Whether you’ve risen to the top of your field in business or politics, sports, or the arts, there’s one question that you’ll inevitably face, regardless of the specifics of your profession: “How did you do it?”
There are many ways to answer this question, which is why it keeps getting asked, but the most engaging responses are often given by people who began their careers at the very bottom of their industry’s ranks, people whose first job was facing customers, or sweeping floors, or answering phones at a front desk. These professionals are often hardworking and talented, and they possess wisdom that is hard to gain just through reading about the industry: they have seen how the business functions while playing a broad variety of roles that enable that functioning.
Lynn Alexander’s story is woven from that cloth. She began her career as a summer temp in WEX’s warehouse and is now an executive for the company overseeing multiple departments at WEX, with myriad responsibilities and teams reporting up to her.
How Alexander Started to Earn Her Chops
Alexander is based in our South Portland, Maine office and just celebrated her 26th year with WEX in March of 2020. When talking to Alexander, you get a sense of why she has stayed at WEX for so long, “I am at my personal best in a fast-paced environment with rapid change and WEX has been just that for most of my 26 years here. There is always an opportunity to be challenged, to do something different, or test out different ways of running operations here.” She is responsible for non-contact center operations for WEX’s North American Fleet and OTR lines of business. This includes partner, merchant and network operations, indirect tax, disputes, check administration, controls and compliance, card production, and logistics.
New England Roots Run Deep
Alexander grew up in Westwood, Massachusetts, and went to high school in New Hampshire. Growing up in New England, she came to Maine on vacations as a kid. Her family made the trek north to visit relatives from her dad’s side of the family, the Greely family out of Cumberland. Back then, Alexander wasn’t looking at the state as a place where she would make a home for herself.
After over 40 years away from the place where he grew up, Alexander’s dad moved back to Maine the year Alexander graduated from college. She decided to spend her first summer post-grad visiting with him and made the trip up to Maine from New York, where she’d gone to college. She saw herself swinging in for a quick visit and then heading off on other adventures and had no intention of staying beyond the summer. But, as happens for many who cross the bridge from New Hampshire, by the end of the summer Alexander had fallen in love with Maine, the state of her ancestors. She decided to stay.
Alexander landed a temporary job with WEX that summer working at one of our distribution centers responsible for mailing out customer invoices. Once she decided she was going to stay in Maine, Alexander did something not every young twenty-something does: she took stock of her options and put some thought into how she was going to advance her career within the organization. Amidst that thoughtful and forward-thinking time, Alexander was hired to a permanent, full-time position at WEX. In the distribution center where she’d started as a temp, she had been promoted to team leader.
Learning the Business of WEX One Job at a Time
While working as a lead in the distribution center, Alexander began to understand WEX’s business and it was then that she decided she wanted to move from the warehouse to the contact center. As she describes it, she wanted “to get the greatest exposure to our product set and our customer base.” Alexander spent ten months in the contact center. “Working in the Contact Center afforded me a better base of understanding of our products, our customers, and our operations as a whole. The time I spent as an agent on the floor was invaluable and it allowed me to develop a more comprehensive understanding of WEX.”
While in the role of team lead, Alexander was given the opportunity to start a fraud program for WEX. “This was back in 1997 and at the time WEX did not have a fraud department but we started to see pockets of fraud-type behavior on the cards. A fraud analyst position soon opened up and I spent the next 10-12 years building out the fraud department.” Alexander studied sociology and criminal justice in school which contributed to her interest in the role.
Alexander knew she couldn’t build out the fraud department with what she knew in her own head alone. She needed to tap into a wide variety of resources. She joined the Association of Certified Fraud Investigators and the International Organization of Financial Crimes Investigators which provided her with an open line of communication with other professionals in her field. As she built up her team, she pulled people from outside the organization with experience in fraud analysis to help round out the knowledge base within her group.
Though she pulled new people into the fold from outside of WEX to build her fraud team, Alexander always preferred to seek talent from within first. As she explains it, “Sheer grit goes a long way.” She believed in hiring people whose determination and stamina set them apart: “Look for those good strong workers and teach them what they need to know to be successful on your team. As a candidate, you don’t necessarily need to possess a certain skill set, especially considering the nuanced skillset a fraud role demands. If you have the ‘fire in the belly,’ or the grit or the determination to learn something, those ancillary skills to do the job can be taught and learned.” Alexander hired people that had the knowledge and a background in fraud analysis, but she was also interested in training people so she could develop talent from within the ranks of WEX.
Ready for New Challenges
Having accomplished building a strong fraud department for WEX, Alexander felt ready to take on a new challenge. At the time, WEX was launching a new product set referred to as “Distributor.” She describes Distributor this way: “We had all the major oils at the time and we offered card programs for them, but we were going for the next layer down in the regional distributors that wanted to offer their own branded card programs. We were launching that product and WEX was looking for someone to manage that department, that operation, and that product launch so I took that on.” Alexander’s role evolved over the next several years into her current job, by combining departments and adding different functional areas. She managed “Distributor” and then managed “Partner and Merchant Operations.” From there, Alexander became a Director and then eventually a VP, the role she currently holds. “I got to the position that I’m in now through merging and consolidating different functional areas and really building out a client service operations group. The group that I now have encompasses partner operations for North American Fleet and the OTR lines of business and I manage the partner operations, the merchant operations, card production, logistics, tax exemption for the fleet customers. I have a number of different responsibilities that are all related to the non-contact center operations, essentially. Everything comes full circle because about 18 months ago I actually took on the distribution center. Where I started is now back with me.”
How Empathy Plays a Role in Leadership
Alexander’s history with the company has given her a true sense of the daily experience of a lot of different jobs at WEX. As she puts it, “You have a certain amount of empathy for people in all levels of our company because you’ve been there. I’ve walked the walk in many of the different positions – everything from collecting from our customers, being on the front lines answering their calls and dealing with them when they’ve had a fraud event. This could be a situation where they’ve been taken advantage of by someone, whether it’s one of their employees or some third party. So, I’ve had a lot of those direct experiences.”
This empathy contributes to Alexander’s passion for developing the people on her team, keeping them challenged, supporting them in meeting their ambitions, and developing their careers. She has people working for her who started in entry-level positions and are now in management roles. And she’s had folks who’ve been in leadership positions under her who’ve been able to move and leverage those skills in other areas in the company.
Some of Alexander’s compassion and abilities as a teacher and leader may come from her mom. Alexander explains, “My mom has had the most powerful influence on my life. She was an incredibly strong woman who fluidly balanced parenting with being a career woman in the late ’70s and ‘80s when that was not commonplace. Unfortunately, she succumbed to a battle with cancer much too young. It was her inspiration that compelled me to participate in my first triathlon, one of the early Tri for a Cure events, serendipitously sponsored by WEX.”
Guts to Do a Tri, Guts to Take Career Risks
Alexander took part in one of the earliest years of the Tri with a group of WEX women. She participated as an individual, which meant she was responsible for completing all three legs of the race. About the Tri, Alexander says it was “Inspiring and emotional at the same time. I don’t think there’s anything like it. At least in the state of Maine. It was an incredibly moving experience, for many reasons.”
Committing to a triathlon takes guts. It’s clear from talking to Alexander that she doesn’t allow fear to stop her from attaining her goals. “Some of the absolute best things I’ve ever done, the ones with the biggest payoff, have resulted from the scariest decisions I’ve had to make. If I could, I would tell my 18-year-old self to take smart risks and try the things you’re most afraid of doing.” She goes on to describe a risk she took at WEX that she feels was pivotal to her growth as an employee: “One of the most memorable decisions I had to make was related to the story I told earlier about how I spent 10-12 years building out the fraud department. That was my comfort zone. I knew the position inside and out. I knew the function inside and out. But I was looking for something more. So, my head was telling me to figure out how to continue to grow my career. Everybody gets comfortable in their zone so when I was offered the opportunity to make that leap into something completely different it was incredibly scary at the time. Everything in me was holding me back and saying no, stay with what you know and what you know you’re good at and that imposter syndrome really set in where there was some fear that I would not be successful but I pushed through it, made the leap and I’m so glad I did.”
Alexander’s wisdom and work ethic, her focus on training and sharing knowledge, make her an exceptionally valuable member of WEX’s team. We’re so glad she made that decision 26 years ago to put down roots here in Maine, and create a career for herself here with us at WEX.