Add 2 tablespoons of olive oil to a cast iron skillet.

Heat the skillet over medium high heat. When hot, add the tenderloin and sear it on all sides until it's nice and browned.

Carefully transfer the skillet to a 425 degree oven, and cook for 15-20 minutes-- or until the internal temp reaches 145 degrees.

Let the pork rest for a minute or two. Use two forks to 'pull' the meat apart and add it into a large bowl.

Add the corn, chiles, avocado, and paprika to the bowl. Gently stir until everything's evenly incorporated into one mixture.

Spread about 1/4 cup of cheese evenly out over half of a tortilla. Top with a 1/5 of the meat mixture. Sprinkle another 1/4 cup of cheese evenly out overtop of the meat mixture. Fold the tortilla closed.

Heat a large skillet over medium heat. When the skillet is hot, spray it with non stick cooking spray and carefully transfer the prepared quesadilla to it.

Let the quesadilla cook until browned and crispy on one side, about 3 minutes, careful to avoid overcooking/burning. Use two spatulas to carefully flip the tortilla to the other side, and again allow it to cook for about 3 minutes, or again until the cheese has melted and the tortilla's browned and crispy.

Remove the cooked quesadilla to a cutting board. Let it rest for a minute, and then use a pizza cutter to slice it into 3-4 wedges before serving.

In a small bowl whisk together the ranch and chipotle powder until evenly incorporated.

Refrigerate the dressing until ready to use.

Serve with the cooked quesadillas, for dipping.