Prep the olives. Roughly chop the Castelvetrano olives into pieces with some texture — not a paste.
Build the base. Pour the olive oil into a shallow bowl or plate. Add the minced garlic and let sit for 5 minutes to gently infuse.
Add heat & olives. Spoon in the Calabrese pepper along with a little oil from the jar. Add the sliced olives and stir gently.
Season & finish. Sprinkle the herb seasoning over the top. Drizzle the balsamic around the edge — don't fully stir it in, let it swirl for contrast. Season with salt and pepper.
Top with Parmesan. Scatter the freshly shredded Parmesan over the top just before serving.
Rest before serving. Let the dip sit for 5–10 minutes at room temperature so the flavors meld together.