Rabbi Stein grew up in Boston, MA, where he attended Maimonides School. Following high school, he studied for two years at Yeshivat Kerem B’Yavneh and then at Yeshiva University where he earned his BA in English Literature and his rabbinic ordination at the Rabbi Isaac Elchanan Theological Seminary. He has taught and worked as a school administrator at Ramaz, Salanter Akiba Riverdale Academy (SAR), and Ma’ayanot Yeshiva High School for Girls. From 2014 to 2021, he has served as the High School Principal at Farber Hebrew Day School.  At Farber, he worked closely with teachers, administrators, students and parents to create a warm, Torah-oriented environment with a rigorous and innovative academic program.