Preheat the oven to 400°. In a large, deep skillet, cook the bacon over moderately high heat, stirring frequently, until crisp, about 5 minutes. Add the carrots, onion, tomatoes and 1/4 cup of the olives and cook until the carrots and onion are lightly browned in spots, about 2 minutes. Add the broth, orange zest and orange juice and season with salt and pepper. Cover and simmer over low heat until the vegetables are tender and the liquid has evaporated, about 8 minutes. Discard the orange zest. Stir in the parsley and keep warm.
Preheat a grill pan. Using a sharp knife, make several deep slits in the steaks. Fill the slits with the remaining 2 tablespoons of olives. Season the steaks with salt and pepper and grill over high heat, turning occasionally, until browned all over, about 10 minutes.
Transfer the grill pan to the oven and roast the steaks for about 10 minutes, until an instant-read thermometer inserted in the centers registers 125° for medium-rare meat. Let the steaks rest for 5 minutes before slicing and serving with the ragout.
The vegetable ragout can be refrigerated overnight.