Heat oven to 400 degrees F (205 degrees C). Line a large baking sheet with parchment paper.
In a small bowl, add the yolks of the Egg (2) and Heavy Cream (1 cup), and whisk to combine. Set aside.
In a large bowl, whisk together All-Purpose Flour (1 3/4 cup), Unsweetened Cocoa Powder (1 cup) (plus 1 Tbsp), Baking Powder (2 1/4 teaspoon), Baking Soda (3/4 teaspoon), Granulated Sugar (1/3 cup) and Kosher Salt (1/2 teaspoon) until thoroughly combined.
Add Unsalted Butter (6 tablespoon) and use your fingers to break into small pea-sized bits and coat in dry ingredients. Stir in Dark Chocolate (2 ounce).
Pour the cream mixture into the butter-flour mixture and use a rubber spatula, followed by your hands, to mix and mash it together into one cohesive dough.
Divide dough into 8, roll each lump into a ball, and dip in Raw Sugar (1/4 cup).
Place balls on prepared baking sheet, 2 inches apart. Bake for 15 to 18 minutes, until set but not hard, rotating once halfway. Let cool completely on tray or on a cooling rack.
About 30 minutes before you’re ready to assemble, gently mash a quarter of the Fresh Strawberry (1.5 pound) in a medium bowl using a fork. Add remaining strawberries, Granulated Sugar (2 tablespoon), and Kosher Salt (1 pinch) and stir gently to mix. Set aside for 20 to 30 minutes to macerate, until very juicy.
In a cold bowl, add the remaining Granulated Sugar (1 tablespoon) to the Whipping Cream (1 cup) Whisk or beat the cream to soft peaks.
Use a serrated knife to gently slice each shortcake. Top the bottoms with whipped cream, spoon macerated strawberries over top, and perch shortcake hats on top. Serve immediately.