Rebecca Gregory set her sights on a career in law from a very early age.
“I knew I wanted to be an attorney pretty young,” Gregory says. “I would say fifth or sixth grade, I kind of set my eyes on it. Obviously, I wouldn’t have known for sure that that’s what I wanted to do at that age, but the more I learned about it, the more certain it became.”
Sure enough, Gregory spoke it into existence. Fast forward to the present, and she serves as the assistant vice president of commercial litigation at Union Pacific Railroad. The Harvard Law School product and former judicial clerk has entered her fifteenth year at the Fortune 500 company, where she rose up the ranks of its legal department. She takes on its largest commercial litigation cases while leading a team of legal professionals.
Gregory sets high expectations for herself and her team. “I believe people always strive to meet expectations, whether you set them low or high, so I try to always set high expectations,” she explains.
Since Gregory joined Union Pacific in 2008, she has received promotions to general attorney, senior general attorney, senior counsel, operating chief of staff, and assistant vice president of commercial litigation.
When Gregory first started at Union Pacific, she took on all sorts of cases: property damage, contract, employment, antitrust, and even argued an appeal before the United States Court of Appeals, Eighth Circuit. “I was able to handle cases in-house, which I think is unique. Not many companies have their in-house counsel showing up in courtrooms or arbitration hearings [and] handling the cases personally versus engaging outside counsel to do so, so that’s been an exciting and fun thing that you see at Union Pacific.”
Once Gregory established more relationships across Union Pacific, she started to defend the company in more and more high-profile cases and pioneered a practice within the law department focused on pursuing claims where Union Pacific would be the plaintiff. “I developed a name for myself that I was willing to go into the arena and fight,” she reflects.
Gregory has served in leadership roles in Union Pacific employee resources groups, most recently as the executive director of Lead Educate Achieve Develop (LEAD), which provides professional development opportunities for all employees, but is particularly focused on women. It holds training and workshops on all sorts of topics and is committed to Union Pacific’s goal of doubling the number of women working for the railroad.
“LEAD provides an opportunity, especially for those that are newer to the company, to demonstrate leadership ability that they might not get in their day-to-day job, and also an opportunity to get outside of your department and meet people cross-departmentally with whom you have a shared interest,” Gregory says.
Still, she credits her past experiences for shaping her career success. She was a judicial law clerk at the US District Court of Idaho, where she learned the ins and outs of the legal system under Judge B. Lynn Winmill. Then, she spent four years at Husch Blackwell in Omaha. Within her first twelve months at the firm—let alone as an attorney—she represented clients who were on trial. She explains how the nature of trial leverages her competitive spirit.
“While at the firm, I had some terrific mentors that really influenced me,” Gregory says. “They gave me numerous opportunities to learn, encouraged me, and were hard on me when needed. So, I’m very grateful for the example they set.”
Gregory is far more than just a high achiever who climbed the career ladder; she fosters an upbeat work environment and encourages her team to be more than simply coworkers. “Because you never want to let your friends down, establishing friendly relationships is key,” Gregory says. “You’re going have their back, so I try and foster that camaraderie.”
The lawyer advises attorneys who are less advanced in their careers to never underestimate their potential. “Say yes to every trial,” she says. “Don’t let fear stop you. Be prepared; preparation can often outdo talent. Even if you’re a young attorney, you can generally compensate for your lack of experience with your level of preparation.”