Bring a large pot of salted water to a boil and cook the penne pasta according to package directions until al dente. Drain and spread the pasta on a sheet pan to cool quickly—this prevents it from clumping and allows you to work on other components. While the pasta cooks, remove the kale stems and chop the leaves into 1/2-inch ribbons, then wash and dry thoroughly (I like to use a salad spinner for this, as moisture will dilute the dressing later).
Preheat your oven to 450°F. In a medium bowl, toss the cubed chicken breast with 2 1/2 tablespoons olive oil, 2 tablespoons balsamic vinegar, dried oregano, salt, and pepper until evenly coated. Spread the chicken on a baking sheet in a single layer and roast for 12-25 minutes depending on cube size, until the internal temperature reaches 165°F—the smaller the pieces, the faster they cook. Let cool slightly before using.
In a glass jar with a tight-fitting lid, combine 1/4 cup olive oil, 3 tablespoons balsamic vinegar, honey, and Dijon mustard. Seal the jar and shake vigorously for 15-20 seconds until the dressing is well emulsified and the honey is fully incorporated. I prefer to make dressing in a jar like this because it's easy to shake and creates a better emulsion than whisking by hand.
In a large bowl, combine the cooled pasta from Step 1, roasted chicken from Step 2, chopped kale, dried cranberries, feta cheese, and sunflower seeds. Pour the vinaigrette from Step 3 over the mixture and toss thoroughly until everything is evenly coated and the kale is lightly massaged by the dressing. Taste and adjust seasoning as needed. Serve immediately or refrigerate until ready to serve.