In a pot, heat the extra-virgin olive oil over medium. Add the sliced pancetta to the pot and saute until crispy. Remove the cooked pancetta from the pot using a slotted spoon and set it aside.
In the pancetta oil, saute the leeks for a few minutes, until soft. Deglaze the pot with the organic chicken stock. Add the cauliflower, potatoes, bay leaf to the stock and simmer for 15 to 20 minutes, until the veggies are fork-tender. Remove the pot from the heat. Fish out about one cup of cauliflower florets and potatoes and set them aside.
Puree the soup using a hand blender, and then put the cauliflower and potatoes pieces back into the pot. Add the aged Cheddar cheese, sea salt and freshly ground black pepper. Turn the heat down to medium-low and whisk until the cheese is melted.
Serve the soup topped with crispy pancetta and fresh chives.