Preheat the oven to 350 degrees F. Lightly grease a 9x9 baking dish, add parchment paper and set aside.
Place quartered strawberries in a bowl and sprinkle with ¼ cup sugar. Place in fridge and let fruit “sweat” out juices for about 30 minutes.
To make whipped cream, place your mixing bowl and whisk attachment (or beaters if mixing with a hand mixer) in the freezer for about 10 minutes to chill. Once chilled, remove from the freezer and add heavy whipping cream, powdered sugar, and vanilla to your bowl. Whether using the Kitchen-aid or a hand-mixer, start mixing on low speed then increase to medium-high. Mix until soft peaks form. Refrigerate until ready to use.
In the bowl of a stand mixer, cream together the sugar and butter until light and fluffy. Add egg and vanilla and mix well.
In a small bowl, whisk together flour, baking powder, baking soda and salt.
Slowly add dry ingredients and half and half to the butter mixture, mixing until just combined.
Pour this into the prepared baking dish and spread to make even. Bake for 18-20 minutes or until a toothpick inserted in the middle comes out clean. Let cool.
Once cool, cut into 9 squares. Cut each square in half, then layer 1 half on the shortcake, along with a spoonful of strawberries and whipped cream, and then the second half on top with more strawberries and whipped cream. Serve immediately.