I’ve been at Microsoft a long time, and worked in a variety of businesses from Windows to Online and everything in between. I know what it’s like to pitch the winning story vs the underdog story. And whether you are on top with market share (Windows) or fighting your way towards to middle (Bing), the sweet spot is all a matter of perspective.
This came to light for me again this week, while working on some of the details on the Yahoo-Bing deal and talking about the importance of customer choice, a varied marketplace, and the dangers of a monopoly when one company dominates (aka: Google). But wait, is this Microsoft talking? Or the old days of Linux? Or Netscape?
I have been on both sides of the game, and I talk to people all day who are also trying to choose their next career step: a risky Search start-up? Google? Bing? Stock price, salary, culture and benefits aside, I say to look at how you like to play the game. Do you like the thrill of already winning, or the climb to get there?