Pat the pork dry with a paper towel; season with salt and rub all over with the jerk seasoning.
In a large bowl, combine the bell pepper, cucumber, blueberries, shallots, lime juice, honey, chile flakes, and 2 tablespoons oil and toss to coat. Season to taste with salt and pepper. Let stand while you prepare the pork.
In a medium frying pan over medium-high heat, warm 1 tablespoons oil until hot but not smoking. Add the pork and cook, turning frequently, until browned but still faintly pink within, 8 to 10 minutes. Transfer to a cutting board to rest for 5 minutes, then slice crosswise.
While the pork rests, add the baby kale and half the cilantro to the salad and toss to coat. Season to taste with salt and pepper. Top with sliced pork.