Figueroa played college baseball at the University of Florida while majoring in Sports Management.

Figueroa split the 2009 campaign between the Single-A Fort Wayne TinCaps and High-A Lake Elsinore Storm.

[6] Figueroa spent the 2010 season back with Lake Elsinore, playing in 124 games and hitting .303/.408/.392 with four home runs, 66 RBI, and 26 stolen bases.

[7] The Padres traded Figueroa to the Tampa Bay Rays along with Brandon Gomes, Cesar Ramos, and Adam Russell in exchange for Jason Bartlett on December 17, 2010.

On December 12, 2014, Figueroa signed a minor league contract with the New York Yankees organization.

[16] On April 2, 2016, it was announced that Figueroa would make the Pirates' Opening Day roster as a reserve infielder, beating out offseason acquisition Jason Rogers and incumbent Pedro Florimón for the job.

Figueroa made his Pirates debut on April 8, 2016, fouling out to third base in a pinch hit appearance.

[20][21] On December 16, 2021, the Tampa Bay Rays announced that Figueroa had been promoted to serve as the team's director of baseball operations.