Set oven rack about 6 inches from the heat source and preheat the oven's broiler. Line a baking sheet with aluminum foil.
Spread tomato slices out on baking sheet. Drizzle some olive oil over slices.
Broil in the preheated oven until tender, about 6 minutes. Remove from oven and cool until easily handled, about 5 minutes. Peel skin off slices; discard.
Preheat oven to 375 degrees F (190 degrees C). Line another baking sheet with aluminum foil.
Brush both sides of each tortilla with olive oil and arrange on baking sheet.
Bake in the preheated oven until lightly browned and crispy, about 8 minutes. Remove from oven and let cool, about 5 minutes.
Spread 2 to 3 tablespoons of pesto in a thin layer over each tortilla. Top with mozzarella cheese slices, 8 basil leaves, and some roasted tomato slices.
Bake in the preheated oven until mozzarella cheese is melted, 6 to 8 minutes. Cool slightly, about 2 minutes, before slicing with a pizza cutter.
