Heat a cast-iron skillet over medium-high heat. Rub the steaks all over with the halved garlic clove. Season the steaks with salt, pepper and the chopped rosemary; drizzle with EVOO. Add to the hot skillet and cook, turning once, for 9 to 10 minutes for medium-rare. Let the meat rest, then thinly slice against the grain.
Meanwhile, using a food processor, pulse the arugula, parsley, sage, shallot, the leaves of the remaining rosemary sprig and the grated garlic clove until finely chopped. Pour in 1/2 cup EVOO, the vinegar, salt and pepper and process into an herb sauce.
Slice the meat. Top with lots of herb sauce and serve with the tomato.