1Heat oven to 350°F (325°F for dark or nonstick pan). Grease bottom only of 13x9-inch pan with shortening or cooking spray. Make brownie batter as directed on box. Spread batter in pan.
2Bake 28 to 30 minutes or until toothpick inserted 2 inches from sides of pan comes out almost clean. Cool completely, about 1 hour.
3Meanwhile, in medium bowl, beat milk and pudding mix with wire whisk until thickened; set aside. In another medium bowl, beat whipping cream with electric mixer on high speed until stiff peaks form. Gently fold whipped cream into pudding mixture until well combined. Cover; refrigerate until serving.
4Cut brownies into 6 rows by 4 rows, making 24 squares. Place 1 brownie square on each of 12 individual dessert plates; top each square with 3 tablespoons pudding mixture. Top each shortcake with another brownie square, 2 more tablespoons of pudding mixture and 2 tablespoons strawberries. Store covered in refrigerator.