In 1990, Kaiss was hired as the head coach of Southwestern High School in Baltimore.
There he led a previously winless team to two straight winning seasons before leaving in 1992.
He spent five seasons as offensive coordinator there, winning back-to-back black national championships.
There he was reunited with former head coach Reggie Barlow, who he worked with at Alabama State University.
[5] In his first season, the Defenders finished with a league-best 9–1 record and appeared in the 2023 XFL Championship Game, losing 35–26 to the Arlington Renegades.