In a large bowl, using an electric mixer, beat cream, powdered sugar, and vanilla until medium peaks form.
In a large bowl, add mascarpone and then gently fold in the whipped cream.
In a large glass measuring cup, combine coffee and Grand Marnier.
Let the coffee mixture cool before dipping in the ladyfingers.
Wash and slice the strawberries, about 1/4” thick. You don’t want super thin slices, as you want to see the strawberries in the layers. Place them in a bowl to use for later.
Spread a layer of whipped cream in the bottom of a large trifle dish.
Working one a time, quickly dip 1 ladyfinger into coffee mixture. DO this quickly as the ladyfingers will fall apart fast.
Place the dipped cookie into the trifle dish, over the whipped cream. Continue dipping and placing the ladyfingers in a circle until bottom is completely covered, breaking ladyfingers if you need.
Spread a third of the whipped cream over those ladyfingers.
Then, spread half of the jam over top, gently. Try to get closer to the edges so you can see the strawberry jam from the outside of the dish. The layers look so pretty.
Layer about 13 sliced strawberries over the jam.
Repeat with a second layer of ladyfingers. whipped, cream, jam, and strawberries.
Add a third layer of dipped ladyfingers, then top with remaining whipped cream.
Add fresh strawberries to the top.
Cover with plastic wrap and refrigerate until well chilled, at least 2 hours.