Olen was promoted to his current position of first assistant prior to the 2005-06 campaign after spending one season as the team's second assistant in 2004-05. He is actively involved with all aspects of the program, including travel, recruiting, scouting and game planning.

Alongside Carlson and former assistant coach Andy Aguinaldo, Olen helped lead the Tritons to an 18-12 overall record in 2007-08, which is the program's best mark in 10 seasons at the Division II level. UCSD rose to the occasion in the postseason, winning its first CCAA Tournament Championship to earn an automatic bid in the NCAA D-II West Regional for the first time in program history.

During his tenure at UCSD, Olen has helped guide the Tritons to some of the program's most successful campaigns. The Tritons recorded their first winning season at the D-II level in 2005-06, finishing the year with a 15-14 overall record. UCSD also finished fourth in the CCAA that season with a league tally of 12-8, marking the program's first winning record in conference play.

In 2008-09, the Tritons finished with an overall record of 17-11, recording back-to-back winning seasons for the first time at the Division II level.

Olen graduated from Spring Hill College in 2004 with a degree in Finance. He helped the Badgers to three straight appearances in the NAIA National Tournament, including trips to the NAIA Elite Eight in 2000 and 2001.