Prep the ingredients: Wash and dry all produce. Preheat oven to 450 degrees. Halve the tomatoes. Cut the sweet potato into wedges. Strip the rosemary of the stems and roughly chop the leaves (you’ll want about 1 heaping teaspoon). Smash the garlic cloves with the side of your knife.

Toss the sweet potato wedges on a baking sheet with the smashed garlic, rosemary, a drizzle of olive oil, and a pinch of salt and pepper. Place in the oven for about 20 minutes, flipping halfway through cooking, until golden brown.

Make the vinaigrette: In a small bowl, whisk together the balsamic vinegar, 2 Tablespoons olive oil, and 1/2 teaspoon oregano. Season with salt and pepper. Set aside.

Heat a drizzle of olive oil in a large pan over medium-high heat. Season the steak on all sides with salt and pepper. Add the steak to the pan and cook for 2-3 minutes per side, until browned. Transfer the steak to the baking sheet in the oven to finish cooking for 5-7 minutes, or until cooked to desired doneness. When the steak is done, remove from oven to rest for 5 minutes.

Meanwhile, add the vinaigrette and the tomatoes to the same pan you used for the steak. Let them cook slightly with the residual heat from the pan.

Once the steak tagliata has rested, slice it thinly against the grain. Mound the arugula on a plate and top it with the sliced steak. Serve the rosemary sweet potato wedges to the side and drizzle with the warm tomatoes and vinaigrette and enjoy!