You'd be moving three people into new roles at the same time.
The people you are moving up might not have the required skill set for the new roles.
Considering how he continued to run the draft when he got his current role, I think Elias would have issues walking away from his current responsibilities and would attempt to do both jobs.
Makes much more sense to simply hire an experienced CEO to take on a role that isn't about baseball, it's about running a business.