½ cup extra-virgin olive oil
3½ tablespoons dried Jamaican jerk seasoning
1½ tablespoons balsamic vinegar
4 small bay leaves, crumbled finely
3 large garlic cloves, minced
2 2¾–3 lb (thick-end) beef tenderloin roasts
Whisk first 5 ingredients in bowl. Pierce tenderloins all over with fork. Place tenderloins in large resealable plastic bag; add marinade and seal. Turn bag to distribute marinade evenly. Chill at least 8 hours and up to 1 day, turning bag occasionally.
Preheat oven to 400°F. Remove beef from marinade; pat dry. Place on rimmed baking sheet. Sprinkle generously with salt and pepper. Roast until thermometer inserted into each tenderloin registers 125°F for medium-rare, about 40 minutes. Remove from oven; let stand 10 minutes. Cut beef crosswise into 1/2-inch-thick slices.