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Women in Technology: WEX's Heather Andrews

Women in Tech: WEX’s Heather Andrews

November 3, 2021

In the middle of the last century, before “Women in STEM” was ever coined as an initiative to include women in the lucrative and intellectually rigorous fields of science, math, technology, and engineering, women were at the forefront of the technological revolution in computing. At the time, women like Grace Hopper and Margaret Hamilton were pioneers in engineering before computer engineering was a field of study or a career. Hopper, a Navy admiral, was a programmer who developed the ability to model the impact of atomic bombs. And Hamilton, an early coder, led the team charting Apollo 11’s path to the moon. Hopper and Hamilton were two examples of a larger story in an era where women made up over 50% of the team of programmers tasked with developing the US military’s first computer.

Women continue to make gains in their careers but are still lagging behind in STEM fields
Women continue to make gains in their careers but are still lagging behind in STEM fields

By the late 1960s, as the industry became more central to economic and business capacities which were historically dominated by men, the propensity for males to step into innovation, development and leadership roles quickly outpaced that of women.

In recent decades, women have made inroads back into this field. However, while women make up 52% of workers with a college education, only 29% of the technology workforce is made up of female workers. The percentage is creeping upward from 25.9% in 2018 and 26.2% in 2019, but there is still a long way to go for women to have significant involvement and influence in the STEM-led industries.

Heather Andrews, Vice President and GM of the Americas for WEX, has spent a long career in technology as the field has evolved, both for women and as the internet changed the way we live. Disarmingly warm, open and kind, Andrews is the kind of person you want on your team, in your pack, in your book club. Like many of the women in leadership at WEX, Andrews has remained true to her values and her singular focus of doing good while growing her career.

Childhood interest in STEM can be brought to bear in tech career

Andrews had a proclivity for science and math from an early age. “As I look back I think I was always naturally drawn to the ‘how’ of things, and math came naturally. When I was a kid we did ‘Odyssey of the Mind’ which is a competition where a small group of students team up to create a themed presentation and also do problem-solving challenges like building free-standing structures that interact to solve a problem. I loved the whole thing as it was artistic, creative and challenging.”

She remembers an Odyssey of the Mind project where her team had to study and present four aspects of culture. They devised and constructed a self-propelled vehicle, designed costumes, wrote music and a script, and developed replicas of architectural landmarks. The group automatically aligned with certain parts of the project with the assumption that the boys would tackle making the car, however Andrews was drawn to the science and creativity required to produce a motorized vehicle. Though it wasn’t the expectation, she joined the boys in their design and build work. Andrews followed her instincts without fear of what others might think. “What I loved about these types of projects, and what I continue to bring to my work is taking the technical and creative and combining them. That’s when it gets really interesting.” For Andrews to pursue what she loved and felt passionate about as a kid she had to ignore an impulse to conform to constructed assumptions about gender, and instead follow her interest, a decision that requires some pluck.

The math and science of music composition

Martin Bergee co-authored a study at the University of Kansas, published in the Journal of Research in Music Education, examining a correlation between learning music and achieving higher scores on math exams. After studying more than a thousand middle school students over the course of ten years, his hypothesis that there was no correlation was proven wrong. The study instead demonstrated that the more you study music, the better you’re going to be at math.

Music has been important to Andrews since childhood. In high school, she performed as well as composed and recorded music using MIDI, at the time a newly developed, state-of-the-art music arrangement programming tool. She is still involved in artistic and musical endeavors, participating in community theatre (she’s just finished playing a lead role in The Wizard of Oz, in which she participated with two of her children) and performing as a vocalist for local musical groups.

Because Andrews learned music in the Suzuki method, taught by ear as opposed to reading sheet music, her approach to composing is unconventional. She recently discovered this while developing vocal harmonies with her peers. While her friends were documenting their compositions with letter notes or marks on sheet music, Andrews was using numbers to map out her composition. Music for Andrews is about numbers and the relationship between notes. It’s more comfortable for her to think of composition and arranging in numeric terms. Andrews’s relationship to music has informed her interest in math and technology, though she loves both elements of her life for their own specific pleasures.

Adapting to social pressures sometimes comes with a cost, but can also lead to more worthwhile practices

Andrews was the kid we can all either remember or relate to who in elementary school sat at the front of the class and was always raising her hand to answer the teacher’s questions. “I had an answer for every single question and I loved talking to the teachers because I thought they were fun to talk to — they were intelligent and interesting.” But Andrews soon grew self-conscious and worried she was being misconstrued as a know-it-all. She started adapting her behavior and tried to suppress her eagerness while also realizing it was important to be her authentic self. “I didn’t want to lose myself. I knew well enough that I shouldn’t be ashamed of being smart but I also knew that if I wanted to have friends, if I wanted people to want me around, I had to rein it in – to not speak up sometimes.”

By recognizing the potentially unkind judgments of her peers, and adjusting her own behavior to adapt to social expectations, Andrews was protecting herself from a social environment that often rewarded males’ display of initiative while resenting the outward presentation of intellectual prowess of women and girls.

Andrews adapted by contributing to and celebrating the ideas of her peers – a skill she developed and honed throughout her youth and into adulthood that was, unbeknownst to her, a foundational leadership skill. She had to work hard in later years to find a balance between contributing a healthy amount and developing her ideas through collaboration with her peers.

Andrews’s solution – choosing to strengthen the group through collaboration instead of working in isolation to compete against her peers – was in many ways wiser, more compassionate, and more generative than whatever she might have accomplished by more consistently working solo on personal achievement. To this day, Andrews employs her natural ability to shine a light on others and away from herself when she promotes the ideas that her team has worked to develop. “I love highlighting the achievements of my employees and my teammates. I feel like it empowers and encourages them, and that is immensely rewarding to me.”

Role models for women in technology from a cross-section of heroes

When asked, Andrews doesn’t point to a singular role model in her life who influenced her career in technology. Instead, she speaks of a variety of female influences that have guided her. “I’m inspired by certain aspects of different people, and a lot of them have certain things in common, like Angela Merkel, Condoleezza Rice, Maya Angelou, Ruth Bader Ginsburg. These are inspirational people, there’s nothing secret about that.” From these icons of influence, Andrews finds inspiring “that confidence without being overbearing, practicing empathy while still being strong – it’s people who can balance the two major strengths, being compassionate and open while also being super confident and determined.” There’s a common ability held by these iconic figures of successfully embracing seemingly contradictory traits. They’ve crafted ways to retain the strengths associated with femininity  while embracing habits and customs that are less frequently connected to women, but that allow them to ascend in their careers.

Andrews also points to a childhood influence: one of her best friends’ mothers, a flight attendant who used to share stories of her global travels. Andrews came to realize that this woman’s job was a means to an end. Her dream wasn’t to pour coffee for business travelers on airplanes; her dream was to explore and learn from every corner of the world. She’d followed a traditionally feminine career path as a way into accessing experiences that women were often kept from through the tethers of motherhood and spousal obligation.

The valuable lesson Andrews gleaned was that there’s more than one way to get what you want out of life. She came to feel that being creative about how to find fulfillment would help ensure accomplishment and success. “She did that work to gain access to things that were impactful in her life. She got to travel, and when she did she engaged with people in different parts of the world which gave her global connections. She was intuitive, intellectual and open-minded and part of how she got her wisdom was pursuing that global view. Every time I struggle with ‘Am I doing meaningful work?’ I think of her.”

Bringing good to the technology boardroom

Andrews’ work involves inspiring people to be their best selves and she finds meaning in the small ways she can make the world just a little bit better for everyone who crosses her path. “Even when negotiating deals, I think, ‘I’m going to do something that makes everyone at this table feel like they just did something well.’ It’s allowed me to find a lot of joy and passion in what I do even if it’s not directly changing the world in some dramatic way.” Even when she’s sitting at the deal-closing table with all the interested parties, she is making a difference. “My biggest hope is that they walk away from that table to the next table and think, ‘This is a good way to do this.’” She’s keenly interested in the ripple effect she can produce through small acts of integrity and openness. How to work well with people, how to be respectful and inspire others, these are the recurring concerns that animate Andrews’s relationship to her work.

Networking is the cornerstone to developing impactful business relationships

Andrews joined WEX in 2014 with the acquisition of Evolution1, a health fintech company she brought to the market with a team of ambitious entrepreneurial professionals. This acquisition formed the foundation for what would become WEX’s health division. While Andrews enjoyed the opportunity to work with WEX to fold Evolution1’s products into WEX’s, she knew that she wouldn’t remain in WEX’s health department forever. By the time she’d developed a strong, independent team to take the reins of her department, Andrews was ready to do something different. She started to explore what other opportunities might exist at WEX. She was still learning about WEX’s culture and determining if it was a company she wanted to commit to for a longer period of time.

One way Andrews explored WEX was by contacting different leaders across the company and saying “I don’t know you, but I’d love to get to know what you do.” She picked people she knew were a big part of the culture of the organization and set up coffee dates with them. Hilary Rapkin, WEX’s Chief Legal Officer, was one with whom she remembers having a particularly meaningful conversation. Rapkin is one of WEX’s longest standing employees and is deeply invested in the company’s culture and Andrews became convinced after that conversation that WEX was a good fit for her. “Every single person I met in leadership positions was so willing to talk and share ideas, and everyone was open and passionate about what the company was doing. People cared a lot. And that’s huge. They were genuine, and excited and smart people and I thought to myself, ‘These are the kind of people I want to learn from and with whom I want to work and grow.’”

Andrews is also convinced that because she took the time and made the effort to meet and have these fact-finding conversations with people across a broad spectrum of WEXers, when Jay Dearborn, president of the corporate payments division, needed to build his leadership team, Andrews came to mind for some of the people with whom he consulted. She was curious, intelligent and she cared about WEX and maintaining the company’s culture. All of those qualities made her top of mind for many on WEX’s leadership team.

After time spent in corporate payments leading global strategic accounts, Andrews’ role grew in the department. “From there, my role expanded to the whole of the Americas’ Travel and Enterprise Payments and, now, my role as GM of Americas Travel is the start of yet another adventure and opportunity with WEX.”

How following a path of constant improvement can lead to success

With an undergraduate and masters degree, both in Psychology, with an emphasis on organizational behavior and change management, Andrews approaches her work from a unique angle. While others with the degrees she holds may have taken a more conventional path, Andrews’ education, strong emotional intelligence, and innate interest in and ability to empathize with others give her an advantage in leadership and people management.

Andrews describes holding different positions at WEX, sometimes for as little as a year, but just long enough that she could feel she accomplished what she’d set out to do. “I created a knowledge base program with the HR team, because, ‘Why not?’ Made that systematic and handed it off to the training team and then moved on to the next opportunity.” At every turn she would hire or train someone to take her position before departing for the next challenge.

In any given role Andrews always paid attention to the company’s operations at large, to get a sense of ways she could contribute in new and different arenas. “I have a feel for what can be made better and if it’s something that I can influence or not, and that’s what’s fun for me.” This is one reason Andrews continues to form and build relationships with people throughout the company. Andrews has an acute understanding of where the needs are at any given time at WEX. “If I’m going to move across this organization it needs to be to a place where I can do something meaningful and impactful.”

How can young women develop their leadership skills?

Andrews has three pieces of advice for young women interested in developing their career: find your own path to success with an emphasis on having a positive impact and staying true to yourself, consistently network with others across the organization, and don’t be afraid to try things that might not appear to be within your frame of work.

“Get to know what’s going on. Do your job well, don’t get distracted, but look outside your day-to-day work and meet people across the organization. Don’t be afraid to make a phone call and say ‘Can I talk to you about what you do?’ Be curious. Every conversation and networking opportunity doesn’t need to be a quest for the next job. Just be curious.”

As far as being unafraid to try jobs outside of what you think is the “correct” path, some people do take a very straight path through their career, and that’s a fine approach. What Andrews is suggesting is that that is not the only way to find success in your work. In her experience, being open to whatever interesting work came her way was what ultimately led to success, and what made her work enjoyable. “Trust your instincts. If there’s an opportunity to do something interesting but it isn’t what you planned on doing at all, that’s okay. Learn about it, and go for it! And if the door opens, walk through! Give it a try. You can change it up later.”

Current leaders can bring others along through mentorship

According to a Forbes article by Naz Beheshti, Sun Microsystems produced an in-depth case study about the benefits of mentorship programs within organizations and found that:

  • Employees who participated in a mentorship program were five times more likely to advance in pay grade, and mentors made even more progress than the mentees in the study.
  • Mentees were promoted five times more than their peers not participating in the program, and mentors were promoted six times more than their non-mentor peers.
  • Retention rates were significantly higher for mentees (72%) and for mentors (69%) than for employees who did not participate (49%).
Women in Technology - How Mentorships Help Shape Careers
Women in Technology – How Mentorships Help Shape Careers

Andrews believes that current female tech leaders have the most power to elicit gender equity changes in the field. Mentorships are a powerful tool to help create industry change. Andrews believes that formalizing relationships between women in charge and women just entering the field will be essential for the tipping point we need to see happen to be achieved. “An incredible power that current leaders have is their unique ability to reach out and help ‘could-be great leaders’ build key interpersonal connections to give those individuals the opportunity to, when an opening at the table arises, get a chance at that seat. The tendency for leaders to find familiar leadership personas, and like-minded mentees to bring along is a key part of that dynamic. In this way, more women at the table have brought more women to the table by becoming ‘familiar leadership personas’, representing, mentoring and showing other women the way to get there.” The more women already sitting at the table, the more young women just entering the field will be given opportunities for career advancement.

WEX’s Heather Andrews leads with purpose, leaving the world better than how she found it with each interaction. With her drive, intellect and warm and caring leadership style she is a role model to anyone working in technology at WEX, and a great asset to the company as a whole.

To learn more about WEX, a growing and global organization, please visit

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