Add the butter and sugar to a stand mixer or to a mixing bowl with a hand mixer Beat until light and fluffy. Mix in the vanilla. Add the eggs and mix until well combined.
To a separate bowl, mix the flour, and salt together. Add ⅓ of the flour to the butter and mix. Repeat with another ⅓. Continue like this until all flour is incorporated, until it resembles large buttery crumbles. Take some dough and squeeze in your hand. If it holds together, it is ready.
Using your hands (coat in flour so dough doesn’t stick), press the dough together until it becomes a ball. Cut the dough in half. (you can refer to the attached video to see the steps).
Place a piece of plastic wrap onto your surface and place half of the dough onto he plastic and flatten (this while help when it comes time to roll it out) and wrap. Repeat with the other half and refrigerate for at least 30 minutes. You can also refrigerate overnight.
Preheat oven to 350°F/176°C.
Place a large piece of baking paper/parchment paper onto your work surface. Dust lightly and spread with your hand. Place the dough on top of the floured paper. Dust the other piece with flour and place flour-side down on dough. Roll out the dough to ¼-inch (6 mm) thick. It will be hard to roll at first, wait a few minutes until it is easier to roll. The dough will become softer and stickier and harder to handle the more it comes to room temperature so roll out as quickly as you can. Once rolled out, refrigerate for a few minutes. This will make the dough easier to cut and handle.
Use a 2 ½-inch/6 cm fluted cookie cutter, dip in flour, then cut out the cookies. Use a thin spatula to remove and place on a parchment covered baking sheet evenly apart. Use a small heart-shaped cutter and cut a heart in the center of half of the cookies. The dough will soften and become sticky as it comes to room temperature, so try and work quickly. You can also refrigerate as needed. Depending on the size of your baking pan, you may need to work in batches. Refrigerate when not using the dough.
Bake 12-15 minutes until they start to turn golden brown on the edges but the tops are still pale. Remove from the oven and allow to cool on the pan for 2 minutes. Transfer to a cooling rack to cool completely.
Once cooled, take a cookie without a heart and spread ¼ teaspoon of jam with more in the center than the edges this way it will rise up through the heart. Top with a heart cut-out cookie.