To make the vinaigrette, add olive oil, maple syrup, apple cider vinegar, dijon mustard, and salt to a small jar, seal, and shake to combine.
Add 1 tablespoon oil to a skillet over medium heat. Once hot, add the bread cubes and toast, tossing frequently, until golden on all sides. Transfer to a large salad bowl.
Add sliced sliced apples, arugula, goat cheese, cranberries, and chopped pecans to the bowl with the bread.
Pour dressing over the salad, then toss to coat. Let the dressing soak into the bread for 10-15 minutes, then crack pepper over the top and serve.