Pat your flank steak dry with a paper towel and season with kosher salt and freshly cracked pepper on both sides.
Whisk together 2 tablespoons of olive oil, the Calabrian chilies, Worcestershire sauce, and red wine vinegar. Coat the steak in the marinade and transfer it to a zip-top bag. Marinate at room temperature for 30 minutes.
Heat a cast-iron skillet over medium-high heat. Once the skillet is hot, sear the steak for 2-3 minutes per side without moving (we want that crust!). For medium-rare, the temperature should read between 130-135 on an instant-read thermometer. Transfer the steak to a place and loosely tent with foil. Rest for 10 minutes.
While the steak rests, lower the heat on your cast iron skillet to medium. Add 2 tablespoons of olive oil to the skillet and add the tomatoes and sliced shallot. Cook for 2-3 minutes, stirring frequently, until the tomatoes start to burst. Add the garlic to the skillet and season with salt and pepper. Cook for 2-3 more minutes until the shallots and garlic are soft and the tomatoes are blistered.
Slice steak against the grain and transfer to a serving platter. Sprinkle with flaky sea salt and top with the blistered tomatoes. Top with torn burrata and fresh basil leaves. Serve immediately.