Once described as the "adult supervision" of the company because of his former experience at eBay, Amazon, and Drugstore.com, Raman would make sense as a refreshing change of pace from Mason. He has climbed the chain at Groupon quickly, starting as a senior vice president back in April and getting promoted, twice, to his eventual spot as COO by November. His latest step up came around the same time that rumors surfaced about Mason's self-ousting last November. Lefkofsky had wanted Mason to be more "vocal" about the falling stock, sources told The Wall Street Journal. As COO, Raman should have some thoughts on the financial side of things.
Analysts expect the board to tap someone with a strong "operating background" and "steer it toward a more traditional business," which would make Raman a good fit. Even as COO he inherited some of Mason's CEO responsibilities. "Hopefully I will take lots of burden off Andrew’s shoulders," he told Businessweek back when he got the job. Plus, Raman's previous experience also meshes with the company's push away from daily deals and into e-commerce.
While Raman is a "strong internal candidate," as MacMillan and Levy put it, it's not clear just yet whether he's absolutely the guy for the job. Lefkofsky and Leonsis are looking outside the company, too. In the meantime, Leonsis, with his experience at AOL during its mega rise and subsequent crash, should provide some much needed crisis control at the stumbling site.