Voice of Experience: Hilary Rapkin, Senior Vice President and General Counsel, WEX

By Cathie Ericson

Life is a series of stages, says WEX’s Hilary Rapkin, an observation she was recently reflecting on as advice given to her by a mentor. That means what you feel like when you have a six-month-old baby is not what you’ll feel like when that child is two or four. Life changes, and you can’t base career decisions on those emotions you feel at the start, she says.

Over the years Rapkin has been able to cultivate relationships with professional women in similar stages so they could share common experiences — whether about babies, teens or elderly parents– all in an effort to have a rich life and find the elusive work/life balance. That vision and support is how women can successfully integrate a high-powered career with family, she says.

A Serendipitous Interview Launches an Illustrious Career

After law school, Rapkin joined a boutique firm in Portland, Maine, where she soon found that law firm life, specifically litigation, wasn’t a good fit for her. However, she realized she could parlay the employment discrimination work she was doing into a potential career in HR. While interviewing with WEX, the HR director noted that Rapkin’s experience was a better match to a legal position – one the company was considering creating. She was hired and has spent 22 years at the company, growing from a one-person legal department to today, where she oversees the company’s global legal footprint and has HR reporting directly to her.

Among the many noteworthy experiences she’s had over the years, Rapkin considers her involvement in WEX’s IPO in 2005 to be the professional achievement she is most proud of thus far. The team accomplished the filing in three months – while she was pregnant – and she remembers the fast learning curve as being particularly exciting.

Aside from that, she says that over the past few years she has been involved with the HR function, she has found it extremely satisfying to watch the evolution of cultural elements that make WEX special. “The process that has made our culture so strong has been very intentional, and some of the HR programs, such as philanthropy, have had a meaningful impact on employees that may be hard to measure, but you know it when you see it,” she says. “It’s made me really proud of who WEX is and how it is becoming visible to the outside world.”

She looks forward to seeing how WEX can continue to move forward along that trajectory, and to watching the forward-thinking programs and compensation plans come to fruition.

On the legal front, she is pleased to see investments in technology which will create efficiencies and opportunities for legal staff to develop deeper advisory roles with their clients. The new systems are designed to simplify core processes like contract maintenance in an effort to free up associates’ time for more strategic work, such as building business relationships and helping WEX achieve its business objectives. “It’s hard to work on becoming a trusted business partner if you are mired in contract work, so I look forward to seeing how these additional systems will help our team.”

As the department has grown, Rapkin has become an expert on new business segments, as WEX has moved into the broader payments landscape. She finds that 22 years later, her job is still challenging as she works through evolutions in technology and the complexities that a global payments company present.  She thinks future lawyers will have similar interdisciplinary experiences as law schools couple with business and finance functions to groom lawyers who are more well-rounded when they enter the field.

An Environment Dedicated to Success

While Rapkin never took psychology, she remembers taking the Myers-Briggs personality test. This led her to think about who she was compared to peers, and the effect those different personality styles had on their relationships.

“By knowing your relative strengths and weaknesses, you start realizing that it’s the sum of the parts that makes companies successful, and you don’t have to have the weight of the world on your shoulders,” she says. “It’s important to figure out how to get the best out of your team by managing each individual as an individual.”

She’s proud of the strides WEX has made in implementing programs that she says are a clear depiction of the company’s commitment to offering choices to both women and men, including paid parental leave, which only 17 percent of companies offer. “I hear from people all the time about how that sets us apart, and certainly our profile as a diverse company is bolstered by having three female members on the executive leadership team.”

Rapkin is poised to launch an informal women’s group this summer that will encourage them to learn from one another through informal dialogue around topics like networking, perceptions of women in the workplace and goal-setting.

Gender equality is just part of who WEX is as a company so Rapkin has never felt any gender bias. She does note that sometimes it’s hard to balance parenting and work, although she stresses that her work has ultimately made her a better parent.

A Commitment to Balance

Rapkin takes every opportunity to do yoga as part of her quest for balance, and also counts philanthropy as an important component towards that end. She enjoys bringing her kids, ages 15 and 12, with her to volunteer at a local Jewish nursing home, and is also on the board of a local theater company that often produces original works.

Her kids have inherited her love of adventure, having traveled since they were babies. “We live in a beautiful place, but I want them to see the world,” she says, adding they are looking forward to a summer trip to Chile.

She is also quick to mention that she doesn’t do it all herself.

“I’ve had the same nanny for 15 years; she’s part of our family, and I couldn’t be successful without her. In life, at home and at work, you get out of relationships what you put into them.”