Kaiss began coaching at Brooklyn High School and Andover High School, both in Maryland. 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.
In 1992, he was hired as the offensive coordinator, quarterback coach, and receivers coach at Morgan State University. In 1993, Keiss moved on to Southern University, where he served as running backs coach, recruiting coordinator, and special teams coordinator. There he won the Black College National Championship and SWAC Championship in 1993 and 1995. From 1997 to 1999, he served as special teams coordinator/wide receivers coach at Tennessee State University. In 2000, he became the offensive coordinator/receivers coach at Alabama A&M University.[2]
In 2001, he became the offensive coordinator and quarterbacks coach at Hampton University. He spent five seasons as offensive coordinator there, winning back-to-back black national championships.[3]
In 2006, he returned to Tennessee, where he served as offensive coordinator. He also served as a regional recruiting coordinator.
In 2011, he was hired to be the offensive coordinator at Alabama State University. There he served under head coach Reggie Barlow. In 2015, the Hornets moved on from both Barlow and Kaiss.
From 2015 to 2017, he served as the offensive coordinator at Alcorn State University.[4]
In 2022, Kaiss was announced as the offensive coordinator of the DC Defenders of the XFL. 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.
In 2025, Kaiss was named the UFL's Assistant Coach of the Year.[6]