Place a silpat or parchment paper on the counter. Add the brown sugar, maple syrup, and butter to a small saucepan. Turn heat to medium and stir until melted and bubbly. Add pecans, cook while stirring until sugar crystalizes and adheres, 2-4 minutes. Scrape pecans onto parchment, spread, sprinkle with salt, and cool completely.
For the vinaigrette, add ingredients to an airtight container or small bowl. Shake or whisk to combine and refrigerate for at least 30 minutes.
If steaks are thicker than 1-1/2", preheat oven to 400°F.
Meanwhile, line a plate with paper towels. Add 1/4 cup olive oil to a large (10-12") oven-safe, preferably cast iron skillet over medium-high heat. Once hot, add half the shallots, pan fry until golden brown (NOT dark brown), 2-3 minutes, stirring often with tongs. Transfer to prepared plate, sprinkle with salt. Repeat with remaining shallots. Drain excess oil from skillet and return it over heat just below high.
Place seasoned steaks inside the hot skillet. Sear for 3 minutes. Flip, lower heat slightly, and sear for 2 minutes for rare, 3 minutes for medium-rare, or 4 minutes for medium. Remove steaks to a cutting board, rest for 10 minutes before slicing against the grain.
Divide the lettuce between two plates. Top with sliced steak, candied pecans, fried shallots, dried cherries, and dollops of goat cheese. Drizzle with Maple Balsamic Vinaigrette then serve.