About Avenues


Todd Shy
Todd Shy
Head of Upper Division

Todd Shy joined Avenues in 2012 as a humanities instructor for the middle grades and as a middle school administrative team member. He went on to become the director of the mastery program and the program director of High Intensity Practice in writing. As a founding member of Avenues New York, Todd has a unique, overarching perspective of the dynamic culture and curriculum of the middle and upper grades.

Looking to expand his experiences in school leadership, during the 2017–18 school year, Todd moved on to pursue a position as an upper school head for grades 5 through 8 at Town School for Boys in San Francisco, California, where he oversaw the academic program, supervised faculty members and spearheaded an 8th grade capstone experience. While his time at Town School was a formative and valuable experience, there was always a desire to return to Avenues, where he had cemented much of the middle and upper grades programming we now know. Quite fortuitously, a leadership position had soon after become available and we had the pleasure of welcoming Todd back to our community in the fall of 2018 to assume the role of head of Upper Division.

Prior to Avenues, Todd served as a middle school social studies department chair at Cary Academy in Cary, North Carolina, as well as a philosophy instructor at North Carolina Governor’s School in Raleigh, and a history teacher for middle and upper grades at Rocky Mount Academy in Rocky Mount, NC. He is also an experienced book critic for national publications, such as The San Francisco Chronicle, The Southern Review and others.

Todd received a B.A. from the University of Virginia, completed graduate coursework at King’s College of London and obtained a master of divinity from Princeton Theological Seminary.

When not in school, Todd enjoys reading, taking long city walks, and idling by the ocean whenever possible.

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