In a small bowl, stir the graham cracker crumbs and melted butter together until the mixture looks like wet sand.
Spoon about 2 tablespoons of the crumb mixture into the bottom of each of 8 small clear cups and press down lightly with a spoon.
In a large bowl, beat the cream cheese, sugar and vanilla together until smooth with no lumps, about 2 minutes.
In a separate bowl, whip the cold heavy cream with a mixer until soft peaks form, about 2 minutes.
Fold the whipped cream into the cream cheese mixture in two additions, folding gently until no streaks remain and the filling holds a slow ribbon when dropped from the spoon.
In a small bowl, stir the diced strawberries with the jam until coated.
Spoon the cream cheese filling over the crumb layer in each cup, then top with a spoonful of the jammy strawberries.
Cover the cups and refrigerate for at least 2 hours, until the filling is cold and set firm enough to hold its shape when the cup is tilted.
Good to Know
Make these the night before; the crumb layer actually holds its crunch better after a full day chilled than it does after two hours.