In 2009, she took third place in individual pursuit and omnium at the USA Cycling Elite Track National Championships.

She graduated from college in 2006 with a degree in political science and East Asian studies and moved to Chiang Mai, Thailand, in 2007 to teach English at a private school.

In 2008, she obtained a position teaching 9th grade world history at the Harker School in San Jose, California.

[6] However, she became more involved in track cycling, where she would make the USA Olympic team and train with them in Los Angeles.

[8][9] Because of the difficulty getting sponsors in women's track cycling and the removal of individual pursuit from the Olympic program, Jackson made the complete transition over to the triathlon.

[15] However, she rebounded to win her first full iron distance race at Ironman Coeur d'Alene, overcoming an 8-minute deficit out of the swim to beat opponents Amanda Stevens and Kim Schwabenbauer.