Born on May 23, 1872, in Shelby, Cleveland County, North Carolina,[1] Webb attended the Shelby Military Institute and received an Artium Baccalaureus degree in 1893 from Wake Forest College, then attended the University of North Carolina School of Law in 1893 and 1894.[2] He was admitted to the bar and entered private practice in Shelby starting in 1894.[1] He attended the University of Virginia School of Law in 1896 and completed a postgraduate course.[2] He was a member of the North Carolina Senate in 1901.[1] Webb was appointed a trustee of Wake Forest College in 1898.[2] He was appointed trustee of the Agricultural and Mechanical College of Raleigh (now North Carolina State University) by the legislature in 1899 and served two years.[2] He was Chairman of the Democratic senatorial district in 1896.[2] He was Chairman of the Democratic county executive committee from 1898 to 1902.[2] He was temporary Chairman of the Democratic State convention in 1900.[2]