In 1871 Tilton, given his experience in teaching, received an eager offer from the Trustees of Phillips Academy for Principalship. He initially refused but eventually came to an agreement: $2,500 salary, an apartment in Double Brick House for him and his family, and the "approval of his views in regard to the administration of the Academy". He was in a lot of ways different from his predecessor Samuel Harvey Taylor. Tilton believed that students ought to choose where they want to continue their studies. Historically, most graduates attended Yale College, and could do so simply with a letter of recommendation from Taylor. Students who wanted to attend Harvard were unprepared and needed outside tutoring. He changed the school's curriculum so that it met the requirements of any college, including Harvard. He revamped subjects such as mathematics, classics, and modern language. At an extra cost, students could take courses in languages such as German and French with Professor Oscar Faulhaber. On Sundays, students were required to attend two church services held by the Andover Theological Seminary. Intended for older students of the seminary, Tilton's pupils found them uninteresting and difficult to understand. He adjusted the Sunday schedule so Phillips Academy students no longer had to attend a second church service. Instead, they had a vesper service where notable figures would give short speeches. They were not necessarily religious and proved to be popular among all. At the end of Tilton's first year, seventeen students matriculated at Harvard, and everyone else to "the college of their choice".
