Pamela Cytron Of The Founders Arena On 5 Things You Need To Be A Highly Effective C-Level Leader Of A Fintech Company

An Interview With Kieran Powell

"Tell the truth fast. Truth builds trust and creates options. I’ve built my reputation on saying what others hesitate to say."

The fintech industry is rapidly evolving, blending technology and finance in innovative ways. This evolution demands leaders who are not only tech-savvy but also adept at navigating the unique challenges of the financial sector. Effective leadership in this dynamic environment is crucial for success. What does it take to excel as a C-Level leader in a fintech company? What are the skills, mindsets, and strategies required to lead a fintech organization to new heights? As part of this series, we had the pleasure of interviewing Pamela Cytron.

Pamela Cytron is president of the Founders Arena WealthTech Accelerator. She is an award-winning technology entrepreneur and strategic advisor with expertise in financial services, data intelligence, blockchain, privacy, and regulations. She has successfully grown start-ups and optimized revenue growth with innovative strategies while prioritizing the customer experience. Pam is a thought leader in data transparency and innovation, passionate about using technology for the greater good. She has received recognition for her leadership and serves non-profits at local, state, and national levels.

Thank you so much for your time! I know that you are a very busy person. Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I didn’t have a polished plan or a safety net. At 18, I found myself working at a small fintech company in Chicago called Catalytis, which later became the first fintech acquisition by SunGard. I started in sales, making cold calls, smiling and dialing, learning the business one conversation at a time. It was raw and unglamorous, but it was real.

What I lacked in experience, I made up for in persistence. My lack of fear wasn’t bravery, it was simply not knowing any better, and that turned out to be an advantage. When you don’t know the “rules,” you aren’t limited by them. I showed up every day, under pressure, learning in real time. That discipline of showing up consistently, regardless of circumstances, shaped everything that followed in my career.

Can you tell us what lesson you learned from that?

Starting in telemarketing was one of the toughest and most valuable experiences of my life. You learn to handle rejection, often hearing 50 “no’s” before getting to a “yes.” That forced me to toughen up quickly. It also taught me how to listen deeply, pick up on nuance, and build trust in under a minute.

Those skills became the foundation for how I sell, how I lead, and how I build. The bigger lesson was that you don’t need to have it all figured out. What matters is consistently showing up with purpose. Persistence, combined with curiosity and the ability to keep moving forward, becomes your competitive edge.

Are you working on any exciting new projects now? How do you think that will help people?

Yes, and this one is deeply personal. After navigating serious health challenges, I began to see the cracks in our systems in a very human way. Too often, the structures we rely on don’t serve us when life hits hardest.

I’m now combining decades of experience with advances in AI and data to create a new health and wellness company. It’s still in stealth, so can’t reveal the name yet, but the goal is to build smarter, more compassionate systems that center on people, not just processes. When you’ve lived through the system’s shortcomings yourself, you don’t just see an opportunity to innovate — you feel a responsibility to fix it.

What strategies do you use to maintain team morale and productivity during such times?

Clarity and transparency are everything. People can handle challenges and pivots, but what they can’t handle is uncertainty or spin. I believe in telling the truth fast, whether it’s good, bad, or messy.

That level of openness creates trust. It gives people the real context they need to focus on solving problems instead of guessing what’s happening behind the scenes. I also check in regularly, not just on performance, but on how people are actually doing. Morale and productivity come from consistency, honesty, and the assurance that leadership is paying attention.

How do you come up with goals for your area of responsibility within the organization?

I always start with impact. What problem are we solving, and who are we solving it for? From there, I reverse-engineer the goals to ensure they are purposeful, realistic, and measurable.

I also believe goals should be co-created. When the team is part of shaping the roadmap, they feel more ownership and accountability in achieving it. And I keep the focus tight. If a goal doesn’t directly move the needle, we don’t waste time on it.

How do you manage reporting to your board?

In early-stage companies, board meetings should be about strategy, not theater. I approach them as working sessions. I come with clarity on where we are, what’s working, what friction points exist, and what’s needed to move forward.

The right board adds value by engaging, challenging, and bringing stage-relevant experience. That’s why selecting the right members at the right time is so critical. My style is direct, transparent, and focused on outcomes. The objective isn’t to impress — it’s to progress.

Do you have any specific strategies that you use to manage your teams?

I see a clear distinction between managing and leading. I’ll admit I’m not a traditional manager. I don’t micromanage, and I don’t hand-hold. My strength is leadership — bringing clarity, urgency, and vision to the team.

I focus on hiring smart, self-directed people who are aligned with the mission. My role is to set the pace, clear obstacles, and maintain momentum. They trust me to create space for them to succeed, and I trust them to deliver. That mutual respect allows us to move quickly without falling into chaos.

Can you describe a customer-centric initiative you spearheaded at your company/firm and the impact it had on your business?

I believe every initiative should be customer-centric. One example was when I led the redesign of our enterprise onboarding process. It was fragmented, and clients were frustrated. We mapped every touchpoint, identified friction, and rebuilt it around clarity, speed, and trust. The impact was significant: higher retention, more referrals, and a more motivated internal team.

But customer focus isn’t about one project — it’s a philosophy. I still maintain relationships with customers from 40 years ago, which speaks to the power of trust. In one instance, I was brought into a major project that was failing. What turned it around wasn’t a new feature. It was tough, honest conversations and a mutual commitment to get it right. That’s what true customer-centricity looks like.

How do you approach risk assessment in your role, and can you give an example of a tough decision you made that involved a significant risk?

I evaluate risk through three lenses: reputation, relevance, and long-term impact. Not every risk is equal. Some financial risks are recoverable, but anything that compromises trust or values deserves immediate attention.

One of the toughest calls I made was walking away from a major partnership that looked excellent on paper but clashed with our principles around data integrity. It wasn’t easy — we needed that deal — but protecting the long-term mission and our credibility mattered more. In hindsight, it was the best decision we could have made.

What are the “5 Things You Need To Be A Highly Effective C-Level Leader Of A Fintech Company?” How have these 5 things impacted your work or your career? Please share a story or an example for each.

1. Tell the truth fast.

Truth builds trust and creates options. I’ve built my reputation on saying what others hesitate to say.

2. Execution over ego.

Ideas are meaningless without execution. Leadership is about ensuring the right person carries the ball across the finish line, even if it isn’t you.

3. Know when to walk.

Leadership means making hard decisions, including walking away from deals, partnerships, or even teams that don’t align with your mission.

4. Build trust faster than you scale.

In fintech, speed matters, but trust matters more. Growth without trust collapses quickly.

5. Don’t confuse busy with productive.

Impact matters more than activity. A lean, focused team that delivers will always outperform a bloated team that spins.

What do you believe are the key trends that will shape the future of the fintech or wealthtech industry?

Over the decades, I’ve witnessed true industry shifts: the rise of the internet, the outsourcing movement, SaaS, and the strategic use of data. Now we’re entering the AI era, but the reality is that AI is only as strong as the data behind it. Without authentic, quality data, AI is simply noise.

Looking ahead, I believe the biggest change will be how we define “wealth.” Wealth has traditionally meant exclusivity, but for most people it’s about freedom, opportunity, and security. The future will belong to companies that recognize this broader definition and make access more inclusive.

How are you adapting to these trends, and what role do you see your leadership playing in this adaptation?

I don’t chase trends — I interrogate them. I ask: Is this real? Is it useful? Does it serve the customer or just the hype cycle?

My leadership is grounded in clarity, consistency, and conviction. I don’t rush to appear agile. I make sure the team understands why we are making a move and how it connects to our mission.

With AI, data, and regulatory shifts, my role is to cut through the noise, protect what matters, and move forward with purpose.

If you could start a movement that would bring the most amount of good to the most amount of people, what would that be?

It would be about redefining our relationship with data. I’ve long advocated for #Data4Good because I’ve seen firsthand what happens when data is misused, manipulated, or misunderstood.

The goal isn’t more data, it’s better data. Data that is structured, ethical, private, and human-centered. Data literacy should be taught early, alongside math and reading. Privacy shouldn’t be a premium feature — it should be a foundation.

If we build systems rooted in transparency, accountability, and integrity, we create technology people can truly trust. Without that, nothing else matters.

How can our readers further follow your work online?

The best way is through LinkedIn and The Founders Arena. I focus on building more than broadcasting, but when I have something worth sharing, that’s where you’ll find it.

This was very inspiring. Thank you so much for joining us!