I recently sat down with Brett Seybold, EVP and CFO of USAA, a financial services and insurance provider for the military community and their families. After more than two decades at the company, Seybold was promoted to CFO in July. 

At age 44, he is among the younger CFOs at Fortune 500 companies, where the average age for the position was 53 in 2024, according to S&P Global Market Intelligence data.

“I guess I’ve always been destined to work in finance,” Seybold told me. “From an early age, I knew I liked math. I remember my dad teaching me the power of compound interest sitting at a table, probably when I was in kindergarten.”

One of his father’s best friends was a banker. “I was always questioning what he did, and what it was like,” Seybold said. 

His curiosity eventually drove him to venture out far from home. “I got the hell out of Dodge…I actually grew up in Dodge City, Kansas,” he quipped.

After graduating from Kansas State University with a bachelor of science in finance, he moved to Texas for an opportunity at USAA. “I went from intern to CFO in 20 years,” Seybold said. 

Never get too comfortable

A private company, USAA ranks at No. 103 in the Fortune 500. For 2023, the company reported a net income of $1.2 billion and increased its net worth 6% year over year, reaching $29.1 billion. And revenues rose by 17% to $42.5 billion.

“Over the 20 years, I’ve had about 19 different configurations of responsibilities, even if they weren’t job title changes,” Seybold said. 

That all began when Seybold was hired for a full-time role at the company. He was placed in a rotation program for three years. During his second year, he was on the investment team. Every Friday, Seybold had to give a presentation to his team leader, who was also a professor, discussing what he learned during the week. 

“While it was excruciating, I knew that I was getting extra learning in that group,” he said. 

Leaders soon turned into trusted mentors at the company and would encourage him to try new roles, and even make lateral moves. But Seybold didn’t always agree at first.

Like when he was asked to make a move within the treasury department. “I told the treasurer at the time, ‘You know, I really like what I’m doing and I’m thinking about staying,’” he recalled. “But about two hours later, he told me I was moving.”

“They never let me get too comfortable, and at times challenged me to learn a new side of the business,” Seybold said. 

Paying it forward

USAA’s culture of continual learning is a part of its military heritage, Seybold said. For example, the legacy of the late Josue “Joe” Robles Jr., who served as a two-star general before joining the company, he said. Robles became the CFO and eventually was promoted to CEO, leading a significant period of growth for USAA. 

“He was passionate about giving people training and opportunities,” Seybold said. 

Over the years, Seybold held an array of leadership roles in finance like executive director of enterprise capital management and VP of FP&A and strategic solutions. However, taking on the additional role of chief transformation officer while he was corporate treasurer was a profound experience that helped prepare him for the CFO role. 

“It really expanded my brand, but also stretched my ability to influence the entire organization to go down a certain path,” he said. 

Another significant experience was as SVP and senior financial officer of property and casualty insurance, a large portion of USAA’s business. “I was advising the president and the board during a very critical time, which allowed me to show my strategic mindset,” Seybold said. 

Now as CFO with 1,110 people on his team, Seybold is paying it forward, encouraging others to learn and grow, he said. And that includes a big focus on using technology to reimagine all of the company’s processes for efficiency and an enhanced member experience, he added.

“If you do your job well, remain passionate about learning, and help others succeed, you’ll have a great career, without even needing to bounce around to different companies,” Seybold said. 

Have a good weekend.

Sheryl Estrada
sheryl.estrada@fortune.com

Leaderboard

Fortune 500 Power Moves

The Kroger Co. (No. 25) announced that David Kennerley will become CFO, effective April 3. Kennerley will join the supermarket giant on March 10 as senior vice president, while interim CFO Todd Foley continues through the end of Kroger’s fiscal year 2024 reporting cycle. Kennerley joins Kroger from PepsiCo, where he’s served as senior vice president and CFO for PepsiCo Europe since March 2020. He joined the company in 2001.  

Southwest Airlines (No. 159), announced that Tom Doxey will become EVP and CFO, effective March 10. Doxey most recently served as president of Breeze Airways. Before that, he held several leadership roles at United Airlines, including SVP of technical operations and CFO of operations. Doxey’s aviation career began in financial planning and fleet management roles at Allegiant Air and US Airways.

Every Friday morning, the weekly Fortune 500 Power Moves column tracks Fortune 500 company C-suite shifts—see the most recent edition. 

More notable moves this week

Bob Foster was promoted to CFO of Paycom Software, Inc. (NYSE: PAYC), effective Feb. 21. He succeeds Craig Boelte, who is retiring. Foster joined the company in 2022 to lead Paycom’s growth strategy and later served as EVP of accounting and finance. 

Robert (Bob) Gold was appointed CFO of Pitney Bowes Inc. (NYSE: PBI), a provider of SaaS shipping solutions and financial services, effective March 10. He will succeed Pitney Bowes veteran John Witek, who has served as the company’s interim CFO. Gold most recently served as EVP and CFO at EyeCare Partners. 

Chris Sasser was promoted to CFO of Tropical Smoothie Cafe, following the retirement of his predecessor. Sasser joined the company in 2019. He was most recently chief strategy officer. Before that, he was SVP of finance and analytics. 

Deepa Subramanian was named CFO of DailyPay, a work-tech platform. Ken Brause, who served as CFO since November 2023, has been appointed chief administrative officer. Subramanian most recently served as VP of corporate finance and investor relations at Uber Inc. Before that, she held the role of CFO for Uber’s Delivery (Eats) business.

Big Deal

It’s Valentine’s Day and consumers are expected to spend $27.5 billion this year, according to the annual survey by the National Retail Federation and Prosper Insights & Analytics. The amount is up from $25.8 billion in 2024 and slightly above the previous record of $27.4 billion set in 2020. Consumers plan to spend $188.81 on average on the holiday, up from $185.81 in 2024.

More shoppers plan to celebrate Valentine’s Day this year (56%), up from 53% in 2024. Another finding from the survey is men are more likely to celebrate this year with 55% saying they plan to participate in Valentine’s Day, up from 51% in 2024, according to NRF.

Going deeper

Here are four Fortune weekend reads:

“JPMorgan claims a millennial founder tricked them into buying her student loan startup. Now Charlie Javice is getting her day in court” by Luisa Beltran

“Rate cut hopes are fading fast as inflation data and record egg prices make ‘very uncomfortable’ reading for Jerome Powell” by Eleanor Pringle

“Family offices are booming: Inside the secretive finance centers that cater to billionaires like Jeff Bezos and the Walton family” by Alicia Adamczyk

“In a showdown of psychotherapists vs. ChatGPT, the latter wins, new study finds” by Beth Greenfield

Overheard

“Validating language between two people creates empathy and creates mutual respect. And when you have those two things, you’re more inclined to be magnetic towards one another.”

—Christina Eller, a psychotherapist, told Fortune in a discussion about six defining traits of the longest and healthiest marriages.