Bring the steak to room temperature (20 minutes). Letting the meat rest at room temperature ensures it cooks evenly; a cold center will overcook the exterior before the interior reaches the desired doneness.

Pat the steak dry with paper towels, then season both sides generously with coarse salt and freshly ground black pepper. Drying the surface and salt early helps form a better crust when searing or grilling because moisture prevents browning.

Preheat a grill or a heavy cast-iron skillet over high heat until smoking hot. High, direct heat is necessary to quickly sear the exterior and develop a deeply flavored crust (the Maillard reaction) while keeping the interior juicy.

Lightly brush the steak with 1 tablespoon of olive oil just before it goes on the grill to promote even browning and prevent sticking. Avoid oiling the grill directly — it can cause flare-ups that char the steak unevenly.

Grill the steak: sear for about 3–4 minutes per side for medium-rare (depending on thickness — skirt is thin and cooks quickly). After the initial sear, move the steak to a cooler part of the grill for 1–2 minutes if it develops too much char. Use an instant-read thermometer: 52–54°C (125–130°F) for medium-rare, 57–60°C (135–140°F) for medium. Quick, hot cooking preserves tenderness and flavor.

Transfer the steak to a cutting board and tent loosely with foil. Rest for 8–10 minutes. Resting lets the meat’s juices redistribute so they don’t run out when you slice — that keeps slices moist and flavorful.

While the steak rests, assemble the salad and dressing. In a medium bowl whisk together the remaining 1 tablespoon olive oil and 1 tablespoon balsamic vinegar; season with a pinch of salt and a generous grind of black pepper. The simple vinaigrette adds tang and balances the oil and brine from the olives; emulsifying briefly helps it cling to the arugula.

Halve or quarter the roasted cherry tomatoes (if large) and thinly slice the roasted red bell pepper into 1-cm ribbons. Combine tomatoes, roasted pepper ribbons and pitted mixed olives in the bowl with the dressing. Toss gently to coat — tossing while the steak rests lets the flavors marry and the tomatoes release a little of their juices to enrich the dressing.

Toss the arugula lightly with a small drizzle of the dressing or a pinch of salt (you want the greens slightly dressed so they don’t wilt under warm steak). Arugula’s peppery bite provides freshness and contrast to the rich meat.

Slice the rested steak thinly across the grain into 3–5 mm slices. Cutting against the grain shortens muscle fibers and yields a tender bite — especially important for skirt or flank steak which has long grain.

To serve, arrange the dressed arugula on a platter or individual plates, mound the roasted tomato-pepper-olive mixture over the greens, then fan the sliced steak on top. Spoon any resting juices on the steak and finish with an extra drizzle of high-quality olive oil and an optional grind of black pepper. The contrast of warm steak over cool peppery greens with briny olives creates balanced texture and flavor.

Optional finishing: scatter a few flakes of flaky sea salt or a squeeze of fresh lemon if you want a brighter finish. Little touches like sea salt flakes enhance the steak’s flavor just before serving.