Heat a cast-iron skillet over medium-high heat and add 1 tablespoon of olive oil.
Generously season the flank steak with salt and pepper, then place it in the hot skillet.
Cook for 10–15 minutes, flipping once halfway through, until it reaches your preferred doneness.
Transfer the steak to a cutting board and let it rest for 10 minutes before slicing against the grain.
Meanwhile, make the dressing by blending the remaining olive oil with the lime juice, cilantro, and a pinch of salt and pepper until smooth.
Return the skillet to medium heat and add the bell pepper, red onion, and cherry tomatoes.
Sauté for 3–5 minutes, until they soften and begin to char, then remove from heat.
Divide the chopped romaine among serving plates.
Add the sliced steak, sautéed vegetables, and avocado to each salad.
Finish by drizzling the cilantro lime dressing over the top.