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Whisk ¼ cup mild jerk seasoning paste and 1 Tbsp. vegetable oil in a medium bowl. Add 2 lb. large shrimp, peeled, deveined, and lightly season with kosher salt and freshly ground pepper; toss to coat. Cover and chill at least 30 minutes and up to 8 hours.
Meanwhile, prepare a grill for medium heat; oil grate. Grill 1 medium pineapple, peeled, cored, sliced into ½"-thick rounds, turning halfway through, until tender and there are deep brown marks on both sides, about 4 minutes. Transfer to a cutting board and let cool slightly.
Cut pineapple into ¼" pieces; place in a large bowl. Add ½ medium red onion, thinly sliced, 1 Persian cucumber, halved, thinly sliced, 1 cup finely chopped cilantro, ⅓ cup fresh lime juice, and 1 tsp. Diamond Crystal or ½ tsp. Morton kosher salt; toss well.
Thread shrimp onto skewers. Cook shrimp on grill until opaque and lightly charred, 3–4 minutes per side.
Spoon pineapple salad onto plates with a slotted spoon, then top with shrimp. Spoon any juices left in bowl over shrimp. To make without a grill: Heat broiler. Spread marinated shrimp out on one side of a rimmed baking sheet (do not skewer); arrange pineapple on other side. Broil, turning halfway through, until shrimp are opaque and pineapple is blistered in spots, about 5 minutes.