We’ve all met people who were born on third base and act as though they’d hit a triple. They never acknowledge the reasons behind what got them where they are.
Cunningham grew up on the South Side of Chicago,” in the same South Shore community where Michele Obama once lived. When her birth parents lost custody of Cunningham and her siblings, they were taken in by family friends who taught them the importance of faith, family, and education.
When circumstances changed, however, Cunningham and her siblings had to fend for themselves, but thankfully they also had a great deal of assistance from members of their church.
“My brother, Keith, dropped out of college so he could help care for me financially,” she recalls. “He and my older sister, Sharon, really played pivotal roles in my teen years. Keith later became a successful businessman and minister, and my sister is now a teacher.” Cunningham and her siblings would later learn of an older fourth sibling, Karen Adams, who has also become an important part of their lives.
After graduating from Hyde Park Career Academy, Cunningham earned a bachelor’s degree in industrial engineering and management sciences from Northwestern University. At Northwestern, she met her “brilliant and supportive” husband of twenty-five years, Jason.
Following her college graduation, Cunningham earned her JD from Creighton University School of Law. “Moving into law wasn’t as big a stretch as you might think,” she says. “I’ve always seen similarities between the two professions. Lawyers are like social engineers, trying to solve problems and mitigate risks.”
Originally, Cunningham was shepherded toward patent law because of her technical background, but she soon discovered it wasn’t for her. “I wanted to practice in areas that were more people-centric,” she says. Her rationale for going in-house was simple: it would enable her to function as a strategic partner within an organization, interacting with many people across various disciplines.
Cunningham began her legal career in 1998, as a logistics property manager for Sears Roebuck and Company, where she devised strategic initiatives for the real estate property portfolio. Her next career stop was the Northern Trust Company in 2000, where she served as second vice president of trust real estate services.
In 2007, she became a compliance attorney for the Walt Disney Company followed by a nearly six-year stint as general counsel and director at international franchisor DirectBuy. Finally, in 2019, Cunningham joined National Express, a premier transportation firm based in the United Kingdom.
Her decision to join National Express was based upon having the opportunity to work with two of the “brightest legal minds” she had ever encountered, General Counsel Dorothy Capers and Deputy General Counsel Djenne Clayton. Cunningham credits the attorneys for having advocated for her professionally in an exceptional manner. She reached her professional pinnacle in early 2022, when Capers told Cunningham she’d be assuming the GC spot for the company.
“I really didn’t expect that to happen, but I felt proud for having earned the opportunity as well as extremely grateful,” she recalls.
Cunningham and her “uber-talented” team of twenty-four provide legal advice and guidance across National Express’s activities in thirty-six states and several Canadian provinces. While those activities are limited to school, transit, and shuttle bus services, her plate is full.
“We handle litigation, employee relations, and unions, including collective bargaining, negotiations, grievances, insurance, and workers compensation,” she explains. “We are also involved in the company’s real estate dealings, such as bus depots, as well as contracts with customers and vendors, environmental matters, and the governance aspect of about 150 corporate entities.”
And while some legal groups earn the nickname “the department of no,” Cunningham takes a more positive approach—explaining why a proposed action might be detrimental to the company, and how to find the best possible course of action. “When you distinguish yourself that way, business partners come to you before there’s a problem,” she attests. “They understand that you have a vested interest in their success and can make informed decisions based on your advice.”
The legal landscape for the transportation industry is constantly changing, so her group is overseeing several initiatives to stay abreast of shifting situations. “We’re constantly working to support operations from a contractual perspective and in implementing corporate policies and changing regulations that impact our business,” Cunningham explains. “We work to provide the business with education and tools to protect our interests.”
Perhaps even more complex are compliance projects that have far-reaching implications. Because National Express’ parent company, National Express Group PLC, is publicly traded in the UK, the US operation must abide by many of those regulations, as well.
“There are antibribery specs that cover procurement and other activities and there are global policies that address matters as compulsory labor that must be considered,” Cunningham says. “Everything must be spelled out in contracts with our vendors. Additionally, we must support the business operating in accordance with our company’s ethical values and in being a good corporate citizen.”
The company is also making a special effort to monitor union environments in order to keep drivers behind the wheel.
Cunningham manages her hard-working team by relying on a concept she learned from a Disney executive: RAVE (respect and value everyone). “I have regularly scheduled meetings with my direct reports, but I also sit down quarterly with their direct reports. It helps me understand how things are going and lets me gauge the current company mood and culture,” she says. “It also gives me ideas on initiatives I can implement to better support our business and create a better work environment for our team.”
Her collaborative team works in a congenial atmosphere, and Cunningham wants them to feel comfortable coming to her for guidance or advice. They often have lunches together to discuss life inside and outside the office environment.
“The team is supportive of one another, and we try to celebrate milestones and accomplishments on our Microsoft Teams channel,” says Cunningham. “This year, we were fortunate to do a team outing working at a local food bank in one of the communities we serve. Our goal is to participate in at least two charitable events annually.”
“Skilled and dedicated team members are a hot commodity,” she notes, “and it’s the most important component of our organization. So, I tend to expect the best of people, rather than assume the worst. It comes down to treating them the way I’d like to be treated.”
While there’s no guaranteed path to success, Cunningham offers some tips to improve the odds. “Use every opportunity you can to add to your professional tool belt because, as in-house counsel, you’re going to need every one,” she advises. “Be assertive. Run towards special projects, not away from them. When hiring, surround yourself with teammates who will challenge your thinking, rather than simply and mindlessly agreeing with you. This will create the best environment for growth.”
And, perhaps most importantly, she adds, “As general counsel, it is imperative that you serve as a core and active member of the senior leadership team, contributing beyond the legal remit. You must add insight and challenge to commercial topics in order to impact key decision making.”
“Congratulations to Steffany Cunningham on her well-deserved recognition by Modern Counsel. She has excelled in her position as GC for National Express North America and is the consummate team leader.”
—Daniel Cohen, Partner
“Steffany brings a dynamic blend of creativity, grit, intelligence and practicality to her approach. She is committed to the success of National Express and her legal team, and partnering with her is a privilege.”
—Michael D. Thomas, Principal