UPFRONT & PERSONAL: A Conversation with Louise Pentland, Chief Business Affairs & Legal Officer at PayPal

Topics: Corporate Legal, Efficiency, Leadership, Legal Innovation, Talent Development, Upfront & Personal, Women’s Leadership Blog Posts

Upfront & Personal

Today we continue our new feature on the Legal Executive Institute blog, “Upfront & Personal.” The column, created by Rose Ors, brings “the person behind the title” to the forefront in interviews with of some the most influential members of the legal community.

Louise Pentland, Executive Vice President, Chief Business Affairs and Legal Officer at PayPal, spoke recently with Rose Ors, the CEO and Founder of ClientSmart, about moments that have defined her, the power of knowing yourself, and how motherhood changed her management style.

Rose Ors: What life moments have defined you?

Louise Pentland: There have been a few events that have defined me. The three that have been especially profound are leaving home when I was 18, having my daughter at 40 and the death of a work colleague.

Rose Ors: Let’s begin at the beginning. How did leaving home define you?

Louise Pentland: When I left home at 18 I was completely independent. I rented an apartment on my own and, for a year, worked three jobs to pay the rent and my other bills. It was very grounding to be fiscally responsible so young, to understand what it takes to pay the bills and how hard it is to work for minimum wage. I knew I wanted more and I applied to university and began my law studies at 19. In England, the study of law is part of a six-year undergraduate and graduate program. I also paid my own way at school. So, I worked harder, valued my education more, and thought more about what I was going to do with that education, because I was paying for it.

Rose Ors: How did becoming a mother define you?

Louise Pentland: The birth of my daughter forced me to get much better at managing my time. I made sure that the time I was at work was concentrated and intense, so I could be free to be at home with this wonderful joy that had just appeared in my life.

Rose Ors: What was the most difficult aspect of going back to work?

Louise Pentland: Having to trust other people to look after my baby. When I had my child, the company I worked for was in a bit of a crisis. So, I went back to work full time after only two months. I didn’t have the luxury of a typical European maternity leave. I still remember how very hard it was going back to work.

Rose Ors: In what way has being a mother influenced your management style?

Louise Pentland: I’ve always been a great advocate for women, but I think it’s hard to truly empathize with the struggle of being a working mother until you are one. Similarly, I’d always intellectually understood the need for parents to attend their children’s after-school events. But until I had my daughter I did not know the emotional importance of those events. Having a child has not only changed how I manage my life but also how I think about how I manage my team. I’ve become a much more empathetic and accommodating manager. I understand you don’t get lost moments back. You need to treasure them when they come along.

Rose Ors: Is there an experience that has influenced how you approach your work?

Louise Pentland: In 2007, I was heading up the legal team of one of Nokia’s business units. Up to that point each business unit at Nokia had its own legal team and the team reported to the business unit. In response to corporate disasters like Enron and the passage of Sarbanes-Oxley, the company hired its first general counsel. Eighteen months after joining us, he passed away.

For me, the experience had an immediate and lasting impact. I remember saying to myself at the time that — although I’m a self-professed workaholic — no matter how much I love my job, I never want to die there. I remember that being a profound moment for me.

Louise Pentland, Executive Vice President, Chief Business Affairs and Legal Officer at PayPal

Rose Ors: How has that “aha!” moment influenced your approach to your work?

Louise Pentland: A demanding job requires a demanding schedule. That’s just the nature of it.

What happened at Nokia did not change my commitment to my job. But what it did do was make me think differently about how I spend my time at work. If I’m going to come to work and spend 15 hours away from family and friends, the work I do needs to count — it must have purpose. It’s why I joined PayPal.

The experience also made me realize that life is more than just work. I can’t just be a self-confessed workaholic, I need to be a great parent, a great spouse.

Rose Ors: This is a nice transition to the next question. What career advice would you give your 20-year-old self today?

Louise Pentland: Learn what makes you tick. Learn what you’re passionate about. I wish I had understood the power of knowing yourself when I was a law student. We get so confused with, “Well, I need to go to the best Ivy League school. I need to get to the best law firm.” Frankly, those things don’t matter as much when it’s all said and done. When it comes to that day of reckoning, whatever that is, and you look back and you say, “What did I do that made a difference?” That’s what I think we should be asking ourselves. Then asking, “How do I get there?”

Rose Ors: How do you learn what makes you tick? Or what you’re passionate about?

Louise Pentland: Part of it is your moral compass and that’s something that I think you develop with time. But you need to ask the questions. And, it may be that, what makes you tick is working for the best law firm. Great! You just need to be intellectually honest with yourself. I think if I had asked those questions I may have taken different steps than those I took. I might have done other things along the way.

Rose Ors: What’s an example of another path you might have taken?

Louise Pentland: I look at people today who, for example, are working at non-profits. I’m on the board of the Law Foundation of Silicon Valley, and the lawyers there show up every day and they love what they do. They want to have what they do matter — and it does. Their work has a profound, dramatic impact on people’s lives.

I don’t regret anything. I just would have liked to have known myself better earlier in my career journey. I’m happy where I am. I would just say that I got here somewhat by accident and somewhat by design. I think it’s only when you understand what motivates you and understand what matters to you, that you can be more selective about where you direct your career.

Rose Ors: What was something you did by design?

Louise Pentland: My decision to join PayPal was definitely by design.

I intentionally took 10 months off work while conducting my job search. During that time, I defined the three things that I was looking for in a company. These were non-negotiable requirements. First, the company had to have a moral purpose that advanced society. I needed to be able to go home at night and look my daughter in the eye and say, “Here’s why mommy goes to work. It’s because I want to make this a slightly better place for you when you grow up.” Secondly, the company’s culture and values had to mean something. They had to be more than slogans on posters that people memorized. They needed to be translated into action. Lastly, it had to be a growth company.

Rose Ors: And PayPal met all three criteria?

Louise Pentland: Yes. At PayPal, I feel part of something that matters and that can make a difference.

Rose Ors: What inspires you, Louise?

Louise Pentland: People who try new things inspire me. Innovation only happens when people try something new. I thrive in an atmosphere, at work and at home, where trying new things is encouraged and failure has no shame. I don’t like to play it safe.

Rose Ors: If you could only keep five possessions, what would they be?

Louise Pentland: My glasses since I’m losing my sight as I get older. Also, a ring that I bought when my daughter was born. I don’t come from a family of heirlooms but this ring I treasure. Other possessions I need are my cell phone and my kettle and teabags.

Rose Ors: What advice would you give a newly appointed Chief Legal Counsel?

Louise Pentland: My advice is to surround yourself with really talented people and then listen to them. And learn the business.


The interview has been edited and condensed by Rose Ors.