Preheat the oven to 375°F (190°C).
Prepare the stuffing by heating olive oil in a skillet over medium heat. Sauté the chopped onion and celery until softened, about 5–7 minutes.
In a large bowl, combine the sautéed vegetables with bread crumbs, cranberries, sage, chicken broth, cream cheese, salt, and pepper. Mix well to combine.
Lay the turkey breast skin-side down on a clean surface and gently pound it to an even thickness, about 1 inch.
Spread the stuffing evenly over the turkey, leaving a small border around the edges.
Roll the turkey breast tightly from one side to the other, tucking in the stuffing as you go.
Secure the roulade with kitchen twine at 1-inch intervals.
Season the outside of the roulade with additional salt and pepper.
Transfer the roulade to a roasting pan and roast for 60–75 minutes, or until the internal temperature reaches 165°F (74°C).
Remove the roulade from the oven and let it rest for at least 10 minutes before slicing.
Slice the roulade into rounds and serve with your favorite sides.