Preheat the oven to 350°F. Flatten steak with a rolling pin or meat tenderizer. Season with salt and pepper and set aside.
Thinly slice the peppers into matchsticks and the blanched asparagus into similar lengths, then combine in a bowl. Drizzle with 1 tablespoon olive oil and Worcestershire sauce. Season with salt and pepper and set aside.
In a food processor, combine all of the chimichurri sauce ingredients except the olive oil. Pulse the ingredients until finely chopped. On low speed, slowly drizzle in the olive oil until combined. Set aside.
Cut the flank steak into long strips. Fill the steak with the veggies, tightly roll up, and secure with a toothpick.
In a large oven-safe pan, heat 2 tablespoons olive oil over medium-high heat. Add your steak roll-ups to the pan and sear for 2 minutes on each side.
Place the frying pan in the oven and bake for 8 minutes.
Remove from the oven and set aside to rest for 5 minutes. Serve with chimichurri sauce.