Jeff Bezos’s League of Shadows

By Brad Stone

Amazon can be a uniquely challenging place to work, with its question-mark emergencies and the occasionally volcanic outburst from the visionary chief executive. It’s a place where promotions are hard-fought and sometimes painfully public. But there is also a job at Amazon (AMZN) that is highly coveted throughout the company and that nearly anyone in business would kill for.

The man holding this job—and they have all been men so far—has had direct, almost unlimited access to Jeff Bezos for as long as two years. He follows Bezos around, travels with him, sits in on his meetings, and confers with him at the end of many workdays.

The job title is unofficially the “shadow” to the CEO, or more formally, the technical assistant or technical adviser.

Amazon CEO Jeff Bezos has had shadows since the late 90s. For the first few years, the role was usually filled by an executive who had joined the company in an acquisition and was struggling to find his place at the rapidly growing online retailer. Stig Leschly was one of the first shadows. He was the CEO of an online shopping marketplace, Exchange.com, when Amazon bought his company in 1999. Leschly then ran a failing service within Amazon called ZShops and was preparing to leave in late 2000 when he had lunch with Bezos and told him of his plans. Instead, Bezos asked him to become his shadow.

Leschly spent three months shadowing Bezos, and today, as CEO of charter school company Match Education, he remembers it as among the most valuable experiences of his career. “He would walk around and go into meetings, and I would get to follow. I had nothing to do. I would just sit there and observe,” Leschly says. “But then he’d have an idea, and he would give it to me to figure out.” One of Bezos’s far-out propositions, Leschly recalls, was to build a distributed overnight delivery network that put Amazon inventory into the private homes of regular people, so it could be delivered to nearby customers overnight. (The idea was quickly proven wildly impractical.)

“I was a receptacle for him for any of the 19 ongoing activities in his brain that didn’t have a place in the normal organization,” says Leschly. “It was honest to god one of the most extraordinary things a young person can do.”

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