In 1993, Gragg was hired as an academic counselor at Vanderbilt University. Soon after he was promoted to director of student life in the athletics department. From 1995 to 1997, he was director of compliance at the University of Missouri. He went on to the University of Michigan, where he was an assistant athletic director from 1997 to 2000. Gragg joined the University of Arkansas athletic department in 2000 as an associate athletic director. In 2003, he was promoted to senior associate athletic director and then deputy director.
Eastern Michigan (2006–13)
On February 21, 2006, Gragg was named the new director of athletics at Eastern Michigan University in Ypsilanti, Michigan. At EMU, Gragg was responsible for an intercollegiate athletic program with 21 teams, 550 student-athletes and 80 staff members. Under his leadership, the Eastern Michigan Eagles totaled 24 Mid-American Conference team championships, 32 MAC Coach of the Year awards, 38 MAC Player of the Year honors and 164 individual MAC champions. Gragg also spearheaded construction of EMU's $3.9 million multipurpose indoor athletic practice facility. In March 2013, it was announced that Gragg would leave Eastern Michigan University for Tulsa University. His seven years as EMU athletic director was the longest tenure since Gene Smith oversaw the department from 1986 to 1993.
Tulsa (2013–present)
On March 22, 2013, Gragg was officially introduced as the new vice president and athletic director at the University of Tulsa in Tulsa, Oklahoma. He was the first Vanderbilt Commodore football alumnus to become athletic director of a major NCAA Division I university. Following a 10-year tenure in C-USA, the Golden Hurricane were upgraded to the American Athletic Conference in 2014, shortly after Gragg's arrival. They won four AAC championships in the 2014 season, including conference titles in men's and women's cross country and men's soccer. In the 2013–14 season, the Tulsa basketball team won 11 games in a row and earned its first NCAA Tournament bid since 2003. They made the tournament again in 2016, losing in the first round both times. Over the course of his career, Gragg has been a presenter and panelist at events including the NCAA Presidential Summit, Future Coaches Academy, Champions for Athletic Director and Football Coaches, and the NCAA Annual Convention. He is a member of the National Association of Collegiate Directors of Athletics and the Black Coaches & Administrators.
Book
In October 2015, Gragg's book 40 Days of Direction: Life Lessons From the Talented Ten was published. It relates the personal experiences of Gragg and 10 of his Commodore football teammates as African American student-athletes on the predominantly white campus of Vanderbilt University, and demonstrates how those experiences would shape their personal and professional lives, offering a blueprint for success.
Honors and awards
Black Coaches & Administrators Administrator of the Year, 2008–09
Huntsville-Madison County Athletic Hall of Fame, 2010