Meanwhile, Microsoft has seen several CEOs since it was launched by Bill Gates in 1975, and has evolved under different leaders, most recently, CEO Satya Nadella. As a result, it emphasizes "good communication and (staff) don't have to touch on all areas of the business," said Medina.
So, which of the two would he recommend?
Well, neither, actually. After eight years working his pick of "juicy, sexy jobs" at Amazon and Microsoft, in 2011 Medina decided to jump ship and launch his own start-up – something, in hindsight, he said he wishes he'd done sooner.
"My life is not a very good example of a good life lived," he said. "If I were to do it again today, I would work at a start-up straightaway."
"The amount of experience you get at a start-up is far greater and the basket of problems you can work on on any given day is so large and so insightful it can satisfy any curiosity."
However, his experience learning from two of the best has certainly come in handy. After his first business failed, Medina and his three fellow co-founders created Outreach, a communications platform for salespeople, which is today valued at $500 million.
Medina said he runs it like a hybrid of the two tech behemoths.
"Economically we look like a Microsoft," said Medina, referring to company's high-margin, service-based business model.
"But we also take learnings from Amazon," he continued, noting that, despite its huge growth, Amazon has maintained a "Day one" mentality, which provides a good model for start-ups.
"Even though it feels like we're winning, we're growing, you can't take your eye off the ball: The market is very vast," said Medina.
"So as CEO I try to understand the minute detail. I use Amazon tactics to drive Microsoft growth."
CNBC Make It reached out to Amazon and Microsoft for comment, but they were not available to respond at the time of publishing.
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