Heat oven to 375°F. Toss bread pieces with the olive oil and season with salt. Spread evenly on a sheet tray and bake for 15-20 minutes or until nicely golden brown and aromatic. Stir the breadcrumbs every 5 minutes while baking, checking for doneness each time. They will continue crisping as they cool, so aim to take them out of the oven before they get too dark.
In a food processor, combine the anchovy fillets, mayonnaise, and garlic. Process until smooth. Slowly add the remaining ingredients (except the salt and pepper), combining fully. Wait until the end to add any salt and pepper as most of the ingredients will add their own salt, and you may not need any.
Dress the croutons with the caesar, and toss to combine well. Let the croutons sit for a few minutes to absorb the dressing. Add the Little Leaf Farms Romaine Leaf and toss gently. Add grated parmesan, toss again. Grind black pepper over top.