Heat a grill to medium high heat.
Place the pineapple on a skewer then place the jalapenos and pineapple on the grill. Cook for 5 minutes, turning every minute or so. Remove to a plate to cool.
Sprinkle the chicken with the jerk seasoning. Place on the grill and cook for 5 minutes per side or until it is cooked through. Remove to a plate and let rest 5 minutes. Chop into pieces.
Meanwhile, roughly chop the lettuce and divide between two large plates.
Starting at one side of the salad layer the bell pepper, mango, avocado, chicken, bacon, cheese, and tomato onto the salad.
Sprinkle the salad with the scallions then set aside.
Carefully cut the tops off the jalapenos and scoop out the seeds. Put the jalapenos, pineapple, and dressing ingredients into a food processor and process until smooth.
Drizzle the salads with dressing and serve.