Butterfly the tenderloins by making a 1-inch-deep incision down the length of each without cutting all the way through. Open the tenderloins like books so they lie flat, cover with plastic wrap and pound with the flat side of a meat mallet until they're about 1/4 inch thick.
Sprinkle with salt and pepper. Spread the cream cheese, broccoli, and shredded cheese over the 2 tenderloins, leaving a 1-inch border around all the sides except the long one closest to you. Tightly roll up each tenderloin. Tie each tenderloin with butcher's twine tightly on each end and at 2-inch intervals in between. Brush with oil, and sprinkle with salt and pepper.
Heat an outdoor grill to medium-high heat. Oil the grill grates. Grill the tenderloins over direct heat, turning about every 6-8 minutes to sear the outsides of the meat until all sides are well marked. Move them to indirect heat, cover and cook until a thermometer inserted in the center of each roulade registers 145 degrees F, about 15 minutes more. Transfer them to a cutting board to rest 10 minutes.
While the tenderloins are resting, make the cherry tomato garnish. Make a foil packet and fill with cherry tomatoes, spinach, garlic, olive oil, salt, and pepper. Place foil packet on a medium-heat grill for about 5-7 minutes, or until the tomatoes have burst and the spinach is wilted.
Cut the strings off the tenderloins with scissors, and slice. Serve with the tomato and spinach garnish.