Lessons from the frontlines: A woman's journey in payments and leadership

If you glance at my résumé, it might look like a straight path to the CFO seat. It wasn't. My career has been shaped less by a master plan and more by instability - economic, professional and personal. The common thread has been learning to adapt while staying focused and disciplined. 

I grew up in Sofia, Bulgaria, in the years after the fall of communism. By 1997, the country was in an economic tailspin. Hyperinflation wasn't something we read about - we lived it. Prices changed daily. Savings disappeared. Even a simple grocery run became a crash course in monetary instability.

At the time, I was studying law. As the crisis deepened, I helped organize student protests calling for reform. I remember standing outside parliament in the freezing cold realizing that change doesn't happen on its own. If you want it, you have to push for it.

Soon after, I won the U.S. green card lottery and moved to New York with $3,000 and a decision to start over - shifting from law to economics. At Columbia University, I was learning a new financial language while adjusting to a new country and culture. There was no safety net. Adaptability stopped being a personality trait and became a necessity.

That lesson came back again right after graduation. I landed an investment banking offer - only to have it rescinded when the market unexpectedly shifted. At the time, it felt devastating. In hindsight, it forced me to rethink what I actually wanted.

I took a short-term role helping a tech CEO prepare for a fundraising round, building the company's financial model. It was supposed to be temporary. But sitting inside the business, seeing how decisions were made and how strategy translated into numbers, changed something for me. I realized I didn't want to analyze companies from the outside. I wanted to help build them from the inside.

After a few detours - including FP&A and earning my MBA - I returned to tech, and ultimately fintech, where finance isn't a support function. It's part of what you're building.

In 2014, I joined Riskified shortly after its Series A as the first in-house finance hire. There were no systems, no long-term data sets, no established infrastructure. We built the basics from scratch - processes, reporting, KPIs - anything that would help us truly understand how the business was performing. Those early foundations made everything that followed possible.

Leading our IPO in 2021 put all of it to the test. We took the company public at the height of a global pandemic, which meant tossing out the standard playbook. Roadshows were virtual. Teams were distributed. What mattered most was staying disciplined while adapting to constant change. It reinforced a belief I hold strongly: effective leaders have to be flexible without losing focus. Leadership isn't about having every single answer - it's about maintaining clarity for your team when everything else feels uncertain.

Today, as CFO, I carry that same mindset with me. Digital commerce is evolving quickly, and so are the risks that come with it. When I talk about our AI solutions like Adaptive Checkout or Dispute Resolve, I am not just focused on features - I'm focused on trust. At its core, our work is about strengthening the relationship between businesses and their customers. In an era where Agentic AI is about to shop on behalf of humans, the stakes for safety and accountability have never been higher. My responsibility is to ensure Riskified has the space and resources to innovate without losing sight of that trust.

The moments that once felt destabilizing - economic collapse, immigration, a rescinded job offer - weren't detours. They were stress tests. They trained me to stay calm when conditions change.

For women entering fintech today, my advice is to lean into the hurdles. Markets cool. Roles disappear. Plans unravel. A setback isn't a verdict, it's information. The question is what you do with it.

Technical skill matters. But leadership begins when you stop asking, "What's my role?" and start asking, "What does the business need?" It requires understanding how value is created, where risk accumulates, and which decisions strengthen the company over time. The strongest leaders I know combine analytical discipline with judgment. They don't just ask whether something works today - they ask whether it will still work tomorrow.

I certainly wouldn't be where I am without the mentors and allies who saw potential in me before I saw it in myself. But I've also learned that you have to be your own loudest advocate. Don't wait around for an opening. Ask for the opportunity, view your challenges as stepping stones, and build the network that will support your growth.

If I learned anything from those freezing days in Sofia, it's this: volatility is part of life. The goal isn't to avoid it. It's to build resilience - in yourself and in the organizations you help lead.