Jay worked at Choate Rosemary Hall for twelve years as a teacher, coach, and the director of Community Service. In 1996, Jay and his wife Whiz left Choate to move to Southborough, Mass., for four years. During this time, Whiz worked as the Dean of Students at St. Mark's School while Jay answered the call to ordination in the Episcopal Church. Starting at Andover-Newton Theological School, Jay switched into the Master of Divinity program at Harvard in 1998. In 1998, the couple also became parents to Jack who is a third grader at St. Anne's Episcopal School.
Following his graduation in 2000, Jay was ordained into the transitional diaconate in 2002 and became a priest in June of 2003. Since earning his M.Div., Jay has been working as a chaplain, teacher, coach, and community service director at St. Andrew's School in Delaware. He is currently very interested in the connection between sports and spirituality and wrote his master's thesis on this subject.