Slice your strawberries and transfer to a medium sized bowl. Add sugar to the strawberries, and mix together until the sugar dissolves and the strawberries start to let out some of their juices. Cover and refrigerate for minimum 30 minutes to let them soften.Preheat your oven to 400°F. Line a large baking sheet with parchment paper, and set aside. Make your biscuits: In a large bowl, combine flour, baking powder, salt, and sugar. Whisk to combine.
Add your cold, cubed butter to the flour mixture. Using a fork or pastry cutter, cut the butter into the dry ingredients until you get a mixture that resembles coarse breadcrumbs.
Add the buttermilk and mix until you get a rough ball of dough. Turn the biscuit dough onto a lightly floured work surface. Optional (for extra flaky biscuits): Flatten the dough into a rough rectangle and fold in half. Repeat the process of flattening and folding the dough 2 to 3 times to build additional flakes! Using a rolling pin or your hands, roll/flatten the dough into a rectangle that's just under 1/2 an inch thick. Cut biscuits out using a 2-1/2 inch, round biscuit cutter.
Arrange the cut biscuits onto your parchment lined baking sheet, leaving a bit of space for the biscuits to expand. Gather up your dough scraps and repeat the rolling/flattening and cutting process until all the dough is used up.
Bake your biscuits in the center of your preheated 400°F oven for 15 to 20 minutes, or until puffed and golden brown. Cool for at least 10 to 15 minutes before assembling your shortcakes.
Make your whipped cream: In a large bowl, combine heavy cream and powdered sugar. Whip until it reaches stiff peaks.
Assemble the shortcakes: Using a sharp knife, cut the biscuits in half. Layer the shortcakes starting with the biscuit bottom, followed by the whipped cream and macerated strawberries, and the biscuit top. Top with more whipped cream and strawberries.