Leonard Lai left his career as an engineer and delved into the film industry. He started out as the Script and Continuity Supervisor on the feature film Perth directed by Djinn Ong and then the Hong Kong-Singapore Production Hainan Chicken Rice directed by Kenneth Bi. He also worked in the same position for Jack Neo's Best Bet and MTV's drama Rogue. He was also the 1st Assistant Director for Jack Neo’s We Not Naughty.
Leonard Lai's directorial work includes short documentary A Family Reunion and short film Mr Charles de Gualle. His debut feature film, The High Cost of Living won the award of Best Feature Film at the 9th International. Panorama of Independent Film makers 2007 in Greece.
In recent years, he has produced 12 feature films including the All-Time Highest Box-Office Singapore Film Ah Boys to Men 2.
He is currently the Business Development Manager and Producer of J Team Productions.