Charred Cauliflower with Chimichurri

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Cauliflower:

2 whole cauliflowers

1/3 cup olive oil, plus more for the grill grates

1/2 tablespoon kosher salt

1/2 tablespoon freshly ground black pepper

1 teaspoon paprika

1/2 teaspoon cayenne pepper

Chimichurri:

2 cups fresh parsley

1 cup fresh cilantro

1/2 cup extra-virgin olive oil, or more as needed

1/4 cup red wine vinegar

4 cloves garlic, peeled

1 jalapeño, minced (remove the ribs and seeds for less heat)

1 shallot, quartered

2 teaspoons kosher salt

2 teaspoons freshly ground black pepper