Preheat oven to 375 degrees Fahrenheit. Place the ground elk in a large mixing bowl and set aside.
In a medium pan, heat the olive oil over medium heat. Add in the finely chopped carrots, onions, and garlic, and sauté for 5-6 minutes until the veggies begin to soften. Once cooked, add them into the large bowl with the elk.
To the mixture, add the dried thyme, ground sage, salt, black pepper, eggs, breadcrumbs, and chopped parsley.
In a small mixing bowl, add the ketchup, Worcestershire sauce, and brown sugar. Stir to combine. Add half of this ketchup mixture into the elk (save the remaining half to glaze).
With a large wooden spoon, mix the meatloaf until all ingredients are well combined. Divide the meatloaf mixture in two. it will make two loaves. Cover with plastic wrap and chill the meat mixture for at least 1 hour.
In a large cast iron skillet (or on a baking sheet pan covered in parchment paper), place one half of the meatloaf mixture, and form it into a loaf shape, about 1.5 inches high, and 4 inches wide. Make sure it is an even height, as you want the meatloaf to bake through. Repeat with the remaining meat mixture, so you have two loaves on the cast iron skillet or baking sheet.
Using a brush or a spoon, spread the remaining tomato mixture on top of each loaf as a glaze. Bake for 30-40 minutes, or until meatloaf reaches an internal temperature of 140 degrees Fahrenheit (which you can tell with a meat thermometer).
Remove skillet or pan from the oven, and slice. Store leftover meatloaf in an airtight container for up to 3 days.