Trim fat from steaks. Sprinkle with salt and pepper. In a large skillet, heat oil over medium-high heat; brown steaks on both sides. Transfer to crockpot. Drain fat from skillet.
Add 1/4 cup water to skillet, bring to boil, scraping up brown bits from bottom of skillet. Stir in ketchup, vinegar, brown sugar, worcestershire sauce and jerk seasoning. Scrape over steaks.
Cover and cook on low until tender, about 3-4 hours.