Does the managerial title of a LoR writter matter? In the past I have seen students eager to get a recommendation from a proffesor from the upper management like the dean of the faculty. Especially for academic endevours such as grad. school applications. Or similarly a letter from the superindendant of the highschool for undergraduate applications. Would it be relevant that the LoR writer is in the upper management of the university or would the writer be recognized by their academic standing and nothing else. Please note that I am asking this question for student level research oriented applications.
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.