Rosenstein dropped out of a graduate program in computer science at Stanford in 2004 to join Google as a product manager. At Google, Rosenstein led projects in Google's communication and collaboration division. His projects initially included Google Page Creator, the precursor to Google Sites, and a project internally codenamed “Platypus,” which eventually became Google Drive. He also created and wrote the original prototype for Gmail Chat and many of the features in Google’s rich text editor.
In May 2007, Rosenstein left Google to become an engineering lead at Facebook, working closely with Mark Zuckerberg and Dustin Moskovitz. He was technical lead in charge of Facebook's Pages, the Facebook Like button, and Facebook Beacon.
In October 2008, Rosenstein left Facebook to co-found the collaborative software company Asana along with Moskovitz. On its website, Asana states its mission is to “help humanity thrive by enabling all teams to work together effortlessly.” He is a frequent speaker on issues of business and technology. He has published opinions on building effective collaborative software in Wired, leadership strategy and enterprise software design in Fast Company, and entrepreneurship in TechCrunch, and productivity in TIME.