He graduated from Saint Francis College in Brooklyn with a BBA in accounting, and subsequently received his MBA in taxation from St. John's University in Jamaica, Queens.

Pickard began his career as a Special Agent of the FBI on January 13, 1975, and after a period of training, he was initially assigned to the New York City field office.

In April 1979, Pickard was transferred to the Washington, D.C., field office, where he worked in an undercover capacity on the case code-named "ABSCAM."

In 1993, Pickard was transferred to the New York City Office once again, to serve as the Special Agent in Charge of the National Security Division, supervising such matters as the trials of the 1993 World Trade Center bombing defendants, the trial of Omar Abdel-Rahman and his co-conspirators, the Manila Air conviction of Ramzi Yousef and his associates, and the July 1996, TWA Flight 800 explosion.

During his tenure there, Pickard supervised such matters as the investigation and arrest of FBI Special Agent Earl Pitts for espionage and the capture of convicted CIA killer Mir Amir Kansi.