Heat grill or broiler. Spread flank steak on a cutting board. In a small bowl, combine Italian seasoning, garlic powder and salt, pepper and cayenne. Coat steak with olive oil and then rub spice mixture into steak. Grill or broil for 6 minutes per side, turning once, for a total of 12 minutes. Transfer to a clean board and let rest 5 minutes.
Meanwhile, in a large bowl, combine baby arugula, bing cherries, and crumbled blue cheese. Toss gently with blue cheese dressing. Slice steak against the grain (starting on a small side), into thin slices. Toss with salad mixture. Serve immediately.