Cook the bacon in a skillet and chop up. Set aside.
Prep the shrimp. Dry the shrimp with paper towels and add salt and pepper. Using the same skillet (with some of the bacon fat still in the skillet), cook the shrimp 2 to 3 minutes on each side. Remove the shrimp and set aside.
While the shrimp is cooking, add the flatbreads to the oven on a foil-lined baking sheet. Heat 4 to 6 minutes on each side (longer if your flatbreads are frozen).
Add tomatoes, arugula, a couple of splashes of vinegar and olive oil as well as salt and pepper to a medium-sized mixing bowl. Toss to combine.
Remove the flatbreads from the oven, spread the pesto on both. Add the tossed arugula and tomatoes on top. Then, add the shrimp and bacon. Serve immediately.