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Coat a 12-inch cast iron skillet with cooking spray.
Arrange pepperoni slices across the bottom of the skillet, allowing them to overlap slightly.
Scatter a layer of shredded mozzarella over the pepperoni, then sprinkle with Italian seasoning.
Spread the marinara sauce evenly over the cheese.
Layer the Colby Jack slices on top, followed by the remaining shredded mozzarella.
Unroll the pizza dough and gently stretch it to fit over the skillet. Tuck any extra dough down along the inside edges of the pan to create a thicker, raised crust.
Brush the surface of the dough with a thin coating of olive oil.
Transfer the skillet to a 400°F oven and bake for 20–25 minutes, or until the dough is fully cooked and the crust turns golden brown.
Take the skillet out of the oven and cover it with a large plate or cutting board. Holding the plate securely against the skillet, carefully turn both over together in one steady motion.
Gently remove the skillet to reveal the pizza. Cut into slices and serve!