Following college, Rosensweig's first job was at Dictaphone, then an independent subsidiary of Pitney Bowes, selling word processors door-to-door in Manhattan.

[2] In 1996, Rosensweig led the Ziff Davis launch of a series of Internet print magazines, including, by license, the acclaimed Yahoo!

[4] During his tenure at CNET, Rosensweig served as a key participant in company-wide efforts to develop and introduce innovative new Internet advertising formats, such as interactive messaging.

In 2007, Rosensweig became a partner of private investment firm Quadrangle Group, founded by Steven Rattner, opening an office in Silicon Valley.

[8] In February 2010, Rosensweig joined Chegg as president and CEO,[9] where he has overseen expansion and multiple acquisitions, and heads operations and executive management.