Velera’s Chuck Fagan: A Career Retrospective

By John San Filippo

Over the years, Finopotamus has interviewed Velera CEO Chuck Fagan many times. However, on Mar. 25, Fagan announced that he is retiring at the end of September, passing the reins to Chief Administrative Officer Brian Caldarelli. That made the VeleraLIVE annual conference, running Apr.13-15, the last opportunity for an in-person interview.

Finopotamus sat down with Fagan to discuss his career, the lessons he’s learned along the way, and why he’s still passionate about the payments industry after nearly 40 years.

From Payments to Blue Suits and Back Again

Chuck Fagan (r) and John San Filippo: Their Final In-Person Interview

Fagan turned the clock back to 1988, when he started his journey at North Chesterfield, Va.-based Virginia Credit Union ($7.2 billion in assets; 491,000 members), which was a PSCU customer at the time.

Finopotamus asked how Fagan ended up in credit unions in the first place. He explained that fresh out of Longwood University with an economics and finance degree, he interviewed twice with Jane Watkins, who was then the credit union’s CFO, but was later named CEO. Watkins extended an offer for Fagan to become the payment system supervisor.

“I had one employee,” Fagan recalled, noting that payments back then were primarily ATMs, wire transfers, and ACH. He admitted that he never initially thought he would have a 40-year career in the sector. “The account I opened on my first day of employment at Virginia Credit Union is still the main financial account my wife and I use,” Fagan noted, adding that his long-term membership often surprises branch staff.

Finopotamus asked about Fagan’s brief eight-month stint working for Ross Perot’s Electronic Data Systems (EDS), where he managed relationships with financial institutions. Fagan laughed, recalling the rigid professional atmosphere and the literal catalog of approved clothing. “You had a catalog of blue suits and gray suits and white shirts and blue shirts, red ties and blue ties,” Fagan said.

“You Blew the Field Away”

Finopotamus next asked about the leap from EDS to PSCU. Fagan recounted flying to Florida to interview with the team and eventually meeting with Dave Serlo, PSCU’s CEO and first employee, as well as an eventual mentor to Fagan. After the interview, Serlo brought him into his office and asked how Fagan thought he had done.

“I said, ‘Dave, I’m familiar with the company and I just told it the way I believe PSCU supported me when I was at the credit union,’” Fagan said. Serlo’s response was immediate and definitive. “He said, ‘Well, you blew the rest of the field away and I’m offering you the job right now,’” Fagan recalled.

The offer was made on the spot. Fagan remembered the anxiety of that life-changing moment, standing at an airport payphone a short time later to call his wife, who was a fourth-grade teacher at the time. “We just got offered a job, but we have to move up near D.C.,” he told her. The 90-mile move from Richmond to Northern Virginia felt like moving to a different world, but it gave his wife the chance to stay home with their two children, then aged seven and three.

Taking on “This Internet Thing”

Three years into his tenure, Serlo approached Fagan with a new challenge. Serlo asked Fagan to take on “this internet thing,” believing it was going to “stick around.”

“He said, ‘I’ll pair you up with the technology team. You guys can figure out how we transform our business into the e-commerce and digital space.’” This assignment, which lasted several years, sparked Fagan’s desire to grow long-term with the company.

The Path Through Madison

When Serlo passed away on June 25, 2010, Fagan was not selected as his successor. “Over the course of the next roughly year [after Serlo’s passing], the board did their process and interviews and I didn't get the job. I was first loser, second place,” Fagan said with characteristic honesty.

Finopotamus questioned Fagan on how CUES entered the picture during that time. He explained that he was recruited to be their CEO and initially turned them down twice because he was “into payments.” However, the recruiter told him several people on the board knew him and refused to take no for an answer. Taking the role in Madison, Wis., (where he kept an apartment but did not move his family) forced him to master board management, build strategic plans, and handle a P&L—skills that rounded out his background for a future return to PSCU.

That opportunity presented itself on Feb. 9, 2015, recalled Fagan, when the PSCU board called and said, “We need to talk; we're making a change.”

“It was -26 degrees in Madison, and it was almost 80 degrees in Tampa [where PSCU was headquartered],” Fagan said. He officially started as CEO on April 20, 2015. He recalled his first all-hands meeting in St. Petersburg, where the enthusiasm in the room was palpable. He’s been at the helm ever since.

Leadership Lessons and Trimming Palm Trees

When Finopotamus asked who Fagan had learned his most important leadership lessons from, he pointed to Watkins, who gave him a stark piece of advice about the executive suite. “She told me that CEOs are seldom told the full truth,” Fagan said. “Find people that are willing to give it to you and keep them close by.”

He also discussed the nuances of board management, noting that a CEO works for the entire board, not just a single director. He admitted that it is often easy to focus on the one critical comment from a single director when the rest of the board is offering praise.

To illustrate how every role connects to the company’s success, Fagan shared a story about his facilities management team at Velera. He stated that if the palm trees aren’t trimmed or the building isn’t power-washed, it directly affects sales when a prospect visits. “I think our facilities management team plays into our sales,” Fagan said. “They play into our overall revenue growth, and they play into our net income.”

The Future: A 360-Degree View

Over the course of his career, Fagan has witnessed “sea change” shifts, particularly the introduction of Apple Pay just months before he became CEO. Fagan noted that while Google and others had wallets earlier, consumer trust wasn’t there yet. Now the phone has become the primary, secure method of transaction.

The conversation took a sobering turn when the topic of fraud came up. Fagan pointed out that fraud is projected to be the third-largest economy in the world by 2030, trailing only the U.S. and China, sparked largely by the pandemic. Noting the significance of fraud in the context of COVID, Fagan explained how the pandemic moved consumers right into the “fraudsters’ backyards” by accelerating online commerce.

As the conversation concluded, Fagan reflected on why companies like Amazon, Facebook, and Google all are vying for a place in the payments wallet. “They all want to be in payments,” Fagan said. “If Apple has a digital wallet and they understand how you use their products, but then they understand how people pay and how they use their money, they can get a 360 view of every single person that uses Apple.”

When Finopotamus asked if there was anything else Fagan wanted to add, he simply noted that it had been a pleasure to work in this industry and described his career as “living the dream.”