Gently mix beef, breadcrumbs, 1 tablespoon shallot, 1/2 teaspoon Italian seasoning, garlic powder and 1/4 teaspoon pepper in a large bowl until just combined. Divide the mixture into 8 oblong 3-inch portions.
Overlap the two sides of a chard leaf where the stem was removed and place a portion of beef there. Tightly roll the chard around the beef. Place each roll, seam-side down, in a large nonstick skillet. Pour in broth, cover and bring to a boil over high heat. Reduce heat to a simmer; cook until an instant-read thermometer inserted into the center of a roll reads 165°F, 8 to 10 minutes. Discard any remaining broth.
Meanwhile, heat oil in a medium saucepan over medium heat. Add the remaining shallot, 1 teaspoon Italian seasoning, 1/4 teaspoon pepper and crushed red pepper. Cook, stirring often, until the shallot is soft, 1 to 2 minutes. Stir in tomatoes and cook, stirring occasionally, until slightly reduced and thickened, about 8 minutes. Serve the chard rolls topped with sauce and Parmesan cheese, if desired.