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Preheat oven to 400°F. Line a rimmed baking sheet with parchment paper or a silicone baking mat; lightly oil.
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Remove the flesh from the baked sweet potatoes. Measure out 1 packed cup. (Reserve any remaining sweet potato for another use.) Place the potatoes in a large mixing bowl and mash well.
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Add the almond meal, egg, cheese (if using), baking soda, dried Italian herbs, garlic, and sea salt. Mix until well-combined. The dough will be fairly damp. Bring the dough together into a ball. Transfer to the baking sheet. Oil your hands and press out into a 9- to 10-inch or slightly larger round that is about 1/2-inch thick.
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Bake for 20-25 minutes.
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Remove the crust from the oven and spread the pesto over the top. Top with the cheese, followed by the thinly sliced fennel and shallots, and halved grape tomatoes.
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Bake for an additional 10-15 minutes, or until cheese is golden and bubbly and the crust is browned to your liking (we like ours pretty dark and crisp!). Remove from oven. Let cool for a few minutes, top with baby arugula, if using, and cut into wedges and serve.