Jonathan Penn, the winningest volleyball coach in school history, joined Vassar in 1996 as head women's volleyball coach.
Penn coached the Brewers to the 2005 NCAA Division III Tournament, the fourth time in his career (2001, 2002, 2003). In 2001 and 2002, Vassar advanced to the regional semi-finals. Most impressively, Penn has led the Brewers to five straight Liberty League Championships in 2001, 2002, 2003, 2004 and 2005. The 2005 title was accomplished in near-perfect fashion, three straight sweeps of St. Lawrence, Union and Skidmore and a four-game win over Clarkson.
On September 18, 2004, Vassar defeated Brockport, 3-1, making Penn the winningest volleyball coach in Vassar history. He finished the 2007-08 seasons with a 221-135 record with the women's program and a 130-142 record with the men's team, a combined 351-277 mark.
In Penn's ten seasons at the helm, Vassar reached the post season five times, the 2005 team participating in the in the New York State and NCAA Division III Tournaments. In Penn's first season, Vassar finished fourth in the New York State Women's Collegiate Athletic Association Championship.
Active with the American Volleyball Coaches Association (AVCA) and NYWSCAA, Penn arrived at Vassar from Santa Monica (Calif.) College were he began coaching in 1989. At Santa Monica, he served two years as the women's assistant, three as the women's associate coach. In addition, he was the men's associate coach for three years and the head coach for three seasons.
While completing a bachelor's degree in English from UCLA in 1990 and a master's degree in Education at California State University at Hayward in 1993, Penn worked with various youth and adult programs in the greater Los Angeles area. He also served as a counselor at numerous volleyball camps.
As scholarship player at Penn State, Penn won championships on Junior Olympic squads and later competed in the Olympic Festival. In 2003, 2004, 2005, he has coached and played in New York's Empire State Games and earned a bronze medal playing in the Masters Division all three years.
Penn and his wife Patricia have a son and a daughter, and reside in the Town of Poughkeepsie.