Add cream cheese to a stand mixer with the whisk attachment. Whip until the cream cheese is smooth. Add in heavy cream and whip on high speed until the mixture forms soft peaks. Turn the mixer off add in the powdered sugar then mix for another 30 seconds. Set aside until you are ready to assemble.
Assemble
To assemble the trifle start by adding pound cake into the bottom of the glasses. (I divide it between 4-6 jars depending on size). You can always add this to a large bowl to serve a crowd.
Next layer on cream cheese filling and strawberries evenly to each jar. Repeat.Serve immediately or store in the fridge until ready to serve.
Notes
Don't make too far in advance: These strawberry shortcake trifles are best served immediately, since you don't want the pound cake base to become soggy. If you're looking to save some time and work ahead, you can prepare your pound cake ahead of time then freeze until it's time to assemble the trifle.
Make it boozy: Traditionally, some trifles have been served with sherry, but that generally yields more of an orange flavor. If you're looking to add a little bit of alcohol to your strawberry shortcake trifles, you can experiment with port, rum or brandy.
Store your leftovers: End up with some leftover trifles? You can store them, loosely covered, in the refrigerator. I would recommend eating your leftover trifles within 3 days, as the layers will meld together and the pound cake will become soggy.