Slice the loaf in half to make two smaller loaves. Slice one of the smaller loaves in half lengthwise. Then, slice each of those pieces in half lengthwise. Line up the sliced pieces and make cuts about 1 inch apart along the short side. Repeat with the other half of the loaf.**
Arrange half of the pound cake slices in an even layer in the bottom of a 2 & 1/2-quart serving dish.
Mix the liqueur and sugar until the sugar is dissolved. Drizzle half of the mixture over the pound cake in the dish.
To make the filling:
Using an electric mixer on medium speed, beat the cream cheese, sugar, and vanilla until smooth. Add the cream and continue beating until soft peaks form. Gently fold in the chocolate chips.
Spread half of the filling evenly over the pound cake in the serving dish.
Arrange the remaining pound cake slices evenly over the filling. Drizzle with the remaining liqueur mixture.
Spread the remaining filling evenly over the pound cake.
Cover and chill for at least 2 hours or up to 24 hours.
Sift the cocoa powder over the top before serving.
Notes
*I used a basic Sara Lee frozen pound cake. The directions for cutting the cake apply to a loaf-shaped pound cake. If you're using something different, adjust the size of the slices to fit your pan.
**You may need to cut some smaller pieces, depending on the size of your serving dish. Just be sure to make even layers of cake. It doesn't have to be pretty. It just needs to form the layers.