Robert Scoble joined Microsoft in May 2003. Scoble was part of the Channel9 MSDN Video team, where he produced videos that showcased Microsoft employees and products.

Although Scoble often promoted Microsoft products like Tablet PCs and Windows Vista, he also frequently criticized his own employer and praised its competitors (such as Apple Computer and Google). He was unusual in the level of access he offered to his users, which included publishing his cell phone number on his blog and urging people to contact him directly with issues, as well as accepting comments on his blog.

The Economist described Robert Scoble's influence in its February 15 2005 edition•:


On June 10 2006 Scoble announced• he was leaving Microsoft to join Podtech.net as vice president of media development with salary raise from less than $100,000 (in Microsoft) to over $100,000 and accompanied by "a quite aggressive stock option" offer that could make him wealthy if his new company succeeds.••• According to Alexa Internet this day has the biggest traffic to his blog and PodTech over their lifetime.• June 28 2006 was his last day at Microsoft.