What lessons have fintech CEOs learned while mastering the art of leadership?

Writer’s note: This story is the first part of the series ‘The Journey to Leadership’ spotlighting six fintech CEOs and their individual journeys. The intention of this story isn’t to lay down a universal blueprint for becoming a superior CEO. After all, a) there’s no one-size-fits-all formula, and b) each leader’s path is subjective and distinctive. Instead, I aim to uncover the lessons learned by prominent leaders in the space, both seasoned and young, and how their experiences have molded their understanding of their capabilities and roles.

While induction sessions are common for other roles within a company, how does one go about learning the ins and outs of being a fintech CEO? Young CEOs are eager to seek advice and learn from seasoned leaders. Meanwhile, experienced ones recognize the importance of balancing external advice with their own experiences on this evolving journey. They understand that they alone can navigate their roles, shape their leadership style, and steer their companies.

Knowing when to accept advice and when to pause

“One of the most valuable lessons I’ve learned as Mercury’s CEO is that you should constantly seek the advice of others,” said Immad Akhund, CEO and co-founder of Mercury, a business and consumer banking startup.

However, Akhund underscores the importance of being discerning when it comes to seeking advice from the right person at the right moment. Seeking guidance from leaders who have already trodden a similar path but are a step ahead can be valuable.

“As CEO, you don’t have anyone from whom you can learn very easily. It’s your responsibility to source advice from the right people proactively. If you’re not doing that, you’re not learning,” said Akhund. “When you talk to people who are further along, you tap into things you don’t know and it helps you prepare for what’s next with your business and see around corners.”

Harnessing previous experiences to achieve favorable outcomes

Akhund has been Mercury’s CEO for nearly seven years, following an eight-and-a-half-year tenure in another CEO role. While some current CEOs bring prior CEO experience, others are relatively new to top leadership roles. Everett Cook, who has helmed business banking platform Rho as CEO for the past six years, transitioned from a role as a hedge fund analyst. This background has given him an atypical perspective on building a company. Drawing from his experience in markets and investing, he melds these skills together to make decisions for his company in his current capacity.

“Markets are fundamentally an ideas business – everyone has the same set of securities to invest in, so the only differentiator is the quality of your ideas and how well you size and manage your bets,” said Cook. “The biggest difference is that in markets, the execution of an idea is trivial, whereas in company building the execution is the hard part. But ideas still count and you still need to make good bets in order to win over the long run.”

What defines a good bet? Cook believes it boils down to understanding the dynamics of supply and demand. He stresses the importance of CEOs being aware of their position within the market cycles and managing accordingly.

Cook also learns from the markets the importance of accepting mistakes and maintaining emotional discipline. “You don’t have to be right all the time, but the expected value of your bets has to be positive over time,” he noted. “I think it’s similar for us — you want to carefully size and scale your investments according to the likelihood of success and your risk tolerance. Identifying winners and losers swiftly, cutting losses, and doubling down on successful ventures are crucial. And never get emotional about a trade.”

The significance of skill development in driving progress

Being receptive to acquiring and refining new skills over time can add another layer of expertise.

Stephany Kirkpatrick, the founder and CEO of Orum, an API integration for instant payouts, highlights the importance of skill development as an essential part of one’s career path before stepping into the role of CEO.

Prior to founding Orum, she worked at a financial planning startup. “Working for a female entrepreneur was truly inspiring. Being part of an early-stage company was an eye-opening experience,” said Kirkpatrick.

From that early career experience, she learned the value of growth – staying curious and seizing opportunities that foster learning and skill development. If an opportunity arises, step up; if there’s a chance to sit at the table, listen, absorb the discussions, and then share your insights.

Kirkpatrick believes that a crucial aspect of being a CEO and founder is becoming comfortable with risk and decision-making. Seeing the emergence of real-time payment networks, she recognized the potential but understood she was entering uncharted territory by building a technology company focused on faster payments. Transitioning from consumer to enterprise sales presented challenges, and institutions were wary of fraud risks when adopting instant payment rails.

“What I’ve learned is that you shouldn’t ignore risk or try to hide from it. By confronting it head-on and figuring out how to address it, you can transform it from a liability into an asset.”

Getting to the core of challenges

Some leaders have come to understand along their journey that leading a company involves identifying and understanding the root causes of challenges, as solutions and product development may not always be the only answers.

Michael Rangel, CEO of SMB banking platform Novo for eight and a half years, has learned the importance of prioritizing the problem over the solution. He emphasizes that solving the big problems becomes even more critical as the product team expands. With the addition of new members, there’s often a lack of deep understanding of the company’s goals, leading them to focus on building rather than understanding the underlying issues first.

“I’ve seen that people can focus more on building products that they believe are solutions, but not staying close enough to the customer and the problems they face,” he noted.

Clichéd but true: It all begins by understanding the vision and mission

CEOs with decades of experience and multiple ventures under their belt suggest that refining their leadership skills has involved beginning from the ground level to fully grasp the role.

Four-time founder Max Levchin, the CEO and co-founder of BNPL provider Affirm, and f co-founder of PayPal, emphasizes the importance of having a succinctly defined mission and a set of core values unique to the business. 

“Many decisions become straightforward when you have in black-and-white what you stand for, why you are here, and what you would or would not do, no matter the cost,” he said. “This clarity is crucial because as your organization scales to thousands of employees, you won’t always even be in the room to make those decisions. Establishing a system of values specific to your business will make tough decisions significantly easier.”

Clarity on the company’s mission and vision is also central to one of four principles Colin Walsh, CEO and founder of neobank Varo Bank, has learned and applied in his leadership role from his nearly two decades of experience prior to founding Varo Bank. 

His four core tenets include:

1. Consistent mission and vision alignment: Walsh highlights the importance of aligning investors, the board, employees, and stakeholders with the company’s vision and strategy for growth. This involves consistent and clear communication, relevant incentives, and tough decision-making, all while prioritizing profitability.
2. Financial discipline: “I’ve established a culture of financial discipline at Varo,” said Walsh. This means charting a clear path to profitability, making data-driven decisions on resource allocation, and avoiding excessive cash burn in the quest for growth at any cost.
3. Adaptability: Given the constantly evolving fintech landscape with new technologies, regulations, and economic conditions, Walsh believes CEOs must be flexible and willing to adjust strategies as necessary. What worked in the past may not be effective in a profitability-focused environment.
4. Operational efficiency: Under the pressure to achieve profitability, fintech CEOs can optimize their operations to maximize margins. 

What proves effective for one CEO and their company may not translate to another, but combining others’ experiences with self-reflection can lead to favorable outcomes.