Preheat oven to 425°F (220°C). Line a baking sheet with parchment paper.
In a large bowl, whisk together flour, sugar, baking powder, and salt.
Cut in the butter until the mixture resembles coarse crumbs.
Stir in milk and vanilla extract until just combined.
Drop dough by spoonfuls onto the prepared baking sheet.
Bake for 12-15 minutes or until golden brown. Let cool.
In a bowl, mix strawberries with 2 tablespoons of sugar. Let sit for 10 minutes.
In another bowl, whip the cream with powdered sugar and vanilla extract until soft peaks form.
Split the shortcakes in half, layer with strawberries and whipped cream. Top with the other half of the shortcake.