Yes — an O-1 itinerary can include several engagements. Whether that worries you or works for you depends on the role you're filling.
An employer who cannot justify a full senior headcount can engage a world-class person fractionally: an advisory block, a project, a retained specialty. The itinerary structure exists for exactly that shape of career — it is how touring and production talent have always worked.
Negotiate it the ordinary way: in your offer, with compensation to match. The visa structure does not prevent a conventional full-time, single-employer arrangement — plenty of O-1 holders work exactly one job. The point is that the floor is flexible, not that the ceiling is.
Treat the first engagement as the cheapest possible trial of a person whose evidence record you have already read. The full-time decision comes later, on your paper.
The O-1 itinerary can span several engagements. Why that's a feature for employers who want senior talent without a full headcount.
