Amazon Consumer CEO Jeff Wilke at the 2017 GeekWire Summit. (GeekWire Photo / Dan DeLong)

Jeff Wilke, the flannel-wearing CEO of Amazon’s vast consumer business, has been described as a natural business leader and the most important executive at the company over the past decade. The 53-year-old Pittsburgh native also was viewed as the logical successor to Amazon founder Jeff Bezos.

So when Wilke last week announced his plans to retire in the first quarter of next year — an unexpected move that caught many Amazon watchers off guard — we naturally wondered: Who is next in line?

It’s a simple question, but the answers are as complex as Amazon itself.

To get a better sense of who may lead the sprawling empire of Amazon — a company that now touches everything from advertising to entertainment to logistics and cloud computing — we chatted with half a dozen former managers, executives and insiders. Most wanted to talk off the record, echoing the intense privacy that surrounds one of the world’s largest companies. Amazon declined to comment on its succession plans.

First, a quick caveat. There’s no indication that Jeff Bezos, at age 56, is ready to hand over the reins. In fact, COVID-19 is only driving Bezos to reimagine the company he started as a tiny online bookseller in a Bellevue home in 1994.

One former insider told us that Bezos is “very engaged” in building the business, and is especially interested in expanding the company’s reach into areas like healthcare and autonomous vehicles. “I don’t expect him to step down from CEO anytime soon,” this person said.

Even so, every large publicly-traded company — especially one with a $1.7 trillion market value — needs to be prepared for a future without its founder.

AWS CEO Andy Jassy at the 2019 re:Invent conference. (GeekWire Photo / Todd Bishop)

But there are some obvious choices for a successor among the company’s top executives: Amazon Web Services CEO Andy Jassy; Senior Vice President of Worldwide Business Development Jeff Blackburn (who is on a year-long sabbatical); and Dave Clark, the senior vice president of worldwide operations, who is taking over for Wilke.

It’s also worth looking at Amazon’s recently expanded 26-person “S-team,” the leadership group that drives key decisions for the company and includes executives who oversee business lines such as fulfillment, studios, fashion and delivery. The longer Bezos remains at the company, the more likely the reins could eventually be handed to someone who’s currently a newer member of that leadership team. That’s one reason why the growing (yet still minimal) gender and racial diversity among that group is notable.

For the time being, Jassy is the likely front runner for the CEO job, overseeing the enormously profitable cloud computing business.

One former Amazon manager noted that if you were to split Jeff Bezos in half you’d find the combination of Jeff Wilke — an “incredibly talented business executive” — and Andy Jassy — a Jeff Bezos “whisperer” who is the embodiment of Amazon’s 14 leadership principles.

In fact, those principles — frugality; thinking big; insisting on high standards; etc. — are so core to the success of Amazon that it’s highly unlikely that any future CEO would come from outside the organization.

In that regard, Amazon could (reluctantly) take a page from perhaps the most successful CEO transition of the past decade.

Bill Gates, Satya Nadella and Steve Ballmer at Microsoft in 2014. (Microsoft Photo)

When Satya Nadella was named CEO of Microsoft six years ago, very few had him on the short list of candidates. He’d never served as CEO, and he came from deep within the engineering ranks of a company that needed to refocus on its expertise in enterprise software and the cloud.

The internal pick was, by many measures, the right choice for Microsoft, just as Apple successfully transitioned to operating executive Tim Cook following the untimely death of co-founder Steve Jobs. Both Apple and Microsoft — who’ve grown significantly in recent years — looked internally for their next CEOs.

Of course, Amazon is a very different beast than Apple or Microsoft. But its culture does lend itself to picking an insider.

“There’s certainly bench strength,” said Dr. Bruce Avolio, a business professor at The University of Washington who specializes in strategic leadership. “Learning the culture and how different it is would be a challenge for somebody, especially given the up tempo of Amazon.”

Executives who succeed at Amazon tend to have long tenures — Jassy is in his 23rd year; CFO Brian Olsavsky is in his 18th year; and senior vice president and general counsel David Zapolsky is in his 21st year.

Amazon’s Dave Clark, now the new CEO of the company’s consumer business, at a 2018 event unveiling the company’s Delivery Service Partners program. (GeekWire Photo / Kurt Schlosser)

Clark, who worked as a junior high school music teacher for a year after college, has spent nearly all of his adult career at Amazon. The 47-year-old joined Amazon in 1999 after graduate school, and worked his way up the ladder, implementing robotics in fulfillment centers and overseeing the electrification of the company’s ever-expanding delivery fleet. (A good profile of Clark from Fortune magazine here).

Clark will have a big flannel to fill when Wilke — who for years celebrated front line Amazon workers by wearing flannel shirts during the fourth quarter — retires.

One former Amazon executive told GeekWire that Wilke was perhaps the most important executive in the entire organization for the past decade.

“He brought lean thinking into the organization, developed the category leader model and set Amazon up for the tremendous growth over last 10 years,” the former executive said.

A former general manager at Amazon noted that Wilke possessed a “weird combination” of being data-driven plus deep understanding of what it takes to motivate people.

“One of the things that makes Wilke very unique and special is his desire to understand the human algorithm, and what does it mean to organize and lead hundreds of thousands of individuals,” he said.

That softer skill will be hard to replace at a company like Amazon. And that’s why his departure left many wondering: Why leave?

If there is one magical attribute of Amazon, it is the company’s ability to keep the entrepreneurial flame burning even as it tops one million employees and nears $90 billion in quarterly sales. The next leader will embody that unusual characteristic, continuing to push the company into new areas — understanding how to quickly learn from failures and experimenting when the time is right. Of course, this focus on innovation will need to happen while balancing Amazon’s new-found power in the global economy.

Amazon could decide to find a CEO with international experience, since Dr. Avolio noted that they are still a U.S.-centric company which is “unusual for an organization that large.” That said, the company recently reached a milestone with a $345 million profit in its international business in the second quarter. Amazon has long lost money in its international e-commerce segment.

Succession is more than the name of an HBO drama. It’s one of the hardest things for a company to get right. And there is added complexity with a company of Amazon’s size, reach and — shall we say — uniqueness. (Or peculiarity, as people at the company would say.) And, of course, there is also the challenge of replacing a charismatic founder in Jeff Bezos.

In that regard, companies often look for successors who can help define a new age. Tim Cook brought complementary skills to Apple, just as Satya Nadella added a different style to Microsoft from the Steve Ballmer era. Amazon may look for that complementary person for its next leader, someone who is different from Bezos.

That’s often the better strategy for companies looking at succession.

“Otherwise, you are constantly being compared to the (founder),” said Avolio. “Organizations need different leaders in different periods of time.”

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