Mr. 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, Mr. Pickard was transferred to the Washington, D.C., field office, where he worked in an undercover capacity on the case code-named "ABSCAM." In July 1980, Mr. Pickard was promoted to FBI Headquarters, serving in the Inspection and Criminal Investigative Divisions. In October 1984, Mr. Pickard reported to the New York City field office as a supervisor in the White-Collar Crime Section and later was appointed to be the Assistant Special Agent in Charge for all White-Collar Crime investigations and violent crime matters in New York.

In 1989, Mr. Pickard was selected for the FBI's Senior Executive Service and was transferred to FBI Headquarters, where he oversaw the FBI's finance operations and subsequently its personnel operations. In 1993, Mr. 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 World Trade Center defendants, the trail of the Blind Sheik and his co-conspirators, the Manila Air conviction of Ramzi Youssef and his associates, and the July 1996, TWA Flight 800 explosion.

On September 10, 1996, FBI Director Louis Freeh named Mr. Pickard to the position of Assistant Director in Charge of the Washington field office (WFO). During his tenure at WFO, Mr. 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 Aimal Kasi.

On February 2, 1998, Mr. Pickard assumed the position of Assistant Director of the FBI's Criminal Investigative Division at FBI Headquarters. On November 1, 1999, Mr. Pickard was appointed Deputy Director, the number two position at the FBI. On June 25, 2001, Mr Pickard was appointed Acting Director of the FBI by Attorney General John Ashcroft.