[13] He later held management and leadership positions at Bay Networks, Quantum Corporation, and Thomas-Conrad Corporation and was Senior Vice President and Chief Information Officer at Gateway, Inc. From 1999 to 2006, Webb held various titles at eBay, including President of Technology and Chief Operating Officer.

[12] Webb's second book, Dear Founder: Letters of Advice for Anyone Who Leads, Manages, or Wants to Start a Business,[17] with a Foreword by Howard Schultz, former executive chairman and CEO of Starbucks, was published by St. Martin's Press on September 11, 2018.

[5] Startups that WIN funds have access to a network of 89 industry experts from companies such as Google, PayPal, Oracle, and Hewlett-Packard.

[5] WIN is considered to be part of a trend of smaller, early-stage funds that are indirectly challenging the traditional venture capital model.

[5] Webb and his wife Irene founded the Webb Family Foundation in 2004,[13] an organization dedicated to “promoting meritocracy through helping underdogs in society meet their full potential.”[19] Through grants, the foundation has supported disaster relief, youth mentoring, cancer research, education, and other organizations.