Preheat your oven to 400°F (200°C) and line a large baking sheet with parchment paper for easy cleanup.
Prepare the butternut squash by tossing the cubes with 1 tablespoon olive oil, ½ teaspoon salt, and ¼ teaspoon black pepper. Spread in a single layer on half of your baking sheet, leaving room for the chickpeas.
Mix the chipotle seasoning by combining chipotle in adobo, smoked paprika, cumin, garlic powder, ¼ teaspoon salt, and the remaining tablespoon of olive oil in a bowl. Add the dried chickpeas and toss until evenly coated.
Spread the chickpeas on the other half of the baking sheet and roast both chickpeas and squash for 25-30 minutes, stirring halfway through. The squash should be tender and caramelized, and the chickpeas should be crispy.
While everything roasts, prepare the kale by placing it in a large bowl. Add a pinch of salt and massage with your hands for 2-3 minutes until the kale becomes softer and darker in color.
Make the dressing by whisking together tahini, lime juice, maple syrup, minced garlic, salt, and cayenne if using. Add water a tablespoon at a time until you reach a pourable consistency.
Assemble the salad by combining the massaged kale with the roasted butternut squash, chipotle chickpeas, red onion slices, pumpkin seeds, and dried fruit.
Drizzle with the tahini dressing and toss gently to combine. Taste and adjust seasoning if needed.