Born in Baeza,[1] Olid grew up in the household of the governor of Cuba, Diego Velázquez de Cuéllar.
On January 10, 1519, Olid sailed with Hernán Cortés's fleet, as his quartermaster, and took an active part in the conquest of the Aztec Empire.
During the Siege of Tenochtitlan, Cristóbal was one of Cortés' key captains, playing a critical role in the capture of Xochimilco.
[2]: 315, 317, 319, 333, 339, 340–343 Cristobal was the Texcoco camp commander during the trial of Antonio de Villafana, for his plot to assassinate Cortés.
[2]: 413 In 1522, Olid led Spanish soldiers with Tlaxcalan allies in the conquests of Jalisco and Colima in West Mexico .