Heat oven to 350°F. Line 2 (9-inch) round cake pans with foil so edges extend over sides of pans. Cut cookie dough in half. In bottom of each pan, press half of dough. Sprinkle each cookie layer with 1 tablespoon sugar. Bake about 20 minutes or until light golden brown. Cool in pans on cooling racks 10 minutes.
Use foil to lift cookie layers from pans; place on cooling racks. Cool completely, about 20 minutes.
In small bowl, beat pudding mix and milk with wire whisk about 2 minutes or until thickened. In another small bowl, beat whipping cream with electric mixer on high speed until stiff peaks form. Fold whipped cream into pudding mixture. Reserve 1/2 cup mixture for garnish.
Remove foil from cookie layers. Place 1 layer on serving plate. Spread with half of pudding mixture; top with half of the sliced strawberries. Place second cookie layer on strawberries; top with remaining pudding mixture and sliced strawberries.
Spoon reserved pudding mixture onto center of shortcake. Arrange whole strawberries on top. Refrigerate at least 1 hour before serving. Cut into wedges.