Combine first 5 ingredients in a small bowl; rub evenly over both sides of steak.
Heat oil in a large skillet over medium-high heat.
Add steak; cook 3 minutes on each side or until desired degree of doneness.
Let stand 5 minutes; cut steak diagonally across grain into thin slices.
Combine 1 tablespoon cider vinegar, 1 teaspoon Dijon mustard, 1/4 teaspoon salt, and 1/4 teaspoon freshly ground black pepper in a large bowl; stir well with a whisk. Gradually add 2 tablespoons olive oil to vinegar mixture, stirring constantly with a whisk.
Add 6 cups arugula and 1 cup halved cherry tomatoes to dressing in bowl; toss well to coat.
Sprinkle 2 cooked and crumbled bacon slices evenly over salad.