Preheat a grill or cast-iron skillet over medium-high heat until very hot.
Pat the flank steak dry and season both sides evenly with the smoked paprika, sea salt, and black pepper.
Place the steak on the grill and cook for approximately 4-5 minutes per side for medium-rare, or until it reaches your desired doneness.
While the steak is cooking, finely mince the fresh parsley, oregano, and garlic.
In a small mixing bowl, whisk together the minced herbs, garlic, red wine vinegar, red pepper flakes, and extra virgin olive oil to create the chimichurri.
Lightly mist the asparagus spears with oil spray and place them on the grill for 3-4 minutes, turning occasionally until tender and slightly charred.
Remove the steak from the grill and let it rest on a cutting board for at least 5 minutes to lock in the juices.
Thinly slice the steak against the grain and serve immediately topped with the zesty chimichurri and grilled asparagus on the side.