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. She repeated that feat at the 2005 Bolivarian Games. She never participated in international competition from 2006 to 2009 and re-emerged in 2010, focusing on longer distance races. She won a 5000 m and 10,000 metres double at the Colombian Championships in 2010. She won the 5000 m bronze at the 2010 Ibero-American Championships in Athletics with a personal best run of 15:50.18 minutes. As national champion, she represented Colombia over the long-distance track events at the 2010 Central American and Caribbean Games. She became the CAC Games champion in the 10,000 m and was elevated to the silver medal in the 5000 m after the disqualification of Rachael Marchand. She began competing in road running events towards the end of the year, placing second at the Medellín half marathon with a run of 73:18 minutes (a Colombian record) and winning the Bogotá 12K.