Greenhills Hires Sylvester Cutler as Director of Admission

Greenhills School has appointed Sylvester Cutler to be its new director of admission and financial aid, effective July 1, 2021. Cutler will serve on the school’s senior leadership team and oversee student recruitment, community outreach, and manage the more than $1.6 million of financial aid Greenhills distributes each year.

“Sylvester understands and appreciates our enrollment management landscape here in the Ann Arbor area because it’s not dissimilar to what he’s experienced in the Milwaukee area,” said Greenhills Head of School Peter Fayroian. “He brings incredible experience and tremendous vision to the job, and most importantly, he brings a passion for young people demonstrated at the school leadership level, and as a teacher and coach. We are very much looking forward to Sylvester and his family joining us at Greenhills and in Ann Arbor.”

Cutler comes to Greenhills from the University School of Milwaukee, where he has worked since 2011, including more than six years as associate director of enrollment management and director of financial aid. He has taught and served in numerous leadership roles, including assistant dean of students and head coach of its varsity boys basketball program.

“I’m passionate about admission work because I know schools like Greenhills can be transformative for students,” said Cutler. “Greenhills is well known for helping students learn what they’re capable of, then helping them get there, and I’m excited to connect prospective families with that experience.”

After earning his bachelor’s degree from Marquette University, Cutler went on to earn a master’s degree in administrative leadership, with specialization in higher education, from the University of Wisconsin-Milwaukee. There he earned his certificate of nonprofit management. Other credentials include certification as an international advancement professional at senior level from Independent School Management, and a mini-MBA certificate program from Loyola University-Chicago.

Cutler will be joined by his wife, Laura, and two children, Dalton (2) and Ada (11 months).