In a baking dish, add the olive oil, garlic, lemon juice, dijon, coconut aminos, and cayenne and whisk to combine. Set aside.
With a meat mallet or the bottom of a heavy skillet, tenderize the steak by pounding it 30-40 times. Season with salt and pepper.
Place the tenderized steak into the marinade and flip back and forth in the marinade to evenly coat. Cover and let it marinate for 20 minutes at room temperature or up to 24 hours covered in the fridge.
Make the Dressing:
In a small bowl or jar, add the olive oil, lemon juice, dijon, red wine vinegar, shallot, salt and pepper. Whisk to combine.
Cook the Steak:
Heat grill over medium-high heat (375- 400 degrees F) and oil the grill grates (to do this, dip a wadded paper towel in a little oil and, using tongs, wipe the oil evenly over the grate. Be careful not to use too much oil, because that's a sure fire way to start a good flare-up—a little goes a long way here.)
Carefully place the steaks on the hot grill and cook until grill marks appear, about 4-5 minutes per side. The lid should be closed throughout the cooking process.
Remove from the grill and let rest for 10 minutes before slicing and serving.
Assemble the Salad:
Spread the arugula and cherry tomatoes over a large platter and drizzle with the vinaigrette. Slice the steak and add on top of the salad.