[3][4] She moved up in age category at the 2004 South American Under-23 Championships in Athletics and took third over 1500 m and broke the Colombian national record in the steeplechase with a time of 10:24.09 minutes for second place.

[6] Caballero's first senior medal came at the 2005 South American Championships in Athletics held in Cali, where she was the bronze medallist in the steeplechase.

[9] As national champion, she represented Colombia over the long-distance track events at the 2010 Central American and Caribbean Games.

An appearance at the 2011 Pan American Games saw her increase her track medal haul, as she placed third in the 10,000 m and also managed sixth in the 5000 m. She ran at the 2012 New York Half Marathon, but finished 26th in a high calibre field.

Caballero began 2013 with a South American record run at the NYC Half Marathon, completing the distance in 1:10:30 hours to take seventh place.