Sprinkle both sides of the steaks generously with salt and pepper. Heat about two tablespoons of the oil in a large skillet over medium-high heat. Add the steaks in batches and cook until browned on both sides and until desired doneness, about 4-5 minutes per side for medium-rare, depending on thickness. Between batches, add more oil to the pan if needed. Cover steaks with foil while resting.
Lower the heat to medium and add a touch more olive oil to the same skillet if needed to prevent sticking. Add the shallots and cook until slightly softened. Meanwhile, crush the peppercorns with a mortar and pestle, or gently with the back of a sturdy chef's knife, and add to the shallots. Once fragrant, pour in the bourbon and stock to deglaze the pan. Stir in brown sugar and simmer until reduced by half, about 6 minutes. Whisk in cold butter followed by the heavy cream.
Transfer steaks to serving platter. Spoon sauce over filets and serve immediately. Serve extra sauce alongside.
