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Season both sides of the steak with salt and black pepper and let it rest room temperature 30 minutes, while you prepare the rest.
Make the Chimichurri Dressing: In a food processor, combine the parsley, garlic, red wine vinegar, lemon juice, red pepper flakes, salt, and pepper. Pulse until finely chopped. With the processor running, slowly drizzle in the olive oil until the sauce is smooth but still slightly chunky.
Preheat a grill, grill pan or cast iron skillet over medium-high heat. When hot, spray with oil and grill the steaks about 5 to 6 minutes per side for medium-rare or until your desired doneness is reached (internal temp of 125F-130F). Transfer the steak to a cutting board and let it rest 5 minutes before slicing thinly against the grain or cutting into cubes.
While it rests, in a large bowl, combine the cucumbers, cherry tomatoes, avocado, red onion and salt. Add half of the chimichurri and toss.
Toss the steak with the salad, adding the remaining chimichurri.
Divide the steak and salad among four plates and serve.