Does the managerial title of a LoR writter matter?
I would rather get a letter from a professor, even a lowly assistant professor, who knows you well and can attest to your ability and potential, than I would from a higher level person who may have little experience in what your research area entails. The purpose of such letters is to give the reader an assessment of your likelihood of success. If it can't do that then it will be discounted, no matter the position of the writer. 

However, in case the letter is just a general statement of your character and (easily found) accomplishments, then the dean's or superintendent's letter might be useful.