Combine mayonnaise, sour cream, pickled jalapeno juice, minced pickled jalapenos, garlic, cumin, smoked paprika, cayenne powder, salt, and pepper in a bowl and stir until smooth. Adjust seasoning to your liking.
Shred the rotisserie chicken using forks or your hands, then mix the chicken with a portion or all of the jalapeño sauce until it’s evenly coated and creamy. Keep extra sauce aside for dipping if you want.
Heat a skillet over medium heat and lay down one flour tortilla. Sprinkle a layer of cheese, spread some chicken mixture over it, add more cheese, and top with another tortilla.
Cook until the bottom tortilla turns golden, about 1 minute, then carefully flip and cook the other side until golden as well, roughly 30 to 60 seconds.
Repeat with the rest of the tortillas and filling, then slice each quesadilla into wedges before serving. Serve immediately and enjoy the cheesy goodness!