Place the cherries in a medium bowl. Combine 1/4 cup sugar, kirsch, cinnamon, salt, and vanilla bean seeds in a small bowl, and pour over the cherries. Stir to combine. Let the cherries sit while you make the biscuits.
Put the olive oil in a small bowl and place it in the freezer for 20-30 minutes. Position your oven rack to the center of the oven and preheat to 500. Line a baking sheet with parchment paper.
Whisk together the flours, sugar, baking powder, baking soda, and salt in a large bowl. Make a well in the center of the flour mixture. Combine the buttermilk and the olive oil by gradually beating the olive oil into the buttermilk using a fork. Pour all but 2 tablespoons of the buttermilk mixture into the center of the flour. With a fork, start at the center and gently stir and fold the ingredients together until you have a shaggy dough with some flour remaining at the bottom of the bowl. Slowly add just enough of the remaining buttermilk to gather the dough together. The dough will have lumps and look shaggy.
Transfer the dough to a lightly floured work surface and gently flatten it into a 1/2-1/3 inch rectangle. Fold one half of the dough over the other half, and then gently pat into a rectangle about 3/4 inch thick, using as little flour as possible. Brush any visible flour off the top.
Cut the dough into 6 equal pieces. Place on the baking sheet. Bake the biscuits for 5 minutes.
Meanwhile, make the glaze: add the olive and honey to a small saucepan and briefly warm over low heat, stirring until blended.
Remove the biscuits from the oven and brush with the glaze. Rotate the baking sheet and return the biscuits to the oven. Bake until the tops turn golden brown and the sides have crisped up, 4-5 minutes more. Transfer the biscuits to a wire rack to cool a bit while preparing the cherry sauce.
Make the cherry sauce: Taste a small bit of the cherry juice from the bowl of cherries that has been sitting. If too sour for your liking, add 1-2 more tablespoons of sugar. Place the cherries and all their juices in a strainer, and strain the juice. Place the juice in a small saucepan and cook over medium heat until the juice has thickened and has reduced to half its amount. Remove from the heat and add 1 teaspoon of butter, stirring to combine.
For the whipped cream: Add the cream, sugar, and vanilla to a chilled mixer bowl. Beat on low speed until small bubbles form, about 30 seconds. Increase speed to medium and and continue beating, about 30 seconds. Increase speed to high and continue beating until cream is smooth, thick, and nearly double in volume, and 30 seconds.
To assemble shortcakes: Cut the slightly warm biscuits in half length-wise. Scoop some cherries on one half, along with some of the sauce and whipped cream (recipe follows). Top with the other half and serve.