Orlondo attended Lynnwood High School where he lettered in football, basketball, and baseball. In football he was All-Wesco in 1990 and 1991. After graduating from Lynnwood High in 1991, he attended Western Washington University (WWU). There, he played football and was an outstanding cornerback and punt returner. He finished at WWU with 20 pass interceptions, 160 tackles, and 89 punt returns. During his final year at WWU in 1995, he was a consensus 1st team NAIA All-American and the Columbia Football Association Defensive Player of the Year. He led the U.S. in pass interceptions with 10 and ranked ninth nationally in punt return average. In 1999, he was named to WWU’s All-Century football team as first-team in cornerback and as the punt returner.
After WWU, he joined the Canadian Football League (CFL) and after being picked-up by the Hamilton Tiger-Cats during his second season in the league, he emerged as a defensive standout. He was with the Tiger-Cats during 1997-99 then the last eight years of his thirteen-year CFL career with the Toronto (2001-08). He was named a division All-Star six times and a CFL All-Star five times.
After retiring from his football playing days, he spent one year in 2009 as a sports broadcaster for Rogers Sportsnet TV and radio Fan 590 as a football analyst. But then, it was back to CFL football as Toronto’s defensive backs coach in 2010. In 2011 he became their defensive coordinator and defensive backs coach. In 2013 he was named defensive coordinator for the Hamilton Tiger-Cats where he stayed for four years before becoming Fresno State’s defensive coordinator during 2016. He then returned to the Hamilton Tiger-Cats as assistant head coach before being named the Tiger-Cats head coach in 2018.