Place the halved potatoes in a large bowl and drizzle with olive oil.
Season the potatoes with the powdered ranch dressing and black pepper, tossing to evenly coat.
Transfer the seasoned potatoes to the prepared baking sheet, spreading out in an even layer.
Place the baking sheet in the oven and bake for 30 minutes or until the potatoes are golden and tender. Remove from the oven and set aside to cool at room temperature.
Once the potatoes have cooled, place cream cheese, mayonnaise, and mustard in a large bowl. Vigorously whisk to combine the salad base until smooth and creamy.
Add the roasted potatoes, pickled jalapeños, fresh jalapeños, parsley, red onion, scallions, bacon, and cheddar to the bowl.
Stir until the potatoes are thoroughly coated and combined, then cover and refrigerate until chilled, about 30 minutes.