He was a member of the Metropolitan Opera Company between 1901 and 1920 and later appeared in many films. He appeared as himself in the 1928 romantic comedy film The Cardboard Lover.
Towards the end of his career at the Metropolitan Opera, De Segurola also became an impresario. In 1916, he presented a four-week opera season at the Grand National Theatre in Havana, where his company included Geraldine Farrar and Pasquale Amato.
After his retirement from the stage, he taught singing. Amongst his many pupils was Deanna Durbin.