The American Express CEO defied haters who said he’d never have the top job—winning with millennials and Gen Z and trouncing the competition

Stephen Squeri appeared to check all the boxes as the next CEO of American Express. By 2016 he had spent three decades at the credit card colossus, reshaped tech operations, headed the corporate and merchant franchises, and orchestrated a spectacularly successful restructuring. But the Queens, N.Y., native had a giant liability in his quest to succeed the crisply tailored, cuff-link-sporting Ken Chenault: He didn’t dress like a Wall Street CEO.

A makeover helped get him the top job—and presaged the corporate makeover he has spent the past near decade enacting. Squeri has forged one of the top growth engines in financial services by luring lovers of luxe as never before, and trending exclusive and young in a big way. The success of Squeri’s highly original, against-the-tide strategy is something of a revelation. Though he heads the eighth largest U.S. player in financial services by market cap ($200 billion), and a fabled institution that ranks as Warren Buffett’s second largest holding at Berkshire Hathaway behind Apple, the Amex chief is little known to the public and keeps a far lower profile than, say, JPMorgan Chase’s Jamie Dimon or Goldman Sachs’ David Solomon. 

Yet surprisingly, since Squeri took the helm in early 2018, Amex boasts the highest returns among the largest U.S. commercial banks and payment providers. In that eight-year span, its stock has generated total yearly returns of 16.6%, a record that beats all its major peers and the benchmarks (save for Goldman Sachs which barely edges it out over that timeframe).

Squeri’s innovation: shifting sharply away from the “start folks cheap then upgrade them” policy that Amex and its competitors had long followed. He saw that affluent young people would happily pay up for premium cards, as long as the perks were right. “The reality is,” intones Squeri, uncorking one of his favorite phrases, “these Gen Z and millennials love premium, they love getting something that’s luxe. I viewed them as educated consumers who love luxury. They also love value. I said, ‘Wait a minute, these kids are smart.’” 

Amex’s Platinum Card “refresh” in September raised the fee from $695 to $895, but added sweeteners Squeri says are worth an extra $1,500 a year (including credits for Resy, Uber One, and hotel stays). The relaunch proved the most successful in Amex history, the company says. To wit: In the three weeks following the refresh, new account acquisitions on U.S. Platinum doubled, and retention rates have stayed high since, despite the fee increase.

Squeri has more than proved he can crack the upper echelons—both as a CEO and diviner of what high-earners want. Now, he just has to do what’s arguably even harder: keep those millions of millennials and Gen Zers happy and charging against the backdrop of an economy where everything is highly uncertain.

It’s a matter of pride that some of his best ideas come not from surveys or focus groups but especially from surveying what his own kids and their friends are doing. How did he glean that the youthful and affluent would flock to Platinum? “I just looked at my own household,” he says. “I have four daughters. When they talk, I listen. They make me listen. They’re very value-conscious—it’s always about a deal. When my oldest graduated from college, she got a Platinum Card. She was traveling all over the country visiting friends and going to weddings. She told me she liked the lounge access, that she liked the Uber credits; she liked the early check-in and 4 p.m. checkout at the hotels. She went for the luxury stuff, not points, and it was the same for her friends.”

After a stint at consultancy Accenture, Squeri joined American Express in 1985 as a manager in the Travelers Cheque Group. Over the next 30 years, Squeri moved upward to bigger and bigger jobs, chiefly in tech operations and commercial cards. But at every level, he heard the same refrain: You’ve topped out.   Squeri turned all the negativity into a quest to prove the naysayers wrong. “I guess you could say I had a chip on my shoulder,” he allowed in a 2024 podcast. “It’s served me well.”

Still, Squeri partly credited moving up at all to strenuous effort to burnish his homespun persona. Long before refilling his closets, “I was told, early in my career, ‘English is your second language,’” he declares. “I grew up speaking English, but I didn’t speak the ‘goodly’ English. I didn’t use all the letters in the alphabet all the time, I spoke the way I spoke growing up.” So Squeri “voluntarily” took training in elocution. 

Squeri then recounts what must rank as one of the most surprising CEO succession dramas ever. The clear front-runner as Chenault’s successor was president Ed Gilligan, one of Squeri’s best friends and an executive whom he’d worked alongside in three different jobs. “I was planning on retiring at age 60 in 2018,” says Squeri. “Ken already told me he didn’t think I was going to be CEO, which was fine, because I had no aspirations to be CEO.” In May of 2015, Amex’s road map for leadership suddenly got shredded: On a corporate jet flying back from Tokyo, Gilligan suffered a fatal heart attack.

“We’d gone through the Global Financial Crisis, but we were still in recovery mode,” says Squeri. Then Amex’s largest partnership—the Costco card, which accounted for 8% of worldwide business—suddenly fell apart. Costco wanted Amex to accept an extremely low rate on the money folks spent at its stores, a shift that would have made that business uneconomical. Costco went with Citi instead, and they remain partners to this day. Suddenly, Amex needed a mammoth restructuring initiative, in part to offset all the lost sales. 

To make matters worse, the introduction of the Chase Sapphire Reserve card in mid-2016 posed a big threat to the supremacy of the Platinum Card, then sorely in need of a refresh. Chenault assigned the crisis management role to Squeri. 

Chenault, renowned for his understated demeanor, then suggested that despite his strong endorsement, Squeri could face significant pushback. “Ken said, ‘We have some work to do with the board,’” Squeri recounts, and perhaps recalling the incident involving the Jets jersey asked his boss, “How many directors are there?” Chenault said, “Fifteen.” Asked how many Squeri had to convince, Chenault responded, “Fourteen.”

“The board saw this inside guy who was focused on cost reduction,” says Squeri. “They didn’t really see me as someone who could shape strategy or be good externally with partners.” Squeri entered what he calls a “speed dating” process with directors. “Some it took two times, some it took three times, and one it took four times,” he notes.

Squeri won the job and embarked on his daring road map: Doubling down on premium and courting the young and affluent. He also pledged a “revenue first” enterprise that made top-line expansion the leading priority.

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