Cherlow's rabbinic career began in Kibbutz Tirat Tzvi, where he served as a rabbi and teacher. Later he served as a rabbi in Yeshivat HaGolan in Hispin, in the southern Golan Heights. After the Rabin assassination, he helped found Tzohar, whose aim was to lessen the tensions between religious and non-religious communities. In 1998 he founded a Yeshivat Hesder in Petach Tikva, later to become Yeshivat Hesder Amit Orot Shaul in Kfar Batya, Raanana. He justified his decision to start a new yeshiva in the central area of Israel by saying that it is the place where the most important debates about the identity of the country take place.