Eight months into his CFO role at Reltio, James Redfern still feels like he’s catching up. “I’ve made some progress, but I’m definitely not where I… need to get,” he tells us. That steep learning curve was exactly what drew him to the company.

Redfern didn’t find the Reltio opportunity through recruiters. Instead, it surfaced during a casual conversation with a mentor. “I was actually looking at something else,” he recalls. “And he said, ‘Oh, if you’re looking… I’m on the board of a company that’s looking for a CFO.’” That kind of personal connection—what Redfern calls “psychic safety”—has guided his last two career moves. It’s less about who you know casually, he tells us, and more about “people you actually have worked with.”

At Reltio, Redfern stepped out of his comfort zone. After years in application-layer software companies like Workday and PayScale, he shifted into deep IT infrastructure. Reltio’s platform ensures enterprise data is clean and consistent across systems—a need made more urgent by the rise of AI. “You need a reliable, unified view of your data,” he explains. “One customer equals one customer—not three different customers in three different systems.”

With 190 customers and $160 million in annual recurring revenue, Reltio works with some of the world’s largest enterprises. The company’s mission, Redfern tells us, is to replace legacy systems like Informatica and IBM with cloud-native data unification at scale.

For Redfern, the attraction wasn’t the title. It was the challenge. “This is the kind of journey I committed myself to,” he says.

Amanda Whalen’s first unit CFO role began with a question. “You’re not a finance technical person,” her company’s president told her, “but you’re the strongest leader on my team. Will you be willing to be the CFO and help me transform the finance function?” She accepted.

Over the following year, Whalen tells us, her team tackled three major initiatives: fixing broken cost accounting at a dairy plant, realigning sales incentives to drive margin, and overhauling the P&L reporting structure to match the new parent company’s expectations. The team was skeptical—“They said, ‘You’re crazy. There’s no way we can do that all in a year,’” she recalls. But they did. The business became 10% more profitable.

That experience, Whalen tells us, revealed finance as a powerful lever to drive business transformation—“You get to work with every function… It’s highly quantitative and analytical, and it involves working with a lot of really great people.”

Now CFO at Klaviyo, Whalen brings the same philosophy. In three years, the company more than doubled revenue and improved margins by 20 percentage points. She led Klaviyo’s IPO, expanding the company’s readiness across technical, strategic, and investor-facing dimensions. “It wasn’t just about getting ready to go public,” she says, “but about operating successfully as a public company for a long, long time.”

Whether transforming legacy operations or scaling a fast-growing SaaS firm, Whalen’s approach remains constant: think long-term, go deep into execution, and “be kind to your future self.”