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From Cracker Barrel to Boeing, Companies Are Turning to Retired CEOs

Perhaps 70 is the new 50 when boards are looking for veteran executives to stabilize a company.

Published on: Jul 28, 2026, 22:44:40 IST
WSJ
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In January, a headhunter from search firm Spencer Stuart started calling restaurant industry executives with a proposition: Would you come to Cracker Barrel as the next CEO?

PREMIUMRocking chairs are displayed for sale at a Cracker Barrel. The chain just hired a former restaurant executive as its next CEO.
Rocking chairs are displayed for sale at a Cracker Barrel. The chain just hired a former restaurant executive as its next CEO.

Cracker Barrel’s decision to select a 69-year-old former restaurant executive to lead the chain highlights the emerging practice of boards calling in retired chief executives from the sidelines to help engineer high-profile turnarounds.

The family-dining chain’s board and its current Gen X CEO had agreed that they would work together to look for

David Deno, who retired from Bloomin’ Brands, is taking over Cracker Barrel.

He steps into Cracker Barrel at an unusual moment. For much of the past year, the company has attempted to move on after efforts to modernize the chain backfired. Cracker Barrel’s outgoing CEO, Julie Masino, 55 years old, sought to update the chain’s look and menu to reach a younger audience.

The moves alienated some, including President Trump, with many arguing that the chain was abandoning its country heritage. Cracker Barrel later reversed the change and, more recently, the company’s stock had been rising.

The decision to recruit a new CEO is meant to reassure investors, management specialists said, though the bench of potential executives who carry both industry experience and trust on Wall Street is small.

Chart

“When all of these factors are taken into account, then the age of a candidate becomes kind of secondary because you’re dealing with a limited pool of candidates,” Tonello said.

Cracker Barrel is paying Deno $465,000 for relocation expenses to Nashville, Tenn., as well as providing a corporate apartment and twice monthly trips back to his home in St. Petersburg, Fla. for up to six months. His annual salary will be $1 million. Masino stands to collect $4.6 million in exit payments over two years, filings show.

Some CEOs say it takes some convincing to get them to give up their retirement. Before former PayPal CEO Dan Schulman became the CEO of Verizon last year, he was living on a ranch in Montana, riding horses daily while also moving cattle and thinking about beef prices.

“I was extremely happily retired, I will say. And I felt like I was a role model for retirement,” Schulman, now 68 years old, said at a Wall Street Journal event.

Schulman had been on Verizon’s board for years, and saw the company at an inflection point. “I also felt that the company had the ability to make that pivot,” he said last year. “If I didn’t feel that, I wouldn’t have taken the job.”

Dan Schulman went from being ‘happily retired’ to Verizon’s CEO.

Boeing, meanwhile, extended its mandatory retirement age when it appointed then 64-year-old Kelly Ortberg as CEO in 2024. Ortberg ran one of Boeing’s big suppliers, Rockwell Collins, until 2018, when it then merged with another aerospace manufacturer and eventually ended up part of RTX. He retired in 2021 but remained on the RTX board.

Jo-Ellen Pozner, an associate professor of management at Santa Clara University, said there tend to be two types of retired CEOs who make a comeback: those who remain active in business—either through board service or advisory roles—and those who simply realize they have little to do now that they are no longer running a company.

“There are some retired top executives who just have nothing else going on,” Pozner said. “They’re bored, and they don’t have anyone telling them how great they are all the time.”

The results of experienced CEOs tend to vary. Research published by Spencer Stuart in 2020 showed that, while nearly all of the experienced CEOs outperformed the market in their first role, only about 40% managed to do the same in subsequent positions.

The challenges in transforming Cracker Barrel are also great, restaurant-industry executives and management specialists said. “I don’t know whether he’s going to find a magic formula because it’s unclear if there is a magic formula,” Pozner said of Deno.

At Bloomin’ Brands, Deno rose to the top job after serving for years as the company’s chief financial officer. He guided the company through the pandemic and made a then-prescient call to not furlough employees during the earliest days of Covid, helping restaurants to recover more quickly. The company’s stock, though, was roughly flat during his tenure.

In an interview at the University of Michigan in 2024, Deno said he saw the job of a CEO as mostly focusing on culture. “This shocks people,” he said. “I probably spend 60% of my time on culture and leadership and people selection.”

He added: “If I don’t have the right people working for me, I’m dead.”

Write to Chip Cutter at chip.cutter@wsj.com and Heather Haddon at heather.haddon@wsj.com

In January, a headhunter from search firm Spencer Stuart started calling restaurant industry executives with a proposition: Would you come to Cracker Barrel as the next CEO?

PREMIUMRocking chairs are displayed for sale at a Cracker Barrel. The chain just hired a former restaurant executive as its next CEO.
Rocking chairs are displayed for sale at a Cracker Barrel. The chain just hired a former restaurant executive as its next CEO.

Cracker Barrel’s decision to select a 69-year-old former restaurant executive to lead the chain highlights the emerging practice of boards calling in retired chief executives from the sidelines to help engineer high-profile turnarounds.

The family-dining chain’s board and its current Gen X CEO had agreed that they would work together to look for her replacement after an uproar over branding changes caused the chain’s sales to plunge, according to people familiar with the search.

In recent years, Boeing, Verizon Communications and others have all chosen once-retired CEOs. An established executive brings instant credibility and experience to a role, governance specialists say, even if research suggests the performance of second-act CEOs tends to be mixed.

For the executives themselves, returning to the corner office often holds appeal, allowing them to dig into new business problems—while enjoying the perks and power of running a large company again.

“I’m not really sure there’s such a thing as a retired CEO in the U.S.,” said Matteo Tonello, head of data benchmarking and analytics at the Conference Board. “In this country, CEOs don’t really retire, they just become professional directors.”

Some, then, leave board work and move back into the top job.

Cracker Barrel’s new leader, David Deno, served as the CEO of Outback Steakhouse parent Bloomin’ Brands from 2019 to 2024. After he retired from Bloomin’ in 2024, he then served on the boards of Krispy Kreme and Panera Brands.

David Deno, who retired from Bloomin’ Brands, is taking over Cracker Barrel.

He steps into Cracker Barrel at an unusual moment. For much of the past year, the company has attempted to move on after efforts to modernize the chain backfired. Cracker Barrel’s outgoing CEO, Julie Masino, 55 years old, sought to update the chain’s look and menu to reach a younger audience.

The moves alienated some, including President Trump, with many arguing that the chain was abandoning its country heritage. Cracker Barrel later reversed the change and, more recently, the company’s stock had been rising.

The decision to recruit a new CEO is meant to reassure investors, management specialists said, though the bench of potential executives who carry both industry experience and trust on Wall Street is small.

Chart

“When all of these factors are taken into account, then the age of a candidate becomes kind of secondary because you’re dealing with a limited pool of candidates,” Tonello said.

Cracker Barrel is paying Deno $465,000 for relocation expenses to Nashville, Tenn., as well as providing a corporate apartment and twice monthly trips back to his home in St. Petersburg, Fla. for up to six months. His annual salary will be $1 million. Masino stands to collect $4.6 million in exit payments over two years, filings show.

Some CEOs say it takes some convincing to get them to give up their retirement. Before former PayPal CEO Dan Schulman became the CEO of Verizon last year, he was living on a ranch in Montana, riding horses daily while also moving cattle and thinking about beef prices.

“I was extremely happily retired, I will say. And I felt like I was a role model for retirement,” Schulman, now 68 years old, said at a Wall Street Journal event.

Schulman had been on Verizon’s board for years, and saw the company at an inflection point. “I also felt that the company had the ability to make that pivot,” he said last year. “If I didn’t feel that, I wouldn’t have taken the job.”

Dan Schulman went from being ‘happily retired’ to Verizon’s CEO.

Boeing, meanwhile, extended its mandatory retirement age when it appointed then 64-year-old Kelly Ortberg as CEO in 2024. Ortberg ran one of Boeing’s big suppliers, Rockwell Collins, until 2018, when it then merged with another aerospace manufacturer and eventually ended up part of RTX. He retired in 2021 but remained on the RTX board.

Jo-Ellen Pozner, an associate professor of management at Santa Clara University, said there tend to be two types of retired CEOs who make a comeback: those who remain active in business—either through board service or advisory roles—and those who simply realize they have little to do now that they are no longer running a company.

“There are some retired top executives who just have nothing else going on,” Pozner said. “They’re bored, and they don’t have anyone telling them how great they are all the time.”

The results of experienced CEOs tend to vary. Research published by Spencer Stuart in 2020 showed that, while nearly all of the experienced CEOs outperformed the market in their first role, only about 40% managed to do the same in subsequent positions.

The challenges in transforming Cracker Barrel are also great, restaurant-industry executives and management specialists said. “I don’t know whether he’s going to find a magic formula because it’s unclear if there is a magic formula,” Pozner said of Deno.

At Bloomin’ Brands, Deno rose to the top job after serving for years as the company’s chief financial officer. He guided the company through the pandemic and made a then-prescient call to not furlough employees during the earliest days of Covid, helping restaurants to recover more quickly. The company’s stock, though, was roughly flat during his tenure.

In an interview at the University of Michigan in 2024, Deno said he saw the job of a CEO as mostly focusing on culture. “This shocks people,” he said. “I probably spend 60% of my time on culture and leadership and people selection.”

He added: “If I don’t have the right people working for me, I’m dead.”

Write to Chip Cutter at chip.cutter@wsj.com and Heather Haddon at heather.haddon@wsj.com

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