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To prepare pork: Combine chipotle and sauce, garlic, orange juice, lime juice, vinegar, oregano, cumin, salt and pepper in a blender or mini food processor; blend or process until the chipotle is chopped and the mixture is relatively smooth. Pour into a sealable plastic bag, add pork and seal, squeezing out any excess air from the bag. Turn to coat with the marinade. Refrigerate at least 1 hour and up to 8 hours.
Preheat grill to high or heat a large indoor grill pan over high heat. Remove the pork from the marinade (discard marinade). Grill the pork, turning occasionally, until an instant-read thermometer inserted diagonally into the center of the meat registers 145°F, 12 to 15 minutes. Transfer the pork to a cutting board and let rest for 5 minutes before slicing.
To prepare salad: With a sharp knife, remove the peel and skin from the orange. Working over a large bowl to catch the juice, cut the segments from their surrounding membrane. (Discard membrane, pith and skin.) Thinly slice the pork and add to the bowl with the orange segments along with fennel, onion, oil, vinegar, salt and pepper; toss to combine. Sprinkle with pepitas.