Jeff Bezos’s League of Shadows

Photograph by Jin Lee/Bloomberg News

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 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,, 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.”

Amazon wasn’t the first technology company to employ shadows to the CEO. Intel has utilized the position for years. Former Chief Executive Paul Otellini, for example, was the technical assistant to one of his predecessors, famed Intel boss Andy Grove. At Intel and later at Amazon, the shadow served as a way to give rising execs additional exposure to the boss while giving the boss a way to mentor a subordinate and hear another opinion on critical matters. As a rising Intel executive in the 1970s, venture capitalist and Amazon investor John Doerr saw the value of the position and relayed it to Bezos “in response to Jeff’s ongoing quest for more efficiency and effectiveness,” says Doerr.

For much of Amazon’s first decade, Bezos’s shadows came and went quickly. In addition to Leschly, Danny Shader, the current CEO of cash payment startup PayNearMe, and Matt Williams, the former CEO of, both spent brief periods shadowing Bezos.

Then in 2003, the job grew more structured. Longtime Amazon executive Andy Jassy found himself without a role after an internal reorganization, so Bezos asked him to become his shadow. As I write in my book, The Everything Store: Jeff Bezos and the Age of Amazon, Jassy was conflicted because so many of the earlier shadows had left the company after failing to find a more permanent role. “I was flattered by the offer to work closely with Jeff but wasn’t initially excited about it, because I’d seen the way it had gone down before,” Jassy says. “I asked Jeff what success would look like. He said success would be if I got to know him and he got to know me and we built trust in each other.”

Bezos, who has a computer science and electrical engineering degree from Princeton, is extremely technical—the last thing he needs is an actual “technical assistant” to advise him on complex matters. Jassy redefined the position as a quasi-chief of staff, taking minutes at meetings, conferring with Bezos at the end of the day and making sure important things got done. After Jassy spent two years in the role, Bezos and Rick Dalzell, who was then Amazon’s chief technology officer, tapped him to run a nascent enterprise computing division called Amazon Web Services—an effort that blossomed under Jassy’s leadership and that will bring in nearly $4 billion in revenue this year, according to analyst estimates.

Jassy’s success in the role and ascension within Amazon helped increase the visibility and the desirability of the shadow position. Now even many of Amazon’s other senior executives, who sit on the company’s vaunted leadership counsel, the S Team, have their own shadows.

But it is the list of Jassy’s successors that should probably be tacked up on the bulletin boards of every headhunting firm in Silicon Valley. These are the executives who spent the most time with Jeff Bezos, who had the seat closest to his unconventional leadership style, and who have been trained in his peculiar way of thinking—to see only the big opportunities and to rarely get hindered by the obstacles. Here they are, for posterity:

Bezos’s League of Shadows:
Andy Jassy. 2003-4. Current role: senior vice president, Amazon Web Services.
Colin Bryar. 2004-05. Current role: retired from Amazon.
Ian Freed. 2005-06. Current role: vice president, Kindle.
Jim Adkins. 2006–07. Current role: vice president, Automotive and Home Improvement.
Amit Agarwal. 2007-09. Current role: vice president, International Expansion.
Greg Hart. 2009-11. vice president, Kindle.
Dilip Kumar. 2011-13. Current role: unknown.
Jay Marine. 2013-. Previous role: vice president, Kindle.

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