Gertrude Vanderbilt is one of very few women to have raced aboard an America's Cup yacht during an actual defense. She took an active role in the afterguard alongside her husband, Harold S. Vanderbilt, when he skippered ENTERPRISE, RAINBOW, and RANGER in successful Cup defenses. Harold Vanderbilt was the first to develop the timed start, forever known as the Vanderbilt start. It was Gertrude Vanderbilt who kept time for those starts, using analytical techniques developed by her husband. She was also a trusted observer and advisor concerning the conduct of the races.
Along with Olin and Rod Stephens, Sherman Hoyt and Arthur Knapp, Gertrude Vanderbilt was a full-fledged member of Mike Vanderbilt's champion afterguard through the 1930s.