Representing Madison High, he won two consecutive Eastern Regional titles in the one-meter event, and was named All-State in both his Junior and Senior years.

To remain competitive, he completed two-hour practices four days a week with New York's Morningside Diving Association coached by Jim Stillson, though it required a one hour commute each way.

[3][4][2][5] As a college athlete on the Ohio State University swimming & diving team under Head Coach Vince Panzano, where he was a 1988 graduate, he swept the three diving events (one-meter, three-meter and platform) at the Big Ten championship his senior year and was named conference Diver of the Year.

[7] Jeffrey twice won a bronze medal in 10-meter platform diving at the Pan American Games, both in 1991 at La Habana Province, Cuba and in 1995 at Mar del Plata, Argentina.

[8] In August 2014, he moved to Stanford University, where he is Head Diving Coach of the men's and women's collegiate teams.

[8] He also owns the Stanford Diving Club, which consists of teams of junior, senior, and masters divers who compete at the national and international level.