Web Administrator 101

I am our wards Website Administrator. I've looked for a core beginner's How To document and have not found it. Suggestions?
At the moment I am not able to figure out how to assign two different images to a single Ward leader holding two different positions.
In fact, I can't figure out where the assignment of any image to a position is. Can someone point the way? Thank you.

Images are not put in by position, but rather in the directory under either the individual's personal record or household record. When you upload their picture, it will auto populate to the leadership record.