Born in Caibarién, Villa Clara Province,[2] she took part in track and field as a teenager and at the age of eighteen she cleared fifty metres in the javelin for the first time, setting a personal best mark of 52.10 m,[3] and became the Cuban junior champion.

[3][6] Caballero came third at both the Barrientos Memorial and Olimpiada del Deporte Cubano in Havana in 2010 (improving her best mark to 59.30 then 59.92 m).

[7] Havana was again the venue for her first throw over sixty metres in 2011, as she had a mark of 60.50 m then won the Barrientos meet a week later with a best of 62.94 m.[8] This earned her a spot at the 2011 World Championships in Athletics and she reached the final round, finishing ninth with a mark of 60.73 m.[3] She had much success regionally that year, winning the gold medal at the 2011 Central American and Caribbean Championships in Athletics,[9] as well as a bronze medal at the 2011 Pan American Games (an event won by fellow Cuban Yarelys Barrios).

[10][11] A throw of 65.60 m in March 2012 lifted her to fourth in the world rankings and she was later chosen to perform in the discus alongside Barrios in 2012 Cuban Olympic squad.

[14] In 2015, as well as setting a new personal best, she won the Pan American Games, and produced a shock upset, beating pre-competition favourite Sandra Perkovic to win the World Championship.