Preheat the oven to 450F.
Line a baking sheet with parchment paper. Add the carrots, olive oil, salt and pepper and toss to coat. Spread out into an even layer and bake for 30-40 minutes or until the carrots are nicely charred and caramelized (you want that charred flavor!).
To make the dressing, in a medium skillet add the olive oil, cumin seeds, and red pepper flakes (if using). Turn the heat to medium-low. Once you start to hear/see the seeds sizzling, continue to cook, stirring often, for about 1 more minute (don’t burn them!). Turn off the heat and stir in the shallot and cinnamon for 30 seconds. Then, immediately add the vinegar, maple, mustard, and salt and stir/whisk vigorously to combine.
In a large bowl, add the carrots, radicchio, and dressing and use your hands to toss to coat thoroughly (make sure you scrape out every last bit of that dressing).
Transfer to a large serving platter or shallow salad bowl. Top with nuts, herbs, and black pepper.