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Fortune
Fortune
Sheryl Estrada

USAA's CFO joined the company as an intern. Here's how his 20-year journey led to the C-suite

Brett Seybold (Credit: Courtesy of USAA)

Good morning. For some executives, reaching the CFO seat was an unexpected destination in their career journey. Meanwhile, others just knew that one day their resume would include the title of finance chief.

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

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