For the pot pie: Sprinkle the pork with salt and pepper. Heat the olive oil in a large Dutch oven over medium-high heat. Working in batches, brown the pork on all sides. Remove to a plate and set aside.
To the Dutch oven--with the brown bits still in the pot--add the onions, garlic and oregano; cook, stirring, until fragrant, 2 to 3 minutes. Stir in the flour until completely combined into a roux. Pour in the cognac and simmer until reduced by half. Add the chicken broth and cream, and stir to combine. Add the browned pork. Bring to a simmer, partially cover the pot, and braise over medium heat until the pork is just fork tender, 1 1/2 hours. Stir in the kale, carrots and potatoes, cover, and cook over medium-low heat for another 15 minutes.
For the biscuit topping: Preheat the oven to 400 degrees F.
In a large bowl, whisk to combine the flour, cornmeal, baking powder and sugar. Add the milk and the egg, stirring until just combined. Stir in the Monterey Jack and the melted butter; stir until a batter consistency is reached.
Spoon tablespoon-size balls of the batter over the pot pie until the top is fully covered with biscuit balls. Brush the tops of the biscuits with milk.
Bake until the biscuit topping is golden and cooked through, 15 minutes.