Add the heavy cream, sweetened condensed milk, cream cheese, vanilla extract, and strawberry jam to a blender. Blend on low speed until combined, scraping down the sides of the blender if needed.
Distribute the contents of the blender evenly between 12 popsicle molds (more or less depending on the size of your popsicle molds). Pop the filled molds into the freezer and freeze for 8 hours.
Add the Nilla wafers, freeze-dried strawberries, and butter to a food processor. Pulse to make fine crumbs. Transfer the coating to a shallow bowl and set aside.
Take the ice cream bars out of their molds (it can be helpful to run them under hot water for a few seconds to loosen them up) and arrange them on a baking sheet lined with parchment paper. Allow the ice cream bars to thaw for a couple of minutes.
Roll an ice cream bar in the strawberry shortcake coating to, well, coat it in strawberry shortcake coating. Return the ice cream bar to the baking sheet and repeat with the remaining bars. If the coating is having a hard time adhering to the bars, allow them to thaw for a bit longer and then attempt to coat them again.
Return the bars to the freezer for 15 minutes or until ready to serve.