Helping build a professional baseball league where dancing is part of the job description would seem like a tough gig to outgrow.

After leading finance at the Savannah Bananas for four years, Tim Naddy was hungry for a bigger challenge. Once he deemed the financial infrastructure was ready for its next leader, he wanted another opportunity to use the operational skills he had developed along the way.

“I had more to offer,” Naddy told CFO Upside in a recent interview. “I wanted to use those muscles.”

His decision to leave for a variety of new roles reflects the widespread ambition among many CFOs around interest in having a combined finance and operating role. As automation frees up time in finance, many finance leaders now have unprecedented room to get involved in how their businesses run, and some want formal responsibility for the work they already help shape.

In places like midmarket and private equity-backed companies, where growth plans regularly pull finance leaders into operations, Naddy’s experience raises a familiar question: How do you keep growing once you’ve built a finance function that works?

By the time he left in August, the Bananas had grown from a regionally entertaining summer wood bat contender into a formidable, six-team-strong, entertainment juggernaut dubbed the Banana Ball Championship League, and Naddy said he felt confident his scalable financial infrastructure was ready for another leader to take it to the next level.

Yet, he yearned for roles with more room for strategy, creativity and business development. Those aren’t necessarily the calling cards of your average CFOs, but Naddy wanted to focus on what he enjoyed most about helping an organization grow: fostering relationships.

Leaving the Bunch

When Naddy first spoke with Bananas founder Jesse Cole about joining in 2022, the ambition to build a league caught his attention. He imagined a central operation supporting multiple teams and wanted to help develop it.

“I wanted to help build a league,” Naddy said, recalling his thinking. “This league mentality, I could get behind this.”

As that vision developed, finance stayed close to the work happening throughout the organization. Adding teams meant expanding the resources behind each show, including transportation and warehouse capacity. Naddy’s responsibilities grew with the business, allowing his experience to grow within quick-moving operational decisions that made hyperexpansion possible.

“Certainly my job was finance first,” he said. “But it was never just finance.”

In 2026, moving from four teams to six proved pivotal, as Naddy was able to substantially step up the resources needed to support the league. With that experience giving the organization a clearer understanding around the true labors of expansion, the next stage could be planned with the benefit of having already worked through the very real and foundational growing pains.

“Now [the league] can anticipate what it looks like if they’re going to have another two teams, and two more after that,” he said.

With what he called his “trained and accomplished team” in place keeping the league’s finance operations running smoothly, Naddy thought that this was the perfect time to hand things over to the next “potassium-crazed” financial leader.

“I feel like I was able to package up a well-oiled machine and confidently give it over to whoever the next person was going to be,” Naddy said.

Shop Talk and Pillow Talk

Years spent helping a business grow can give any CFO an appetite for greater operational responsibility or entrepreneurship.

In places like PE or the midmarket, that might mean taking ownership of an integration or pursuing that highly coveted combined CFO and COO role. Naddy’s experience, however, shows how that ambition can develop through work a finance leader naturally takes on along the way.

At the Bananas, he became involved in maintaining relationships between finance and the people around the organization. As the business expanded, he saw connections that some of the less experienced had not, so he pulled them into his orbit. “This is not a job that I was given,” Naddy said. “When you’re part of a young and growing team that is lacking certain skillsets, you step up and lead. I had to go grab it.”

That initiative gave him more opportunities to use skills he had developed throughout his career, particularly as a professor of entrepreneurial finance at the Savannah College of Art and Design. Explaining financial information, he said, requires him to understand the person across the table, and have an ability to empathize, so that the conversation has the most impact.

Over time, he said those interactions continued to reinforce how much he truly enjoyed the relationship-building side of leadership. “I really like bringing myself into alignment with [stakeholders] in a communications stance so that we can have really good, productive conversations about the business,” he said.

For a CFO seeking a change of pace, that ability can become especially valuable when taking on responsibility for work across departments. Familiarity with the numbers provides a foundation, but a good CFO knows it’s the part that entails communication with colleagues that provides a way to turn a data-driven decision into bold action.

At home, Naddy’s wife, Jennifer, who had also worked in merchandise sales on game days for the Bananas, noticed that he wanted a bit more opportunity to contribute to the bigger picture.

These late-night conversations helped him to better understand what he finds energizing in the business world and how he could best incorporate that in his next role. “I just wish I could do a little bit more,” he recalled telling her, a bit of pillow talk that may sound familiar to other finance leaders and their spouses.

Finance with Feelings: Among the work Naddy said he enjoyed most was helping the players manage six-figure earnings for the first time, many of whom were getting married, buying homes or starting families while playing on the team. “That’s the piece I miss the most,” he said. “The human connection with the guys because they’re wonderful, wonderful people.”