Meet Amazon’s new retail CEO: An ‘introverted big thinker’ with a track record of creative ideas that often fail to pan out

From at least 2015, Doug Herrington, who became Amazon’s new retail CEO last month, pushed the idea of launching an online-pharmacy business to the company’s senior leadership team, including founder Jeff Bezos. 

He would argue pharmacy was another large market bogged down by inefficiencies and pitched an online service that could quickly deliver prescription medications, according to people familiar with the matter. At one point, his team even drew up potential partnerships with Pfizer and Johnson & Johnson to help screen for counterfeit products, as Insider previously reported.

In those meetings, other participants would often lean in to hear Herrington talk because he spoke in such a low voice, one of the people said. Bezos, who was a fan of Herrington’s entrepreneurial streak, one former direct report said, bought into the idea, approving the $750 million Pillpack acquisition in 2018.

But four years after buying Pillpack, which was later rebranded as Amazon Pharmacy, Amazon is struggling to add new customers to its prescription business, according to people familiar with the team. Some say it’s emblematic of Herrington’s work at Amazon: big, bold ideas with mixed results.

Herrington’s performance will now come under greater scrutiny following his promotion last month to the most senior retail executive job, formally called CEO of Worldwide Amazon Stores. The move catapults the soft-spoken, 17-year company veteran with a penchant for creative thinking into the spotlight, at a time when the giant retailer faces slowing growth, an unsettled workforce, and a hostile regulatory environment.

His character and track record is an indication that Amazon is betting on a leader with a decidedly different profile than other executives that made it to the top. 

Herrington is known for being quiet and “introverted,” and more likely to be found at a chess club than a football game, according to people familiar with his work. He also lacks a giant success story on his résumé. While he’s responsible for helping grow Amazon’s retail business, which sold an estimated $600 billion worth of products last year, his big ideas for the grocery and private labels have not found any smash-hit success so far.

Meanwhile, Andy Jassy, who took over for Bezos as Amazon’s CEO last year, is known for using his overbearing micromanagement skills to build the $60 billion Amazon Web Services cloud empire from the ground up. Dave Clark, Herrington’s predecessor, is a famously demanding leader who created a hugely successful in-house shipping and logistics network at Amazon. 

“I love Doug — he’s a big thinker,” a former executive familiar with Herrington’s work told Insider. “But it’s not clear if there’s been a really big win in any of those areas. There are whispers of ‘show me the money.'”

Amazon’s spokesperson declined to provide a statement for this story.

‘Most enthusiastic guinea pig’

Herrington, 55, spent almost his entire career in the retail space. After graduating from Harvard Business School, Herrington worked as a partner in the retail, consumer products, and media group at the consulting firm Booz Allen Hamilton, according to his Linkedin page.

Then he went to Webvan in 1998, the high-profile grocery-delivery startup that famously went bust during the dot-com bubble. 

In 2005, he joined Amazon and spent all of his time on the consumables business, which oversees the company’s marketplace and retail products. He worked his way up to join the S-team in 2011, Amazon’s top decision-making council, which at the time had only about a dozen members. 

In the run-up to Amazon’s 2017 acquisition of Whole Foods, Herrington was a strong advocate for the deal, one former colleague said. 

Amazon Fresh store London, UK

Herrington is considered the founder of Amazon’s Fresh grocery business.

Grace Dean/Insider

Part of Herrington’s success at Amazon has to do with his ability to pursue ambitious ideas. He’s considered the de facto founder of Amazon’s Fresh grocery segment, and ran other major projects, like its private-label business and a task force to catch counterfeit sellers. More recently, he oversaw the launch of Buy with Prime, a new service that is going after Shopify’s turf.

“If you’re at Amazon, one of your biggest risks is that you’re not taking enough risks,” another person familiar with Herrington’s work said. “I love Doug because he’s unafraid to go after these bigger spaces.”

But many of Herrington’s initiatives still remain works in progress, and some he’s championed, like the questionable Dash button, are already dead. 

Though Herrington hasn’t directly managed it in recent years, Amazon’s Fresh grocery business accounts for a tiny sliver of the market, even after spending over 15 years in the space and billions of dollars in investments, including $13 billion to buy Whole Foods. As of March, Amazon and Whole Foods accounted for just 1.6% and 1.3% of the US grocery market, respectively, falling way behind Walmart’s 21.3% share and Kroger’s 10.2%, according to the research firm Numerator. 

And it still hasn’t figured out a way to sell groceries profitably. An internal financial report, reviewed by Insider, shows Amazon’s physical stores and grocery business recorded an operating loss of $1.1 billion in the first quarter. The grocery business itself, excluding ad-related revenues, generated about $900 million in first-quarter sales, one person said.

With Herrington’s promotion, Amazon will likely double down on growing its grocery business going forward, people who worked close to Herrington said.

On the marketplace side, Herrington’s team is still grappling with the counterfeit problem, despite years of work to mitigate it. Amazon launched a series of projects to stem the issue in recent years, including a new Counterfeit Crimes Unit. In 2021, Amazon spent more than $900 million on anti-counterfeit efforts and stopped more than 2.5 million fraudulent accounts, a company report said.

Herrington was an ardent evangelist for Amazon’s private-label initiative, and his team developed in-house products across dozens of categories from household goods to supplements. A former member of that team said Herrington was constantly calling colleagues into his office to try snacks and energy bars. He was the most enthusiastic guinea pig, they said, often wearing clothing and staples like socks for testing.

“Doug is strangely collaborative for Amazon,” said the same former colleague. “He likes an engaging meeting. He likes to bring people into the conversation.”

In a rare appearance at a company event in 2017, Herrington told employees that Amazon launched its private-label business in part to solve the counterfeit issue. He said many of its private-label products, like batteries, conduct more robust testing and go beyond industry standards to ensure consumer safety, according to a recording of the meeting reviewed by Insider.

“We’ve ended up delivering a better product and one that gives customers a lot more comfort about it,” Herrington said.

Still, Amazon’s private-label business has been riddled with problems in recent years. The unit was accused of using proprietary data to copy competing products sold on Amazon’s marketplace, The Wall Street Journal reported, sparking an antitrust investigation into the company’s business practices. And even after launching hundreds of its own private-label brands, ranging from underwear to vitamins, they still only account for 1% of Amazon’s total sales, the company says.

Jeff Bezos is seen talking through a screen hanging on the wall of the Rayburn House office Building on Capitol Hill.

Jeff Bezos testifying before the House Judiciary Subcommittee on Antitrust, Commercial and Administrative Law on July 29, 2020.

Mandel Ngan/Pool via REUTERS

Herrington is also known for his out-of-the-box thinking. He was a strong advocate for the Treasure Truck, a bizarre blue truck that drives around cities to sell limited-quantity products, such as inflatable paddleboards and 24-ounce porterhouse steaks. While the truck added some fun and engagement with customers, it has yet to drive huge revenue to Amazon, a person familiar with the business said.

Internally, Herrington is famous for a 2012 presentation he gave to the leadership team titled “Amazon’s future is CRaP.” In his memo, Herrington argued that Amazon had to sell CRaP products — CRaP stands for “can’t realize a profit” and includes low-margin items like grocery items — more profitably if it wanted to compete with the world’s largest brick-and-mortar retailers, which rely on the sales of frequently shopped, low-priced products to gain market share. Brad Stone reported on Herrington’s presentation in his book, “Amazon Unbound.” 

“You can credit him for people buying toothpaste on Amazon,” one person familiar with the presentation said of Herrington. 

Some executives defend Herrington’s track record. His teams have always had to compete in established categories, like groceries, apparel, and pharmaceuticals, making it hard to scale against large incumbents in a short period of time. He has also been a key member of Amazon’s market-leading e-commerce business since 2005, which now accounts for almost 40% of the US market. Some of his other bets, like Amazon’s business marketplace, reached $25 billion in annualized sales last year. It’s why Amazon continues to pour money into his teams and give long runways to prove themselves.

“It’s all share of wallet,” one of the people said. “Doug has owned the North American business, where like 100 million households are already Prime subscribers, so the only way to keep growing is to find more things to sell them that they already buy.”

Dave Clark’s opposite

Amazon’s retail business is moving into a new phase in which the priorities are somewhat ambiguous. The demand boom of the pandemic is over, and the company needs to find some form of equilibrium. Herrington’s rise may be evidence that a product-obsessed, big-ideas man — essentially the opposite of the operation-minded Clark — is what Jassy thinks the company needs.

Almost everyone who has worked with Herrington says he’s “universally liked” by his colleagues. A fan of no-show socks, Warby Parker glasses, and Allbirds shoes, he also adheres to the classic Amazon executive look. Often, he can be found carrying a bag of Cheez-It crackers.

In some ways, the mild-mannered Herrington is a rarity in Amazon’s hard-charging culture, people said, and a complete turnabout from his predecessor Clark, whom one person described as “soulless” and “ruthless” in his interactions with other colleagues.

But Herrington’s soft-spokenness masks his sharp business acumen, people say. In meetings, he likes to let others speak first, often buying time to collect his thoughts before speaking. Instead of confronting others, he often asks simple, innocent-sounding questions that gradually expose a bluff, one of the people said.

“I’ve never heard of anyone being intimidated by him,” one person who worked with Herrington said. “It’s all implied.”

Amazon retail CEO Dave Clark stands in front of a Prime delivery van

Herrington replaced Dave Clark, who built Amazon’s logistics business.


It’s unclear how Herrington’s even-keeled demeanor will translate in his new role. Many of his direct reports are type-A personalities who are used to working under the more flamboyant Clark. One person said Herrington struggles to get out in front to motivate others and prefers to lean on his direct reports to lead their respective areas. (Another person described this as a “collaborative” leadership style.)  

Adding to his challenges is the need to manage the logistics side of Amazon’s retail business, in which he has little experience. And unlike Clark, who was given plenty of time to prepare for the retail CEO role, Herrington was abruptly thrust into the job, a change one person called “the worst CEO transition I have ever seen.”

To help with the move, Herrington appointed longtime Amazon executive John Felton as the operations chief, to oversee all of the shipping and warehouse networks and report directly to him. In his first email to his team, reviewed by Insider, Herrington underscored his work with Felton’s team as a top priority.

“I’m especially looking forward to working more closely with our Operations teams,” the email said.

Herrington never seems to tire of working at an idea he believes in, said one former colleague. Amazon Fresh, private label, subscribe and save, Amazon pharmacy — they’re all far from hits and Herrington is just fine, they said. 

“His superpower is dealing with ambiguity and trying new things,” the same former colleague said. “I feel like his gift to me was the ability to sit in this big tangled mass of stuff and seem confident that we can still push it through.”

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Meet Amazon’s new retail CEO: An ‘introverted big thinker’ with a track record of creative ideas that often fail to pan out

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