Preheat oven to 350°F (175°C). Line two 9-inch round cake pans with parchment paper. Grease (or butter and flour) the paper.
Whisk together the flour, sugar, ground strawberries, baking powder, and salt.
Add the butter, and mix with an electric mixer on medium-low speed. The mixture will appear sandy.
Combine the milk and vanilla. Add to the batter, and mix on low speed for about a minute.
Add one egg and mix, beginning on low speed and increasing to medium speed after a few seconds. Mix just until combined (about 30 seconds). Repeat with the remaining eggs.
Stir in the jam, mixing just until combined.
Divide the batter evenly between the prepared pans and spread evenly. Lightly tap the pans on the counter a few times to get rid of any large air pockets.
Bake 40 to 45 minutes, or until the cake is golden brown and a pick inserted into the center comes out clean.
Place the cake pans on a wire rack, and allow the cakes to cool completely.
To make the topping:
Place the cookies and strawberries in a food processor, and pulse until broken into large crumbs. (I break the cookies into a few pieces as I put them in the food processor to minimize mixing so that the strawberries aren’t completely powder after mixing.)
Transfer the mixture to a mixing bowl. Add the melted butter, and stir to combine. Alternatively, you can drizzle the butter over the mixture in the bowl of the food processor and pulse to mix.
Spread the topping mixture in a single layer on a lined half sheet pan and allow to dry for about 15 minutes.
To make the frosting:
Using an electric mixer on medium speed, beat the cream cheese, butter, and vanilla until light and fluffy.
Add the confectioners' sugar about a cup at a time, mixing until the frosting reaches the desired consistency and sweetness.
Place one cooled cake layer on a serving plate, and frost the top. Place the other cake layer on top, and finish frosting the top and sides of the cake. Cover the top and about a third to halfway up the sides of the cake with the strawberry/cookie topping. (It’s fine if you don’t use all of the topping.)
Notes
Store tightly covered in the refrigerator up to 4 days.