Unwrap the steak and place the rosemary and crushed garlic on top. Rewrap in butcher paper or plastic wrap and chill overnight.
Bring meat to room temperature. Drizzle meat with olive oil and season liberally with Kosher salt and lots of coarse black pepper.
Heat a grill pan or cast-iron pan to high or prepare an outdoor grill.
Heat 2 tablespoons olive oil in large skillet with a lid over medium-high heat. Add the fennel seed, stir 15-30 seconds then add tomatoes, oregano, chili flakes, salt and pepper. Cover pan with a lid and cook 15-20 minutes until all the tomatoes burst, shaking pan frequently without removing lid. Add balsamic to the sauce and stir in parsley.
Grill meat 12-15 minutes for medium-rare (go 2 minutes less for rare and 3-5 minutes more for medium-well). Let rest 10-15 minutes. Thinly slice the meat against the grain.
Dress greens with lemon juice, salt and olive oil to lightly coat; toss with shaved cheese.
Serve sliced steak with sauce spooned across the top and greens alongside.