There’s only one first for everything, and when it comes to Microsoft personnel, this honor befell Marc McDonald. Bill Gates and Paul Allen may have founded the company, but McDonald was Microsoft’s very first hire. In fact, the software developer’s fate was so intertwined with the company that he ended up working for it not once, but twice.
Like some other people on this list, however, McDonald had some issues with the company’s rapid growth, and decided to leave the nascent supercorporation in 1984 for smaller pastures — namely, Allen’s new company Asymetrix, where he also managed to be the first hired employee. However, Microsoft came knocking again in 2000. At the time, McDonald was with Design Intelligence … which Microsoft bought, so he found himself working for the company once more.
This time, McDonald stayed with Microsoft a while longer. In 2011, he left his principal development engineer gig for a job with MindMode, and in 2013, he started working at his most recent position as a software architect for the display ad company PaperG.