Preheat the oven to 400 degrees F and line a large baking sheet with parchment paper.
In a mixing bowl, combine the ground turkey, pesto, breadcrumbs, egg, 1 cup of the spinach, salt, and pepper. Mix until evenly blended.
Divide the mixture into four equal portions and shape each into a small loaf about 1 inch thick. Place the loaves on the prepared baking sheet.
Scatter the cherry tomatoes and remaining 1 cup of spinach around the loaves on the baking sheet. Drizzle the olive oil over the tomatoes and spinach.
Bake for 25 minutes, or until the internal temperature of the meatloaves reaches 165 degrees F. Let the loaves rest for 5 minutes before serving.