Kaleo then transferred to the University of Maryland for his final two seasons. As a senior, he set single-season school records in passing yards (3,392), completions (286), attempts (482), total yards (3,472) as well as single-game touchdown passes with five. After his senior year, he participated in the Blue-Gray Football Classic.
He served two seasons, 2007 and 2008, as the offensive coordinator and quarterbacks coach for the Iona CollegeGaels. Newly hired Towson head coach Rob Ambrose selected Kaleo as his quarterbacks coach. He currently has two sons by the names of Parker and Carson.