What I did, and I think Cat said it was a decent strategy, was to list them as the non-leadership category, but make my leadership role apparent from the title.
So for mine, I have entries under both 'Paid Employment, Non-medical' and 'Intercollegiate Athletics' which are titled "Head of Xyz". The 'Head of' is the tip-off that it is leadership.
The categories aren't everything, and you don't need to hit a quota for each one or anything...they're a quick-glance guide for the adcoms. But remember, adcoms aren't dumb, and they can read. If you put information in the title, it's still right there for them!