Cut the pound cake into nine 3/4-inch slices and spread each slice on one side with raspberry jam, using all the jam. Set aside.
Place a layer of cake, jam side up, in the bottom of a 2 1/2- to 3-quart glass serving bowl, cutting the pieces to fit. Top with a layer of raspberries and orange cream. Repeat the layers of cake, raspberries, and orange cream, ending with a third layer of cake jam side down and raspberries.
Whip the cream in the bowl of an electric mixer fitted with the whisk attachment. When it starts to thicken, add the sugar and vanilla and continue to whip until it forms stiff peaks. Decorate the trifle with whipped cream. The trifle can sit for a while at room temperature.
Heat the oven to 350 degrees. Grease and flour two 8 1/2 x 4 1/2 x 2 1/2-inch loaf pans. Line the bottoms with parchment paper.
Cream the butter and 2 cups of the granulated sugar in the bowl of an electric mixer fitted with the paddle attachment for about 5 minutes, or until light and fluffy. With the mixer on medium speed, beat in the eggs, one at a time, and the orange zest.
In a large bowl, sift together the flour, baking powder, baking soda, and salt. In another bowl, combine 1/4 cup of the orange juice, the buttermilk, and vanilla. Add the flour and buttermilk mixtures alternately to the batter, beginning and ending with the flour. Divide the batter evenly between the pans, smooth the tops, and bake for 45 minutes to 1 hour, until a cake tester comes out clean.
While the cakes bake, cook the remaining 1/2 cup of granulated sugar with the remaining 1/2 cup orange juice in a small saucepan over low heat until the sugar dissolves. When the cakes are done, let them cool for 10 minutes. Take them out of the pans and place them on a baking rack set over a tray. Spoon the orange syrup over the cakes and allow the cakes to cool completely.
To glaze, combine the confectioners' sugar and orange juice in a bowl, mixing with a wire whisk until smooth. Add a few more drops of juice, if necessary, to make it pour easily. Pour over the top of one cake and allow the glaze to dry. Wrap well, and store in the refrigerator.
Combine the milk and orange zest in a medium stainless-steel saucepan over medium heat and bring almost to a boil. Remove from the heat.
Beat the egg yolks and sugar on medium-high speed in the bowl of an electric mixer fitted with the paddle attachment until pale and thick, about 5 minutes. With the mixer on low speed, sprinkle on the cornstarch. Beat on medium-low speed until combined, scraping down the bowl with a rubber spatula.
With the mixer on low speed, slowly pour the hot milk mixture into the egg mixture. Pour the mixture back into the pan. Cook over low heat, stirring constantly, until the mixture thickens, 5 to 7 minutes. (Pay attention because it will thicken and then quickly become orange scrambled eggs!)
Immediately, pour the mixture through a fine sieve into a large bowl. Stir in the vanilla, Grand Marnier, butter, and heavy cream. Place plastic wrap directly on the custard and refrigerate until cold.
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