While waiting for the water to boil, heat a large skillet over medium-low heat. Add the guanciale and cook slowly, stirring occasionally and letting the fat render, until crisp, about 10 minutes. Remove the guanciale with a slotted spoon and set aside on a plate, leaving the fat in the skillet. Add the dried herbs to the skillet and stir until fragrant, about 1 minute. Add the can of tomatoes, smash the whole tomatoes with a wooden spoon, and increase the heat to medium. Cook, stirring occasionally, while you boil the pasta.
Add the pasta to the boiling water and cook 2 minutes less than the package directions. Using tongs, transfer the pasta to the sauce. (Don't worry about shaking off the water beforehand; the water is nice and starchy and will help the dish come together.) Stir the pasta and the sauce together, adding a little pasta water, if needed, to thin the sauce.
Reserve 2 teaspoons of the cooked guanciale. Add the remaining cooked guanciale, half of the pecorino and some pepper. Stir and cook until the pasta is barely tender and the sauce has a nice sheen to it, about 2 minutes. Plate the pasta and garnish with the remaining pecorino and reserved 2 teaspoons of guanciale.