Let cream cheese sit at room temperature for 20-30 minutes until soft enough to press your finger into easily. In a mixing bowl, combine softened cream cheese and powdered sugar. Beat with hand mixer on medium-high speed for 2-3 minutes until fluffy, smooth, and completely lump-free. Color should lighten slightly from ivory to pale cream, and texture should look like thick frosting.

Transfer cheesecake mixture into a piping bag or zip-top bag with one corner snipped off (cut about 1/2 inch from corner). This makes layering neater and prevents smearing on sides of glasses.

Add about 2 tablespoons graham cracker crumbs to bottom of each 8-ounce glass or parfait cup. Use back of spoon to press down gently and create even layer. Pipe layer of cheesecake filling on top of crumbs, filling about one-third of glass (roughly 3-4 tablespoons filling per layer).

Add about 1-2 tablespoons strawberry jam on top of cheesecake layer. Use spoon or skewer to gently swirl jam into cheesecake filling by making 2-3 gentle figure-eight motions, creating ribbon patterns. Don't overmix or you'll lose distinct layers. Repeat layers (crumbs, cheesecake, jam swirl) until you reach top of glass, ending with cheesecake layer.

Cover parfaits with plastic wrap and refrigerate for at least 1 hour, though 2-3 hours is even better. This allows filling to set properly so it holds shape. Right before serving, top each parfait with fresh berries. Berries stay brightest when added at last minute.