Halve potatoes, then cut each half into four wedges. Place wedges on prepared baking sheet and toss with 1 Tbsp. olive oil, 1/2 tsp. salt, and 1/4 tsp. pepper. Spread into a single layer and roast until potatoes are tender and golden brown, 20-25 minutes. Potatoes will finish cooking in a later step. While potatoes roast, prepare ingredients.

Stem parsley. Mince stems and finely chop leaves. Mince garlic. Halve tomatoes lengthwise. Pat steaks dry, and season both sides with 1/4 tsp. salt and a pinch of pepper.

Combine parsley leaves and stems, red wine vinegar, garlic (to taste), red pepper flakes (to taste), dried oregano, 2 Tbsp. olive oil, 1 Tbsp. water, and 1/4 tsp. salt in a mixing bowl. Stir together and set aside to allow flavors to marry.

Heat 1 tsp. olive oil in a medium non-stick pan over medium-high heat. Add tomatoes to hot pan, cut side down. Sear until browned, 2 minutes. Remove from pan. After potatoes have roasted 20-25 minutes, add tomatoes to baking sheet, seared side up. Bake until tomatoes are softened, but not mushy, 3-4 minutes. Remove from oven and set aside. Wipe pan clean and reserve.

Return pan used to cook tomatoes to medium-high heat. Add 1 tsp. olive oil and steaks to hot pan. Sear undisturbed until browned, 3-4 minutes. Flip steaks, reduce heat to medium, and cook until steaks reach a minimum internal temperature of 145 degrees, 4-6 minutes. Remove steaks from pan and rest 5 minutes.

Serve potatoes on a plate and place tomatoes next to them. Slice steak into 1/4" slices, if preferred. Serve steak up against potatoes and top with a spoonful of chimichurri. Serve remaining chimichurri on the side for dipping.