Shake together vinaigrette and set aside.
Cook barley according to package directions and set aside.
Heat oven to 425°F. Line a baking sheet with parchment. Toss the butternut squash with olive oil and sprinkle generously with salt and pepper.
Arrange on the baking sheet and roast for 10 minutes. Toss and roast for 10-15 more minutes, until soft. Allow to cool completely.
Assemble the jar salads: Add 1.5 tablespoons of dressing in the bottom of the jar. Add in the following order: chickpeas, barley, butternut squash, feta cheese, cranberries and pecans.
Store in sealed containers in the fridge for up to 4 days.
To serve: Shake jar contents out into a bowl. Toss completely in vinaigrette and enjoy!