Prepare the grill for direct, Very High Heat cooking by fully opening both top and bottom dampers. Preheat for 15 minutes and brush the grill grates clean.
Prepare the grill for direct, Very High Heat cooking (over 550°F), activating the Sear Zone if your grill has one. Preheat for 15 minutes and brush the grill grates clean.
Set the grill to 600°F. Preheat for 15 minutes and brush the grill grates clean.
Whisk all the dressing ingredients together until the sugar is dissolved.
Combine the brown sugar, kosher salt, and black pepper in a small bowl. Coat both sides of the skirt steak with the vegetable oil, then season with the sugar and salt mixture.
Grill the steak until lightly charred on the outside and the internal temperature reaches 115°F for medium-rare, 2–3 minutes per side (see recipe tips).
Remove the steak from the grill and let rest for 5 minutes. This allows the internal temperature to rise slightly.
Combine the lettuce, onion, tomatoes, cucumbers, and herbs in a large bowl. Whisk the dressing again, then toss with about half of it. Divide the salad between four plates and top each with chopped peanuts.
Slice the steak against the grain and top each salad with steak. Drizzle with more dressing or serve it on the side.
Recipe Tips
Want to prep your lettuce ahead of time? Tear it straight into your salad spinner, unwashed. Then wash and spin it right before dinner. The whole spinner can go in the fridge—no extra bowls or plastic wrap needed.