Preheat the oven to 400 degrees F, and lightly grease a baking dish big enough to fit the desired number of servings without overlapping.
Place the chicken in the baking dish, lightly sprinkle both sides with salt and pepper, and then evenly spread the pesto over the top of each chicken breast. (I use about 1 tablespoon per breast, a bit more if it’s large. I typically spread the pesto on the top of the chicken only, but for more pesto flavor, you may spread some over the bottom of the breast, too.)
For boneless, skinless chicken breasts, bake for 17-20 minutes or until chicken is just about cooked through the center. Remove from the oven, top with tomatoes and cheese, and then bake for an additional 3-4 minutes or until cheese is melted and the chicken is just cooked through. For chicken cutlets, bake for 10-12 minutes, and then continue as directed for regular boneless, skinless breasts. With either, check a few minutes early and add a few minutes as needed to account for oven and varying size chicken breasts.