Start by adding the peeled garlic to your food processor and pulsing until it's finely minced. Toss in the parsley and cilantro next, pulsing again until everything is chopped small and even. Finally, add the oil, lemon juice, oregano, red pepper flakes, and salt, then pulse.
If your flank steak is on the larger side or won't fit your skillet, cut it in half first, making sure to slice with the grain rather than against it at this stage. Place the steak in a baking dish or a resealable bag and pour about a third of the chimichurri over it. Turn the meat to coat it fully in the sauce.
Let the steak sit in the marinade for at least 30 minutes, though I usually try to give it closer to one or two hours if I have the time. This step is what really tenderizes the meat and works the garlic, herbs, and lemon deep into the fibers. Keep it covered in the fridge while it marinates.
Set a cast iron skillet over medium-high heat and let it warm for a few minutes before adding any steak. While it heats, pull the steak from the marinade, scrape off the excess, and pat it completely dry with paper towels. A quick sprinkle of salt right before cooking helps the crust form.
Add a tablespoon or two of oil to the hot skillet, depending on how much steak you're cooking, and wait until it shimmers. Carefully lay the steak in with tongs and let it cook undisturbed for three to four minutes per side, adjusting slightly based on thickness and how you like it.
Move the steak to a cutting board and let it rest for about five minutes so the juices redistribute instead of spilling out when you cut. Slice it thinly against the grain, arrange the pieces on a platter, and spoon the remaining fresh chimichurri generously over the top before serving.