Cherlow's rabbinic career began in Kibbutz Tirat Zvi, where he served as a rabbi and teacher.

After the Rabin assassination, he helped found Tzohar, whose aim was to lessen the tensions between religious and non-religious communities.

He has also published books that deal with Bible commentary as well as the writings of Rabbi Avraham Yitzhak Kook.

[4] Cherlow has voiced empathy for the difficulties faced by religious homosexual people, and has called for the Orthodox community to treat them with compassion.

Cherlow has voiced liberal positions on some issues, such as allowing the use of artificial insemination by unmarried women in certain circumstances and supporting coed activities in Bnei Akiva.

[5] He is opposed to civil disobedience, an issue that rose to the fore during Israel's unilateral disengagement from Gaza and evacuation of Israeli settlements in the region.

In 2012, Cherlow called on the State of Israel to recognise non-Orthodox streams of Judaism and Reform conversions.