Louise Pentland: EVP, Chief Business Affairs & Legal Officer at PayPal

Louise grew up in a very working-class family in the north of England, and her father was a self-employed coal merchant. He lost his business and tried to reinvent himself, but he didn’t have any education to fall back on. Early on, Louise learned about the importance of optionality. Being exposed to her father’s situation at a very young age drove her towards a career that required a strong education and provided significant stability.

When she was sixteen, she was able to intern at a law firm. Additionally, Louise always chose the lawyer track when playing family board games since a doctor or lawyer would make more money than other professionals in games such as Life. She wanted to work in business, and she was fortunate to have a mentor in high school who advised her to pursue a law degree since one can always work in business with it. Her mentor said that one can do anything with a law degree, so she did that, and it paid off. Louise was always inclined to be in business, so she chose not to follow a law firm path. This choice allowed her to have the best of both worlds since she has a law degree and considers herself a business leader.

Louise was the was the first person in her family to go to college and she was not encouraged to do that. Those external influences really shaped where her career went and who she is as a person. 

Who do you look up to?

Throughout different phases in my life, there have been several different influences. My business and law teacher had a big influence on me. He got me to think pragmatically about where I want to go to college since I didn't have anyone in my family who had been to college. I would have loved to have participated in the programs that exist for high school girls interested in technology today. I would have loved to have something like that, and I wonder how much stronger I would have been today if I had gotten those opportunities in my formative years. Once I got into business and I went through some painful years in the law firm where it was predominately white males, I realized that was not the world I wanted to live in. So, I moved across the country to work at Avon Cosmetics, which was a company about women by women. Once I was there, I embedded myself with the marketing team because I loved what they were trying to do. I was so used to being in male-dominated spaces and that drove me to work for a company that cared about helping women. 

Then, I got headhunted by Nokia, and I went to the company in 1988 thinking I would be there for 2 years but ended up staying for almost 17 years. I worked in an incredible culture. I had amazing legal leaders, and my first boss there was so humble and never made me feel bad about not knowing everything. I learned so much from her and many other leaders there encouraged me to be the best I could be. I was promoted before I was ready, and I got the opportunity to work for Mary McDowell, who was the head of the enterprise business. I did not know enough to be in that role, but she trained me, coached me, advocated for me. I worked very hard, and I felt very grateful for the opportunity to be Chief Legal Officer when ours had unexpectedly passed away. She was my biggest advocate with regard to me becoming the acting Chief Legal officer. I was 36 years old, and that usually doesn't happen. Then, 10 months later, I was permanently appointed to the role. It happened because I had these incredible male and female mentors and because I was in an environment that was very nurturing and made me want to be the best version of myself, I continued to evolve and became very established in my role. When I made the decision to leave after we sold a big part of our company to Microsoft, one of my mentors became the chairman of the board. The chairman of the board told me to find a company where the mission is strong and look for a culture I could help shape, which is what led me to PayPal. 

I became a mother very late in my life, I was 39 and I was in the C-suite heavily pregnant. Another one of my mentors was the former Chief Marketing Officer of PayPal who has been a working mother her whole career, and she is absolutely amazing. I held onto her as a professional mentor. I have built this amazing network of amazing role models who I leverage to mentor me and I try to give back to them. My mentors and role models have evolved as my life evolved. I have been able to be an advocate for other women and help them understand that they can become a mother while in a C-Suite position. Now at PayPal, I have a CEO who has changed the world, and he is the most humble person with the biggest heart. I do not think my path would have led me to him if I had not have had all of these experiences and mentors. 

What is the greatest risk you have ever taken?

I have taken a lot of risks outside of work. I have jumped out of planes. I have also taken a lot of risks on people that have mostly paid off. Sometimes, they do not. 9 times out of 10, risks do pay off. I took a risk coming to PayPal since I didn't have a financial services background, and that really challenged me to learn something new. I could have easily stayed in my comfort zone and worked at a company closer to what I had done before, but I wanted to see if I could be successful in a very different environment compared to what I had been used to. I also took a year off before I came to PayPal, and I decided to help with the immigration crisis where kids were coming from South America to Texas since I was living in Texas at the time. I decided to go volunteer and represent these children in court because they were frequently being sent through the court system with no language skills and no legal representation. I did not know anything about immigration and I partnered with a human rights group who mentored me. The next thing I knew, I was standing in the federal immigration court representing these children. It was one of the scariest moments of my career because I realized if I messed up, these children would be sent back and potentially that could be a death sentence. I remember thinking to myself, Louise you can't mess this up. 

When was a time you wanted to give up, and what made you persevere through it?

When I was appointed as the acting Chief Legal Officer at my previous company, it was a challenging situation where the previous officer had died in a very tragic accident. I had taken a very short vacation, and I received the call saying my boss had died and that I would become the new acting Legal Officer. At that moment, I wondered why I had been selected for the role. There was a strong reaction from people who had been my peers and good friends who were upset they had not been chosen. At the time, I was unsure whether that job was really worth it. I had spent decades building up these relationships and they were creating a lot of noise and bad feelings. The team was fractured and it was hard for me to become an inspirational leader for them. I brought in a consultant to help the team heal and the team became so much stronger and unified after that. I really tried to be a facilitator and as I started to do that, I realized their frustration laid in the lack of information about the decision and less about me as a person. It was an interesting moment because I was still recruiting people for the permanent position for the Chief Legal Officer and I remember calling Brad Smith, who is the Chief Legal Officer at Microsoft. I asked him if he knew someone for the role as he had a great network and he said that he thought I would be a good fit for the role! I look back at that moment, and I realize that my leadership skills had already evolved significantly. There were times when I questioned if it was worth it but I persevered, and I now see that it changed everything about how I am as a leader.  

If you did not have to worry about money, how would you choose to spend your life? 

Since I became a mother, I have already started to do some of this. I would love to spend my time doing something for missing children and exploited women and children. I think about that a lot and about the anxiety and stress that the situation creates on everybody. I would like to do something in that arena. 

What advice would you give your younger self? 

I would say do something that you are passionate about in life that you can have fun doing as well! It is always possible to evolve and change the current situation. There is no age limit on the possibilities and opportunities that are available to you. 

What is one dream you have yet to accomplish? 

One of my big goals is to chip away at the need for Silicon Valley to be more diverse and an equal level playing field. I wanted to make a dent in the lack of representation in the Valley and in the field within which I operate. I am a minority as a Legal Officer in a Fortune 200 company. The number of women in the role is below 20%, which makes absolutely no sense to me. It should be closer to the 50% range. I still have a lot to contribute to before I think my work is done. 

If you could change one thing about the world, what would it be? 

Right now, it would be the lack of tolerance. I think if people were more tolerant of one another and took the time to understand one another, the world would be a kinder place to live in. We have taken a lot of steps back in the last 6-7 years. If we could accept that everyone is different, it would be a large step forward.