After college he was working for Fawcette Technical Publications (as anything man - design, editing, helping plan the conferences like VBITS and VSLive!). His current wife Maryam was also working for Fawcette.

During the mid-90's Robert helped co-chair the Visual Basic SIG for SDForum, and was a frequent attendee and organizer for numerous local tech user groups.

In the late 90's Robert worked for Winnov (manufacturer of webcams) supporting webcam users and was very active in Microsoft's NetMeeting support newsgroups. He was named a Microsoft MVP for this activity and maintaining a busy NetMeeting information website. He retained his MVP status up to the time he became a Microsoft employee.

Dave Winer had told him "that blogging was hot," so he left Fawcette and joined Winer's UserLand Software, which was a content management and blogging software startup. He worked for John Robb as Director of Marketing. After the startup ran out of money and was unable to pay his salary, Robert worked for free for a month and eventually had to switch jobs.

He found a job at NEC Mobile Solutions from a Craigslist posting as Sales Support Manager for TabletPC. His job responsibility was to answer all the phones and all the emails with support/sales requests. He had started using blogs (a skill learned in UserLand) to provide tech support and listen to feedback from NEC customers.

His blog was noticed by Vic Gundotra (then General Manager of Platform Evangelism at Microsoft), and Robert accepted his offer to work at Microsoft. Scoble has long been a prominent advocate of both RSS technology and the Tablet PC.[9][6]