Clicking in this box will show you programs related to your search from schools that compensate us. Bigger cities tend to have higher entry-level teacher pay than small towns. Teachers teach for the love of the occupation, not for the money. From there, you may advance to serving as the head of your department, and from there, enter administrative positions like assistant principal, principal, and — maybe, eventually —— superintendent. Some teachers eventually crack under financial pressure and leave the profession for work in other industries that offer better salaries. Positions, like leading a club, leading after-school tutoring, and serving as a chaperone for dances or other school events, can be similarly lucrative. Comp Best Practices.