The 2022-23 saw Conwright push the Crimson women to a sweep of the Ivy League Heptagonal Championships. At the 2023 Ivy League Heptagonal Championships, Crimson student-athletes won Ivy League titles in the women's 200m, women's 400m and the women's 4x400m relay. Conwright coached the Crimson to even more success at the 2023 Ivy League Heptagonal Outdoor Championships, as seven Crimson earned All-Ivy League honors.

Conwright's first season with the Harvard coaching staff during the 2021-22 season saw student-athletes excel throughout the season. The Crimson women won the 2022 Ivy League Heptagonal Indoor Championship, as Tina Martin won Ivy League titles in the 60m and the 200m. 

As a sprinter at Cal Poly San Luis Obispo, Conwright was a 3 time all-American in the 100m from 1998-2000 where he finished 5th, 7th, and 3rd respectively.He was a 2 time all-American in the 200m placing 5th in 1998 and 7th in 1999. In the Big West Conference, he was a 4-time champion in the 100m from the years of 1996-2000 where he still holds the conference record at 10.12. He later went on to run a 10.10 at the national championships that same year at Duke University. He was also a 2-time Big West Conference champion in the 200m. 

In 1999, he ran first leg on the gold medal winning 4 × 100 m relay at the World University Games in Palma De Mallorca, Spain. He was also a finalist in the 200m in the same championships. In 2001, he made his second national team where he ran first leg on the silver medal winning 4 × 100 m relay at the World University Games in Beijing, China.

At the 2002 IAAF World Cup, he was called to replace an injuried Tim Montgomery on the 4 x 100 relay. Together  with Jon Drummond, Jason Smoots and Coby Miller, he ran third leg setting a World cup Record of 37.92. At the 2006 IAAF World Cup he lead off  the 4 x 100 metres relay again, this time with Wallace Spearmon, Tyson Gay and Jason Smoots, breaking the previous championship record by setting a new record of 37.59 seconds.

In his professional career, Kaaron competed trained with HSI under the tutelage of John Smith from 2002 to 2007. Kaaron was able to compete in two Olympic Trials Championships. 2000 and 2004. He also competed in every US National Championships from 2000-2007, making the finals in both 2003 and 2006. 

His personal best time over 100 metres is 10.05 seconds, achieved in July 2000 in Flagstaff. Although his best performance cane in the 2003 National Championships at Stanford University running a 10.16 into a -1.6 headwind. Unfortunately, while leading his semi-final heat, he pulled up 20 meters from the finish line. Although he still managed to make the finals running 10.24, he was unable to run due to injury. His personal best time over 60 metres is 6.61 seconds, achieved in March 2003 in Boston. In the 200 metres, he has 20.59 seconds, achieved in July 2002 in Rome

Kaaron served as Head sprint coach for the National Korean Federation for one year, 2007 through 2008, before returning home and taking an assistant coaching position with John Smith from 2009-2021. During this period, Kaaron was able to coach athletes such as Carmelita Jeter, Jason Richardson, Tyson Gay, Gil Roberts, Ryan Bailey and Michael Cherry.