Hilary Rapkin – WEX Inc.

Hilary Rapkin is proud of her nearly 30-year career at WEX, the Portland, Maine-based global commerce platform that simplifies business operations. The Company’s specialized expertise and rich data make it easy for companies worldwide to simplify benefits, reimagine mobility, and pay and get paid. She has significantly impacted WEX since joining in 1996, and she has no regrets. However, her tenure at WEX is not ending the way she envisioned.

Hilary Rapkin | WEX Inc. | Executive Advisor

In December 2023, Rapkin was diagnosed with cancer, sending shockwaves through her, her family, and her WEX colleagues. Within mere days, she underwent major surgery, which involved the removal of a kidney, ureter, and a part of her bladder. It was an uncertain and challenging time, leaving her unsure of the future.

Post-surgery, Rapkin had to confront the harsh reality of her illness. She consulted with several oncologists and eventually underwent 12 weeks of chemotherapy at the end of January 2024. During this challenging period, she had candid discussions with WEX’s Chair, CEO, and President, Melissa Smith, who was notably compassionate and understanding about Rapkin’s situation. Melissa’s constant refrain was concern for Hilary’s health and well-being. The time and space away from work enabled Hilary to concentrate on managing stress and prioritizing her health.

Following three months of rigorous chemotherapy and a month dedicated to recovery, Rapkin returned to WEX in May 2024. While she wasn’t ready to dive back into her previous responsibilities, she took part in important events such as Board of Directors meetings and strategic planning sessions. At this juncture, Rapkin realized a full return to her demanding role was no longer feasible.

“I decided not to return as Chief Legal Officer, and though it was a tough decision, the fact that we had an interim general counsel who was being developed as my successor while I was away made me feel like the company would be in great hands,” Rapkin tells Vanguard during a summer interview from her home outside of Portland.

Feeling that returning to WEX full-time wasn’t the right path for her, Rapkin and Smith discussed her transitioning to an executive advisor role, focusing on specific problems and projects. She plans to stay with WEX in the executive advisor role through the 20^th anniversary of WEX being listed on the New York Stock Exchange in February 2025, ultimately retiring from WEX at the beginning of March. Though different from what she initially expected, assuming the executive advisor role is a solution that allows her to still contribute to the company while respecting her health and well-being.

Winning the fight

Throughout her tenure, Rapkin has significantly impacted WEX and the wider community in Maine. Her career has been defined by her commitment to fostering an inclusive and progressive workplace. She recalls the early days in the late 1990s when gender issues were more prominent. WEX’s culture, under leaders such as Mike Dubyak, the company’s prior CEO, and now Smith, has always been progressive. For instance, Smith assumed the CEO role in 2014 and shortly thereafter became the first female CEO of a publicly traded company to give birth while holding the position. Smith has continued to navigate the evolving landscape of women in leadership roles and has set an example for her peers.

Rapkin has been a staunch advocate for gender equality and has played a key role in initiatives like the Women of WEX employee resource group, which she helped establish eight years ago to support and uplift female employees. Rapkin has spoken on various panels about diversity, equity, and inclusion. She has also been involved with the Olympia Snowe Women’s Leadership Institute, a program created in honor of 18-year US Senator Olympia Snowe to empower women leaders.

“I have always been an advocate for blending professional achievement with personal values,” Rapkin says.

Rapkin says her experiences have also influenced her perspective on work-life harmony, particularly as she managed her career while raising two sons with her husband, who is also a lawyer.

“Balance, or harmony, comes from making a variety of choices, both big and small. I believe that your values guide you in supporting all aspects of your life—family, community, self, and career. The way you prioritize your intentions shifts over time. The idea of wholeness is significant, as we all strive for balance and harmony in our lives,” Rapkin explains.

As she nears the end of her career, Rapkin, 58, says she never intended to work into her 60s, even before being diagnosed with cancer. She is cherishing the time she has left at WEX, focusing on completing projects and sharing her expertise with colleagues on the Legal team and others in the company. She appreciates the flexibility afforded by her advisory role, which allows her to contribute without the relentless pace required of her previous responsibilities. Rapkin hopes she is remembered for her fierce loyalty and commitment to people and culture, innovative leadership, and the indelible mark on WEX.

The legal journey

Rapkin’s path began in a family deeply rooted in the legal profession. Her father, a tax attorney, and her mother, a law librarian, set a foundation that influenced her career trajectory. Following her studies in art history at Bowdoin College in Brunswick, Maine, where she says she developed her critical thinking and analytical mindset, Rapkin initially explored a paralegal role in Boston before pursuing a law degree at the University of Maine School of Law. Although uncertain about her career path, Rapkin was drawn to the legal field’s dynamic nature and the intellectual challenge it provided.

In 1996, Rapkin joined WEX as its first lawyer, a role that would become pivotal in shaping her career. At the time, WEX was a burgeoning company with a modest team of 150 employees. Rapkin’s leadership in building and expanding the Legal team was instrumental in the company’s growth—the workforce now includes around 7,000 employees globally.  “As the team evolved over the years, I made it a point to interview each member, prioritizing talent, expertise, and cultural fit. Finding the right fit is crucial for creating a high-functioning team grounded in respect and trust. I take great pride in the WEX legal team, made up of exceptionally skilled, professional, and genuinely good people,” she says.

Rapkin’s story is a testament to the power of perseverance, the importance of supportive leadership and the impact of fostering an inclusive and dynamic workplace. As she looks forward to a well-deserved break from her career’s demands, Rapkin is excited about the prospect of enjoying simpler pleasures, like sipping coffee and taking in a view without the early morning rush.

Though her career may be winding down, Rapkin’s influence and contributions will continue to resonate within WEX and the broader community she has diligently served.

“I am truly grateful for the opportunity to be part of the WEX journey, and I am excited about what lies ahead. I aim to stay healthy, have fun and continue contributing wherever I can,” she says.