Combine ingredients for the marinade in a food processor and pulse until smooth. In a small container, coat steak in marinate and set aside for at least an hour or refrigerate overnight.
Heat a medium-sized pan to high with a dash of EVOO and add the steak. Keep in mind, chili will fill the air as the spices may smoke. Cook steak to medium-rare by searing it for 2 minutes on each side. Once cooked, let meat rest for 5 minutes then slice against the grain.
The Dressing & Salad
In a medium bowl, mix together ingredients for the dressing and whisk until the EVOO emulsifies.
Halve your cherry tomatoes and put them in an air-tight container with pepper and apple cider vinegar. Add water until tomatoes are fully covered. Let sit for 6 hours to 2 days. Please note: These will enhance your salad’s flavors, but you can use plain cherry tomatoes too.
Plate by layering lettuces followed by red onion, pickled cherry tomatoes and steak slices. Cover with dressing to taste and top with basil.