From 1919 to 1938, Webb was a writer and director, first with the Famous Players Film Company, then with Whitman Bennett (a production company) and Associated First National Theatres, Inc. (Bennett's distributor), then Fox Film Corporation, then Whitman Bennett (production company) and United Artists (Bennett's distributor), then Burr & Company, then Pathe, then Lee de Forest, Inspiration Pictures [fr], Tiffany Pictures, and then FitzPatrick Pictures.

Since 1933, Webb was a radio writer and producer with Batten Barton Durstine & Osborn, Inc., and since 1953, was its Western editor.

As director Webb attended The Collegiate School on the Upper West Side of Manhattan.

[5] Kenneth Webb married, on September 20, 1920, silent film actress Lorraine Frost (maiden; 1897–1993) in Manhattan, New York.

[6] His brother, Roy Webb, also composer and film director,[7] was one of his chief collaborators.