Young Corporate
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Young Corporate

PayPal’s Executive Team Shared Their Best Career Advice

Here’s what they had to say

Most who aspire to a career in business, aspire to one day be a CEO.

It’s the top job. The big decision-maker. The role that gets heaps of praise when the company does well. And barrels of blame when the company doesn’t. It’s an impossible job filled with impossible tradeoffs, and only a handful of leaders are able to find success at it.

Most fail.

So when a successful CEO opens up about their career path, and what helped them get to where they are, it’s worth paying attention to. Even if you don’t aspire to the top job anymore — it’s a brutal one, after all — you can still learn a lot from their path upwards.

This week, PayPal’s CEO did just that.

With his company’s summer internship class kicking off their first day, Dan Schulman gathered his top leaders (the heads of Finance, Legal, Growth, and Technology) to share their Words of Wisdom.

The resulting discussion is a gold mine of career advice.
Here are three highlights.

1. Life is about change and growth

It can be tempting to think life moves in a straight path. That you’ll figure out who you are and what you want to do early on. And then you’ll settle in for the rest of your days.

But as the PayPal leadership team points out, that’s rarely the case. Instead, according to Schulman, life has a habit of “throwing a lot of curve balls.” He shares a number of stories throughout the discussion that highlight just how indirect his path to CEO has been.

For example, Schulman talks about how he was rejected from every single college he applied to. Not something you’d expect to hear from a Fortune 500 CEO. Instead, he spent time working as a truck driver, which gave him the clarity he needed to move forward with his career.

The company’s CFO, John Rainey, echoes this sentiment when he says:

No one’s career trajectory is ever just “straight up and to the right.” You are likely going to experience failure along the way, so treat the challenges you face in your career like an exploration.

And explore you should.

Know that life will keep you on your toes. Your career will take twists and turns. The solution, then, is to stay agile. To learn and to grow along the way. To make the most of your opportunities.

Schulman uses the phrase “relentlessly optimistic,” which summarizes his approach to adversity. In the face of challenges, he sees the positive. He sees the growth potential and pushes forward with courage.

We should all strive to do the same.

2. Be self-aware

The thread of self-awareness runs all throughout the discussion. While it’s not a new concept — the Ancient Greeks coined the phrase “know thyself” back in the 10th Century — the team at PayPal has advice to share.

First, they focus on the need for feedback. Louise Pentland encourages young professionals to seek out mentors. In her words, a good mentor will help you by “providing honest, objective, and solutions-oriented feedback.”

Jonathan Auerbach agrees. He says you should go a step further. When you’re provided with feedback, ask follow-up questions to ensure you understand it. And ask for advice on how to take action.

Next, the team talks about identifying what drives you. What motivates you and gets you out of bed in the morning.

Sri Shivananda sees this most when professionals hit a difficult time in their careers. When you run into a career crisis, the resolution most often involves, “looking inside and growing as a person.” You need to know who you are and what you care about before you can fully buy into a company’s mission.

Lastly, Rainey shares insight into how he’s helping his two sons decide what they want to do career-wise.

Whenever they’re asked about their futures, the common question they get is, “What are you going to do?” But I always tell them that perhaps the more important question to ask yourself is “how” you are going to do it. Building your career is not just about meeting your business goals; it’s about treating others with respect and conducting yourself with integrity every day.

3. Support others

None of these leaders reached the top on their own. They all had help along the way. A company, after all, is made up of individuals working towards a shared goal. Often, they have to prop each other up.

And in many ways, the unselfish act of being a team player can have positive career results. Here’s how Auerbach puts it:

Ultimately, if your team is successful, that will reflect positively on you as well. How your team perceives you — whether you put the best interest of your team ahead of your own — will also play a role in your own growth and career success.

Rainey, on the other hand, talks about how damaging team interactions can be. Early in his career, Rainey was invited to a big client meeting. As he was sitting down, a senior leader in the room told the client, “He is just the scribe; he’s just here to take notes.”

This was a painful learning experience. And it highlighted for Rainey the importance of making sure each team member knows they belong.

Finally, Dan Schulman concludes the discussion by sharing the most moving story of the day. Early on in his career, his sister suddenly passed from a brain aneurysm. Schulman was devastated. He needed time to grieve and his work needed to take a back seat. He had to rely on his team.

His team rallied around him, demonstrating the power of helping others. “It was a humbling experience,” Schulman says.


As you move forward in your career, take these nuggets of wisdom from the PayPal leadership team with you.

  • Remember: the path to the top of any company is full of twists and turns. Leaders need to be agile along the way. They need to look for chances to learn and grow. They need to bring relentless optimism.
  • Embrace: feedback. Often, others see us more clearly than we can see ourselves. Rather than putting up defensive walls, view feedback as an opportunity to move forward. And don’t forget. Career struggles, as tough as they may be, can help us discover the “why” behind our work.
  • Support: others around you. No one gets to the top alone. Business is a team sport, which means you need to surround yourself with good people. This will help your career in the long run. And don’t forget to step in when someone else is struggling. You have no idea what it may mean to them.

I write this little newsletter called Young Corporate.

Each Friday, I compile the best work and career discussions from around the web, along with some of my own writing, and send it out. It’s free.

It’s designed for Millennials and Gen Z. Hungry young professionals who want to grow their careers. Professionals who want to learn and use their knowledge to make the world a better place.

If that’s you, subscribe here.



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Stephen Mostrom

Stephen Mostrom

L&D @ SVB | Helping Tech Talent Level-Up Their Skills | Product Manager | Professor | MBA | Featured in The Startup, PGSG, and Entrepreneur’s Handbook