Pound the steak on both sides with a meat tenderizer or pierce with a fork. Transfer to a large resealable plastic bag; add 2 tablespoons olive oil, the lemon juice, 1/2 teaspoon salt and a few grinds of pepper. Seal the bag and shake to coat; marinate in the refrigerator, 2 to 8 hours.
Meanwhile, make the pesto: Toast the pine nuts in a small skillet over medium-high heat, tossing occasionally, until slightly golden, about 3 minutes; let cool. Pulse the parsley, garlic and red pepper flakes in a food processor until almost smooth. Add the toasted pine nuts, cheese and 5 tablespoons olive oil and pulse until combined. Transfer to a bowl and stir in 3 tablespoons water and the olives; season with salt.
Remove the steak from the marinade and pat dry. Bring to room temperature, about 30 minutes.
Heat a large cast-iron or other heavy skillet over medium-high heat; add the remaining 1 tablespoon olive oil, then add the steak and cook until a dark crust forms, about 7 minutes. Turn and cook until a thermometer inserted into the center of the steak (from the side) registers 130 degrees F for medium rare, about 8 more minutes. Transfer to a cutting board and let rest 10 minutes.
Brush the steak with some of the pesto. Thinly slice against the grain and serve with the remaining pesto.
Photograph by Anna Williams
Courtesy of Food Network Magazine