Shearer began his career at Transylvania as vice president for finance in 1979 and in 1981 took on the additional responsibilities of chief development officer.
In the spring of 1999, Shearer was inducted into the University of Kentucky's Gatton College of Business and Economics Alumni Hall of Fame in recognition of his success and achievements.
At the October 24, 2009, Board of Trustees meeting Shearer made the surprise announcement that he would retire as president effective June 30, 2010.
Shearer plans on remaining at Transylvania as a part-time professor in microeconomics in the initial phase of his retirement.
On April 14, 2010, the Board of Trustees named historian and former businessman R. Owen Williams as Shearer's successor.