As a part of our interview series called “Women Of The C-Suite” , we had the pleasure of interviewing Melissa Smith.
Melissa Smith is the CEO and Chair of WEX Inc., a leading global financial technology service provider. Melissa began working with WEX in 1997 in finance for the financial technology service provider. She worked her way through numerous roles, including CFO and president of the Americas, and now holds its most senior position. Melissa served as CFO during the company’s IPO in 2005 and has continued to spearhead WEX’s dramatic growth, both organically and through acquisitions.
Thank you so much for joining us in this interview series! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?
Thank you for having me. Well, I started my career at Ernst & Young LLP and joined WEX in 1997 around the time when the company first became profitable. From the beginning, I could tell that WEX was a place where the company’s growth created opportunity and it fueled my need to be constantly learning, and I’ve been here ever since. WEX is a special place, and that culture draws in amazing, passionate talent who are very connected to our customers and their needs. We’re not the type of organization that stands still, we’re constantly working toward greater innovation and moving the business forward, which is something that I love about my role and the culture at WEX.
By 2001, I was able to work my way up to CFO and in that capacity helped take WEX public in 2005. Helping to lead the company through such a major transition was an incredible opportunity, and since then we’ve managed to grow our business through expansion into new customer segments, while expanding outside of the United States. Today, WEX is a top global financial payments service provider for businesses of all sizes across a wide spectrum of sectors, including fleet, travel, corporate payments and health.
Can you share the most interesting story that happened to you since you began leading your company?
I actually became pregnant almost immediately after starting my role as WEX’s first ever female CEO. It was a unique experience to work through with my board how best to disclose my pregnancy, and to ensure we were complying with the Securities and Exchange Commission’s rules. This proved to be more difficult than I would have thought, as we were unable to find any previous examples and precedents of female CEOs who had become pregnant during their tenure at a public company. Surprisingly, this was not that long ago, in 2014.
So, I spent a lot of time in my early pregnancy with WEX’s board, our lawyers, our IR firm and our PR firm devising the best plan of action. Out of an abundance of caution, we decided to do an interview with The Wall Street Journal, in which I announced my pregnancy, which was a bit surreal — telling the world about something that is normally discussed in a more intimate and personal way.
Immediately after that interview was published, I received an influx of supportive communications in and outside of my company, including from customers and investors. Many of those notes talked about the importance of people being able to see women succeed in being both a mother and CEO, and not having to choose. It was incredible. By the time I had my twins a few years later in 2017, we were able to handle it with all of the knowledge we gained from our first time through. At WEX, we believe in picking multiple lanes in life, which means that people can live their whole lives and not have to pick a family vs. a career.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?
Our global headquarters are in Portland, Maine. In one of my first interviews many years ago when walking into the office, my heel got wedged into the cobblestones. Not only did the shoe drop off my foot, but became so ingrained into the stone that I had to drop onto my knees to dig it out as people walked by into the office. Life often doesn’t go as planned. I think it is important to keep a sense of humor and remember that you have an ability to impact others’ thoughts and feelings by how you react to the unexpected.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
From a young age, my mother pushed me and my two sisters to be independent. She wanted us to have the freedom of choice that came from having a career and an education. She encouraged us to push through the discomfort of trying new things, especially if they were hard. I grew up on a working potato farm in an incredibly small town in Maine, with only about 400 people. My parents were divorced by the time I was two, and my mother worked incredibly hard to support us as a single parent before she married my wonderful stepfather.
She really helped to prepare me for life, by not letting me take the easy way out, encouraging me to be willing to try new things, and modeling the importance of hard work. For example, when I was old enough to see over the steering wheel, I drove the hay truck, which was a great lesson in accountability because if you popped the clutch and knocked the hay off the truck, you had to get out and pick it up. She taught me that there were always going to be obstacles and for that, and many other things, I’m grateful.
In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?
This is such a timely topic. Every day in conversations I’m struck by how the pandemic has increased stress for most people. I believe that women shouldn’t have to pick between a career and a family, and I also know that the reality of doing both can be very hard on any given day. I think it is really important to find that stress release valve and to ensure that you have an ability to create and preserve your energy, so it is there when you need it.
For me, that is running. I have an intense need to spend time outdoors, even if that means I’m running in the wee early hours in the morning. I have a running partner so I’m accountable to someone else to show up and that makes it more likely that I will. However, if I am really sorting through something difficult, I will hit the pavement by myself and just let the thoughts roll. Time and distance fall away and I am able to think through multiple angles, which is really helpful going into something stressful or high stakes.
In addition, I will role play with someone that I respect. For example, if I am going into a complex negotiation, I’ve asked board members what they would do if they were on the other side of the negotiation so that I can play through the potential outcomes live. I find preparation in these settings is very important and external perspective is invaluable.
As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?
I have witnessed first-hand the benefits that a more diverse executive team brings to a business in both results and culture. At WEX, our culture focuses on allowing people to show up with their whole self. We call it “you be you” at WEX. You can see the benefit of this in our inclusion scores. At the same time, I also want to encourage creative conflict. We want our teammates and our leadership team to question one another when it’s appropriate and suggest alternatives as it often leads to better decisions. And this is best achieved with a diversity of experiences, backgrounds and thoughts.
When we hire new people at WEX, we really prioritize the unique experiences they can bring to the table. In fact, 40% of the executive leadership team is female and over one third were born outside of the United States. Having a more diverse leadership team isn’t just great for business though, it’s also good for internal culture. We want our executives to understand and address the needs and concerns of our people across the company. Going back to my own story, I think it was really encouraging for a lot of people to see a woman go through pregnancy and motherhood while leading a company. When you represent a minority, your physical presence becomes symbolic and more important than you might think, and it better humanizes the role of CEO. In fact, some of the issues I faced while pregnant and on maternity leave helped me to better understand the needs of working parents at WEX and we ended up adjusting our policies. That representation matters.
As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.
One key factor in building a more inclusive, representative and equitable society is trying to see things from another’s perspective. Leading authentically and with an understanding that the decisions I make as a leader will affect a lot of people helps me to make the most thoughtful choices I can. In employee roundtables, I really listen. I don’t have to agree with what each employee is saying, yet I can listen and consider different perspectives.
At WEX, like at many companies today, we have ERGs that connect people with shared interests, cultures, identities and backgrounds. Helping people with a shared experience come together and discuss the issues they face and possible solutions in a safe space allows for a greater sense of inclusion. ERGs bring people together as a group and can help people feel empowered to bring something up that they may have been intimidated to do so as an individual. It’s also important to be clear that there is enough success to go around for everyone.
Representation in leadership really matters. When people can see someone, who looks like them or has a similar lived experience to them in leadership, that can be motivating and also often helps to break down invisible barriers that may have existed in the past. Once it’s been done, it’s easier to do again. In terms of building a more equitable society, inclusion and representation are intricately intertwined. It’s essential that we recognize individuals for their own unique strengths and hard work to build a more diverse and equitable society. That also comes down to leadership recognizing that while we make the tough decisions, we couldn’t be as successful as we are without all of our people. We really aim to ensure our people feel supported and valued.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?
In my day-to-day, I do a lot of the things you would expect: provide strategic and operational leadership for WEX, focusing on not just what gets done, but how it gets done, because that impacts the culture of the company. I seek opportunities for expansion, ensure that the company maintains a high level of social responsibility wherever we do business which ties into our cultural values, assess the risks to the company and ensure they are monitored and minimized, advance and develop talent and communicate to all of our stakeholders. At the core of all of this, I build relationships with all of our constituents: our customers, our shareholders, our partners and our employees. Relationships live at the core of how work gets done and is an integral part of success.
Ultimately the major difference between my role and other leadership is that the final responsibility and ownership for the direction of the full business begins and ends with me.
What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?
I think one of the myths I would like to dispel is that CEOs are this hierarchical figure who omnipotently makes all decisions. I think it is dangerous to believe that any one person has all of the answers. Often, there is someone deep in the organization that has better specific content knowledge of the matter at hand and technical skills to make the call. I actually spend a lot of time listening to the perspective from different areas of the business and externally to make the most informed decision that will be beneficial to the whole of WEX, when a decision needs to come to me. Equally importantly, we have spent a great deal of time clarifying who owns decisions, to increase the pace of our movement and push decision-making to the appropriate place within the organization. While I owe the results of our collective choices, it’s really a team effort.
In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?
Well for one, the concept of pregnancy and motherhood. The anxiety that I felt at telling my board and disclosing my pregnancy at the beginning of my tenure as CEO is just not something that men have to face. I had to make a very vulnerable and private part of my life public, and I had to face the very real possibility that this extremely common and exciting time in my life could be detrimental to the business and my career. Luckily, it wasn’t, and we’ve only grown stronger ever since. But I think that initial anxiety is something that a lot of women in executive — and non-executive positions face.
We’re also often judged differently than our male counterparts. I attended an event once where they had researched the impact on being female on politicians. They found that if a female candidate’s hair wasn’t well done, it didn’t matter that she was saying the exact same thing as her male counterpart, people were less likely to hear what she was saying and retain it. The standards aren’t always the same.
What is the most striking difference between your actual job and how you thought the job would be?
One of the things I will always remember is walking down the hall at work the day after I had been named as the next CEO. It was the same hall, the same people, and I was the same person. Yet suddenly everyone treated me differently. They were more cautious. I had to separate myself from the role and realize that the role would create a perception that I have to be aware of. I work extra hard to try to be approachable to compensate. I think it plays into why people talk about the role of CEO as being lonely.
Do you think everyone is cut out to be an executive? In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?
While I think most people have the innate capability to be an executive, it’s not for everyone. You have to really love what you do and be comfortable with discomfort and trying new things. Each day I carry home the responsibility for our over 5000 employees, their families, our customers and our investors. Some days that can be a heavy load, other days it is a tailwind. Having interests outside of your career or multiple lanes in life are really important if you want to feed your soul in a way that creates energy, but it is challenging to carve out time for everything.
If I were to boil it down to a couple of traits, I would say that it is important to have fire in the belly or persistence. Success is often not a straight line and how you handle the bumps are very important to your ability to lead. Yet you also need to be able to get things done. It is important to be able to grow talent. As you progress in your career, it becomes less about you and more about the environment you create and the people you surround yourself with. And lastly, I think it’s important to be decisive. You will make a plan, execute on the plan, and the world around you is impacted, which can be an intimidating concept to handle.
If you don’t feel that being an executive would be fulfilling or you’re not in it to better the positions of all those around you, I think you should avoid the aspiration to be an executive. If it’s not going to bring you joy and you’re not in it for the right reasons, then it may just not be the right career path.
What advice would you give to other women leaders to help their team to thrive?
My advice to other women in leadership is to not only mentor the people on your team but sponsor them. Advocate for the success of the people you work with and help them learn and gain new experiences. Prioritizing the growth of your people and also leading with empathy is the best way to build a successful and thriving team.
And finally, there is inherently a negative voice that tends to run in many female leaders’ heads. One of the tricks to success is learning how to shut that negativity down. It’s important to acknowledge your feelings, build connections, challenge your doubts and avoid comparing yourself to others. If you have it running in the back of your head, it will distract you from achieving your goals and can eventually take a toll on your performance and emotional well-being.
How have you used your success to make the world a better place?
Growing up in a small, largely poor town in Maine, I learned the benefits of community early on. I wouldn’t be where I am today if it wasn’t for the lessons I learned from my mother and the opportunities and support I gained from my community. Now that I’m the CEO of a company based in Portland, Maine, I really like to use my platform to help foster growth in the community. Our employees give time to volunteer in the community, we donate money and we aim to create an environment where people don’t just care about one another, but we also care about making sure the place we live is thriving. Not only is this beneficial to the community in which we live, but it also drives a sense of purpose.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
It’s not so much a quote but a motto, which is “why not?” My mom instilled this in me early on. Whenever me or my siblings would talk about something we couldn’t do she would ask “why not?” I think a lot of things you think you can’t do are self-imposed, you put that burden on yourself, and my mom was there to push me and to encourage me that I could do the things I thought I couldn’t. Throughout my life whenever I found myself saying I couldn’t do something, I would stop and ask myself why I thought that. And that mindset has been instrumental to my success and where I am now.
We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them
I’m very enamored with women that use their success to help make the world a better place. Oprah Winfrey has created a career, and used her success to help many others.
