The CEO who made PayPal a household name

Dan Schulman has led some of the most iconic companies in consumer finance, telecommunication, and e-commerce, including PayPal (PYPL), AT&T (T), Virgin Mobile, Priceline, and American Express (AXP), with game-changing innovation and bold risk taking. In this episode of Yahoo Finance’s Lead This Way, the former PayPal CEO and President shares the values that have driven his decision making as CEO of several of the world’s most iconic businesses.

Recognizing that employees are essential to a company’s success, Schulman put in place an extensive program at PayPal that prioritized their financial wellness. Mentored through a tradition that business can be a force for good in society, Schulman has taken principled stands on critical social issues and has led with purpose, compassion and authenticity, while more than tripling the annual revenue of PayPal during his nine years as CEO.

The outgoing PayPal CEO and President sat down with Yahoo Finance Executive Editor Brian Sozzi at PayPal headquarters in New York City to share his vision for what makes a good leader. Central to his approach are an adherence to four key attributes: being humble, generous, authentic, and bold. Schulman sums it up by saying, “You have to have the confidence to make difficult decisions.”

Schulman’s storied history as an executive began in the late 1990s as President of AT&T’s Consumer Division, which subsequently led to CEO positions at Priceline and Virgin Mobile. He was President of Enterprise Growth at American Express before taking the helm at PayPal, from which he resigned in September of 2023.

Lead This Way is a new series that features big interviews with the business leaders shaping our world today. In these one-on-one conversations, we reveal how their approach to leadership helped them become Wall Street titans.

For more on our Lead This Way Series, click here, and tune in to Yahoo Finance every Thursday at 3 p.m. ET.

Video Transcript


DAN SCHULMAN: To me, profit and purpose go hand in hand. Business can be and should be a force for good. But you have to have the confidence to make difficult decisions.


Dan Schulman is on the Mount Rushmore of CEOs from the past two decades. He was brought on as CEO of digital payments powerhouse PayPal in 2014 to guide the company through the split with eBay.

In his nine years as PayPal CEO, he’s taken bold stances on contentious issues and prioritized the financial health of his employees. At his core, the now former PayPal CEO leads with purpose, compassion, and a vision of business being a force for good.

BRIAN SOZZI: I was thinking back on your leadership through the years of PayPal. And one thing among many certainly stood out to me. Profits and purpose are not at odds with one another. And to me, that is how you led this company. Is that right? Why has that been so important to you?

DAN SCHULMAN: As the CEO of a large company, you have multiple constituencies that you’re trying to serve. Shareholders are, you know, one of those. But you need to focus on your employees. That’s always been kind of the centerpiece of what I’ve tried to do as a leader.

And so my view is if you wanna attract the very best employees– and the very best employees are the bedrock of any company’s success– you have to stand for something. And to me, profit and purpose go hand in hand. If you have a mission, a sense of values, motivated and passionate employees, you’ll do better over the long run than your competitors who don’t have something like that.

BRIAN SOZZI: And you gave them stock.

DAN SCHULMAN: I gave every employee stock in the company so that they would be owners. We raised wages. We wrapped it all in an educational, financial literacy program because I did feel like financial health is sort of the bedrock of my responsibility to my employees.

Over the course of his long career, Schulman has taken some of the most iconic businesses in consumer finance, telecommunications, and e-commerce to new heights of growth and prosperity. But there have been some serious challenges along the way.

BRIAN SOZZI: Has it been hard as a leader to take stands on key issues? And then how do you implement those key stands?

DAN SCHULMAN: Well, it’s always hard to take stands on issues. My view is you need to make sense because if values are just words on a wall, then they’re just propaganda. They’re not really what you stand for.

I think, you know, one of the first moments where I realized that is when North Carolina passed House Bill number 2, which in my reading of the bill allowed for the discrimination against somebody for their sexual orientation or their sexual identity. And I felt like that was anathema to our values. And so we pulled out of North Carolina.

I had no idea that it would be front page news of “The New York Times.” I had no idea the number of deaths threats that I would get as a result of that. But it’s those kinds of stands that are very difficult. But our customers expect that from a responsible corporate citizen.

BRIAN SOZZI: In that moment, what did you learn about yourself as a leader?

DAN SCHULMAN: I go by several attributes that I try and follow for leadership, like one is be humble. Admit to yourself you don’t know everything and that you’re constantly learning and listening. And either you say you’re humble or life will force you to say you’re humble. One way or the other, you need to be humble.

Number two is to be generous, to always think the best of people, to always feel like people have best intent possible. And then I think, you know, being authentic is crucial. And that’s kind of what I learned in these things, just like be yourself. Work on your own set of values and what you are and who you are.

And finally, you need to be both. You need to be quietly confident. You have to have the confidence to make difficult decisions, knowing some of them will be wrong and some of them will be very right. And that is what moves the company forward.

BRIAN SOZZI: So Dan Schulman the leader walking in the first day as CEO PayPal nine years ago to today, how are you different as a leader?

DAN SCHULMAN: Well, I think I’ve grown a lot. I’ve seen people who had left PayPal for dead, that we were gonna be a dinosaur. I think we are clearly a global payments powerhouse right now.

You know, I’ve probably become more values driven than ever before because I think in this world, you need to have a moral compass that drives your values. You need to feel comfortable with yourself, whether times are going great or not great, because you need to be a very consistent leader.

BRIAN SOZZI: How do you think PayPal employees will remember you?

DAN SCHULMAN: Well, I think they will think of me as a colleague who really cared about them, that tried to take care of them, making sure that they had financial health, that they could dream again about a better life for their kids, and that we were a role model corporate citizen, and that they could be proud of the company that we became. And I think the next chapter for PayPal will be even more exciting than the last decade.