Caicedo is from the town of Santa Martha de Cuba in Ecuador's Tulcán Canton, from which he gets his nickname, Cubanito ("Little Cuban").

[1] Whilst at school, Caicedo was a member of a cycling club founded by one of his teachers, former Olympic racing cyclist Juan Carlos Rosero.

The club has also produced a number of other professional riders, including Richard Carapaz and Jhonatan Narváez.

[5] Prior to joining EF for 2019, he rode for the Colombian teams Bicicletas Strongman and Medellín.

[1][6] Caicedo was again selected by EF for the 2020 Giro d'Italia, where he won the race's third stage, forming part of the day's early breakaway before dropping the remainder of the breakaway riders alongside Giovanni Visconti in the closing stages before dropping Visconti with an attack and reaching the summit finish on Mount Etna alone, additionally taking the lead in the mountains classification.