*note: this is an answer that assumes you're new, which you're not, but I figure new people might read it.
Call his coach once and make sure that he's dropped. If you get a message that says he might consider you if his top choices don't work out, then you're going to need to throw STs at him, and once the STs indicate that he's interested NOW, you can battle for him.
If he's never going to consider you, stop trying.
And if he's willing to talk to you right away, you're ready to fight right away.
But either way, once you're fighting vs. a sim, I'd use enough HVs/CVs/calls to get on his considering list, then send just one HV or a CV each cycle until you're in the lead. That way there's less chance that you overspend.