1. Preheat oven to 400 degrees. In a bowl combine squash cubes, 1 tablespoon olive oil and sea salt to taste, mixing thoroughly to coat squash with oil. Transfer squash to a rimmed baking sheet and roast for 20-25 minutes, until soft. Remove from oven and let cool.
2. Meanwhile, melt butter in a saucepan over medium heat. Once bubbling, stir in brown sugar, followed by pecans. Sauté pecans, stirring frequently, until coated with mixture, 7-10 minutes. Remove from heat and allow to cool completely.
3. Whisk vinegar, honey, remaining 4 tablespoons olive oil, salt and pepper to taste in a small bowl. Assemble salad: Combine arugula, squash, pecans and cranberries in a large bowl, drizzle dressing over and gently toss.