Stir softened cream cheese with chopped olives, dry pepperoncini and oregano until evenly combined.
Spread half the mixture over each tortilla, leaving a 1/2-inch border. Arrange salami and provolone in thin overlapping layers, then lay one dry romaine leaf across each center.
Roll each tortilla tightly into a log without folding the ends inward. Wrap snugly in food wrap and refrigerate for 60 minutes until firm; chilling is included in prep time.
Unwrap and trim about 1/2 inch from each end, reserving the small trimmings for the cook. Cut each log into 6 equal pinwheels with a sharp serrated knife, wiping the blade between cuts.
Pack 3 pinwheels per portion in a rigid container. Keep at 40°F or below and transport with ice packs, serving cold.