Preheat oven to 400ºF and line a sheet pan with parchment paper. Add the butternut squash to a mixing bowl and drizzle with 1 tbsp olive oil. Sprinkle with ½ tsp salt and ¼ tsp black pepper and toss to combine. Arrange the squash on the prepared baking sheet in one even layer, and bake for 18-20 minutes flipping halfway through, or until golden brown and completely tender. Remove from the oven and allow to cool.
While the squash bakes, place a large skillet over medium-high heat. When hot, add 1 tsp olive oil and swirl to coat. Arrange the Daring Original Pieces in one even layer, and sear for 5-6 minutes on each side, or until cooked through and golden brown. Remove to a clean plate and allow to cool.
To prepare the vinaigrette, whisk together ¼ cup olive oil, apple cider vinegar, dijon mustard, maple syrup, thyme, ¼ tsp salt ¼ tsp black pepper in a medium bowl until completely combined — 20-30 seconds.
To serve, add the arugula, seared daring, roasted butternut squash, and apples to a large mixing bowl. Drizzle just enough vinaigrette over to moisten the salad, and use tongs to toss together. Serve in large bowls and garnish with pumpkin seeds, if using.