Preheat oven to 300 degrees F.
Place garlic in a piece of aluminum foil, drizzle with 1 tablespoon olive oil, and wrap up in foil. Bake until soft, about 45 minutes. Allow to cool slightly and squeeze garlic flesh from head into a small bowl.
Place tenderloins on cutting board. Rub the top each tenderloin with 1/2 of the roasted garlic and season generously with kosher salt and freshly ground pepper. Mix herbs together and sprinkle half of the mix over the garlic on each tenderloin. Wrap 6 strips of bacon around each tenderloin and tie in place with kitchen twine.
Increase oven to 375 degrees F.
Heat oil in a medium sauté pan over medium-high heat. Sear the tenderloins until golden brown on all sides. Transfer tenderloins to a medium roasting pan or heavy sheet pan; place in the oven and cook to medium doneness about 10 minutes. Transfer tenderloins to clean cutting board and let stand 10 minutes. Remove twine before slicing.