6. Paul "Blitz" Maritz
Paul Maritz has hopped furiously around head-honcho gigs for the past decade, flitting from one C-level exec role to another. He has tech chops, which helped his rise at Microsoft to govern both its server and client platform development. He resigned in 2000 just in time to dodge the Windows ME bullet.
Since then, he co-founded Pi Corp. (which got munched up by EMC), jumped to CEO of rabidly anti-Microsoft VMware in 2008, then to a CEO position with startup Pivotal in early 2013. This kind of corporate ADHD would have made Maritz a perfect match for Microsoft's flailing product development initiatives.