In a large pot of boiling water, add 1 tablespoon oil. Cook tortellini according to package directions until al dente. Drain and transfer to large bowl.
Season cooked tortellini with salt and pepper. Add balsamic vinegar and ¼ cup olive oil and mix to combine. Set aside.
Marinate mozzarella: In a small bowl, add mozzarella balls, Italian seasoning, red pepper flakes, and remaining ¼ cup olive oil. Mix to combine and set aside.
Assemble skewers by layering one piece each mozzarella, salami, roasted red pepper, tortellini, basil, artichoke heart, and green olives.
