To prepare the dressing: Whisk together all of the ingredients until emulsified. Set aside.
Preheat oven to 350 degrees.
Prepare the croutons: Slice or tear the bread into 1-inch pieces until you have 4 cups and place on a sheet pan. Toss bread with the 2 tablespoons of olive oil. Arrange in a single layer so the pieces of bread are not on top of one another and toast in the oven for no longer than 15 minutes. They should be crispy on the outside, but still slightly soft inside. Set aside to cool.
To prepare the kale: Transfer the chopped kale to a big salad bowl. Sprinkle a small pinch of sea salt over the kale and massage the leaves with your hands by lightly scrunching big handfuls at a time, until the leaves are darker in colour and fragrant, about 30 seconds.
Final assembly: Add the radicchio, fennel, pear, pomegranate seeds, dried cranberries, shallot, and the bread cubes to the kale and mix all ingredients evenly. Drizzle enough dressing into the bowl to lightly coat the leaves (you might not need all of it), then toss well. Drizzle in extra dressing if the salad seems like it needs it. For best flavour, let the salad rest for 10-20 minutes before serving.