Mr. Churchill has been at the forefront of the e-business since its inception in 1994. After founding his 2nd company at the age of twenty-five, called Alternative Edge, Mr. Churchill was successful in integrating three sales channels: brick and mortar, mail order, and website. The Alternative Edge grew to a staff of 30 people and was the recipient of two awards in 1995; "Retailer of the Year" and "Small Business of the Year". The company was eventually sold to a large sporting goods company and the Alternative Edge still lives on today.

Mr. Churchill then founded the online media division of USWeb in Sausalito California and pioneered rich media placement online. Between 1997 and 2000, Mr. Churchill played a pivotal role at Left Field and McCann-Erickson where he developed campaigns for large blue chip corporations such as REI.com, Macy.com, Sun Microsystems, Amazon.com, Sprint IPT and Microsoft. In 2000 he moved to Ask Jeeves where he was responsible for the management of a $40 million advertising budget before growing two Syndication Departments (San Francisco and New York) to a network of over 50 Internet sites, including Overture, MSN, Lycos, AT&T, and About.com. The Syndication Department eventually rose to contribute over one third of Ask Jeeves total advertising revenues.

During his tenure at Ask Jeeves, Mr. Churchill was the visionary responsible for reducing the number of ad units per page view and introducing Ask Jeeves to "paid listings". Now considered the company's main revenue driver and most successful product to date, "paid listings" are responsible for Ask Jeeve's recent declaration of profitability.