For the dressing: Whisk all ingredients together in a small bowl. Season with salt and pepper. Store in refrigerator until ready to use.
For the salad: Place steaks in a small ziplock or bowl. Add 2 tablespoons of olive oil and 2 tablespoons balsamic. Refrigerate and let marinate for a few hours or up to overnight.
Remove steaks from fridge and let come to room temperature. Preheat a medium size cast iron pan over medium-high heat. Add remainder of olive oil to the pan. Once pan is hot, season steaks with salt and pepper and add to pan. Cook, turning once, until well seared and cooked to desired doneness (about 3-5 minutes per side depending on thickness of steaks). Remove steaks and let rest, about 5-10 minutes.
Wash and chop romaine, and add to a large bowl or platter. Dress with desired amount of prepared dressing. Top with a large handful of halved cherry tomatoes and shaves of fresh parmesan, to taste.
Once steak has rested, slice thinly against the grain. Add slices on top of salad and serve.
Recipe by Wright Family Table at https://www.wrightfamilytable.com/lighter-caesar-salad-dressing/