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Arrange a rack in the middle of the oven and turn on the broiler to high. Meanwhile, cook the chicken and vegetables.
Pat the chicken with paper towels, then season both sides of the cutlets with the sage, 1/2 teaspoon of the salt, and pepper.
Heat 2 tablespoons of the oil in a 10-inch or larger cast iron skillet over medium-high heat until shimmering. Add the cutlets in a single layer without crowding the pan, working in batches if needed. Sear the chicken until the bottom is browned, 3 to 4 minutes. Flip the cutlets and continue searing until the other side is browned and the chicken is cooked through, 3 to 4 minutes more. Transfer the cooked cutlets to a plate, tent with aluminum foil, and repeat cooking any remaining pieces.
Reduce the heat to medium and add the remaining 1 tablespoon of oil. Add the potatoes, season with the remaining 1/2 teaspoon salt, stir to coat with the oil, and arrange in a single layer. Cook until the bottoms just start to brown, 3 to 4 minutes. Flip with a spatula and continue cooking until lightly browned and tender, about 3 minutes more. Stir in the spinach and garlic and cook until just wilted, about 2 minutes.
Remove the skillet from the heat. Place the chicken on top of the vegetables in a single layer. Top each cutlet with a slice of prosciutto, then sprinkle with the cheese. Broil until the cheese is melted and bubbling, about 1 minute.