In a small sauté pan over high heat, sauté the kale in 1 tablespoon of oil. Reserve at room temperature.
Preheat oven to 350˚ F. With a meat mallet, pound the chicken to ¼-inch thickness. Season both sides with salt and pepper.
Layer shredded Gouda cheese over the chicken, followed by the sautéed kale, roasted butternut squash and shredded Asiago cheese. Roll tightly and reserve.
In a medium pan over medium-high heat, sear the roulade seam side down. Cook for 2 minutes. Turn the roulade and continue to cook for another 2 minutes. Transfer to the oven and bake for 12 minutes. Remove from oven, add butter and baste the chicken as the butter melts. Return pan to the oven and cook for another 6 minutes or until the breast reaches an internal temperature of 165˚ F.