Dain had been the head coach at Olathe Northwest since 2003, when the school first opened.
In the fall of 2003 the program's highest level of football competition was JV, which Dain coached. Since 2004, Olathe Northwest has had a varsity team under Dain.
During his nine seasons as the varsity head coach Dain compiled a 27-57 record. Despite an overall winning percentage of just .321, the Ravens qualified for the playoffs in 2006, 2009 and 2011.
Dain's best squad, on paper, came in 2011 when his Ravens went 5-5 and made a Regional appearance in the state playoffs. The star player on that year's team was their 6-foot-10 wide receiver Willie Cauley-Stein, who's now noted for his success on the basketball court at the University of Kentucky.
Prior to his arrival at Olathe Northwest, Dain was the head coach at SM East from 2000 to 2002. During his time with the Lancers he compiled a 13-18 record. Included in those 13 wins was a Sub-State berth in 2001 and a Sectional appearance in 2002.
Prior to his first head coaching gig at SM East, Dain served as an assistant coach at SM West.