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In a deep 12-inch skillet, heat the olive oil over medium. Add the pancetta and cook, stirring occasionally, until it begins to crisp, 4 to 5 minutes. Remove with a slotted spoon and set aside on a paper towel-lined plate.
Add the onion and sliced fennel to the skillet and cook until softened, 3 to 4 minutes. Stir in the garlic, fennel seeds and red-pepper flakes, if using, and cook until the garlic begins to soften and the fennel seeds become aromatic, about 1 minute. Season with salt and pepper. Stir in the crushed tomatoes and their juices. Fill the tomato can halfway with water, swish it around and add that, too.
Bring the mixture to a simmer and cook on medium-low, allowing the flavors to come together, about 15 minutes.
Turn heat back to medium, stir in the shrimp and cook until just pink, 2 to 3 minutes. Add the beans and the cooked pancetta and cook until warmed through, about 2 minutes. Taste and adjust seasonings as necessary.
Divide among bowls, top with the herbs and drizzle with a bit more olive oil, if desired.