From 1979 to 1998, Osborne was assistant athletic director at Nebraska, first under Bob Devaney then under Bill Byrne.

On October 16, 2007, Osborne was announced as the interim athletic director. In 2010, Osborne ended Nebraska’s long-standing relationship with the Big 12 Conference and accepted an invitation for Nebraska to become the twelfth member of the Big Ten Conference. On December 19, 2010 Nebraska removed the interim tag from Osborne’s title and announced he would remain as athletic director through June 30, 2010. Osborne later agreed to continue as athletic director after 2010, with his position to be reviewed annually. On September 26, 2012, Osborne announced his retirement as athletic director, effective January 1, 2013. Osborne officially resigned on January 2, 2013, after returning to Lincoln with the Huskers football team following their participation in the Capital One Bowl.

Today, he is very involved his TeamMates Mentoring Program founded in 1991 with his wife. TeamMates provides support and encouragement to school aged youth. The goal of the program is to see youth graduate from high school and pursue post-secondary education. To reach this goal, youth meet one hour per week with a caring adult who serves as a mentor. Mentors are volunteers from the community who have dedicated themselves to making a difference in the life of a young person. Mentors give youth a sense of hope, purpose and vision. The TeamMates Mentoring Program currently provides a mentor for over 7,000 youth across Nebraska and Iowa, as well as in San Diego, California.