Born in the Chicago suburbs, Webb is a graduate of Indiana University. She originally attended the School of Music on a full-scholarship for clarinet performance. Music was an early and important part of her life: she attended piano and music theory lessons starting at age four and continued to study other instruments until dropping out of the music program after one year of study. She stayed at the University and graduated with a degree in political science and concentration in economics. She later attended and graduated from the Columbia University Graduate School of Journalism.

After college, Webb moved to Iwate Prefecture in northern Japan. There, she freelanced for several publications, covering technology and pop culture. Additionally, she was one of the founding anchors of "Furai Iwate," which was a weekly show on IBC Television that discussed local government and the economy. Webb continued to work throughout Asia for Newsweek, The Wall Street Journal and other publications until she returned to the United States in 2004.

In 2005, Webb had been working on numerous initiatives to aid in the digital transformation of journalism. To show that people could survive without print or broadcast media, Webb undertook a 30-day experiment. Calling it a "digital diet," Webb chronicled her month without newspapers, magazines, television, radio - even billboards and printed fliers. . Her results were shared throughout college journalism classrooms and on various shows about the media.

Webb later founded a digital media consulting firm, Webbmedia Group, to help media and other organizations adapt technology for journalism.