Steve Theobald Is Honest, Humble, and Hungry for a Challenge

CFO Steve Theobald shares how he built his career in finance and how he’s approaching two big challenges he faces today at Walker & Dunlop

Photo: Bryan Blanken/Freed Photography

“When you’re looking back on your career, you can create a nice, tidy story in your mind where everything seemed planned out. But as you’re actually going through life, it doesn’t work that way,” remarks Steve Theobald, executive vice president and chief financial officer at Walker & Dunlop. “The reality of my life and my career is a lot messier than it looks from the outside.”

Messiness aside, the reality is that Theobald has spent the better part of the past three decades working in some of the most coveted roles in the finance industry, first as a partner at a leading accounting firm and later as a senior vice president, executive vice president, and chief financial officer in the in-house departments of Capital One and Hampton Roads Bankshares.

But according to Theobald, he learned many of the life lessons that have been most critical to his career success years before he even enrolled as an accountancy major at the University of Notre Dame.

“I’m the oldest of eight children in a family of relatively modest means, and as the oldest, I learned certain responsibilities pretty early on,” Theobald recalls. “The importance of being focused and goal-oriented have stayed with me throughout my life, both from a personal perspective and a professional one.”

After graduating from college in 1984, Theobald says, he had only one goal in mind: become a partner at one of the big eight US accounting firms. Every step that he took early in his career was an opportunity to learn, grow, develop, and move further toward that goal, Theobald says, including his decision to deviate from the traditional accounting firm career track and accept a fellowship in Washington, DC, in the middle of his public accounting career.

Stephen Theobald
Stephen Theobald, Walker & DunlopPhoto: Bryan Blanken/Freed Photography

“But once I went back to my firm and made partner, I just went, ‘Okay, now what? I’m not going to be doing this for the rest of my life; I’m only thirty-three years old,’” Theobald recalls. “I needed a new challenge, and a new goal, and I decided that I wanted to become CFO of a public company.”

Theobald joined Capital One in 1999 as senior vice president of finance and ended up staying there for more than eleven years. “At that point, Capital One was a relatively small company compared to the institution that it is today,” Theobald points out. “I had so many opportunities to learn about managing an organization—and managing people.”

In 2010, when he joined Hampton Roads Bankshares, Theobald achieved his goal of becoming CFO. But he has by no means been in want of new challenges and goals since then.

Theobald has served as EVP and CFO at Walker & Dunlop for seven years now, during which time he has helped build out the financial services provider’s marketing department as well as its servicing group. In fact, in the time that he has been with the company, Walker & Dunlop has increased its market capitalization from $700 million to approximately $2.5 billion right before the coronavirus pandemic.

“The focus for me is always on overall company success,” Theobald says. “It’s been a blast to have been here during all of that growth, but for me, the question is always, ‘How do we continue to drive that growth in the future or during difficult times in the economic cycle?’ And at the same time that we expand our portfolio, we need to ensure that we continue to provide excellent service to our customers, on both the front end and the back end.”

To ensure this customer-minded growth, Theobald works closely with the internal finance, servicing, marketing, and investor relations teams at Walker & Dunlop as well as with the company’s external partners. But that work does come hand in hand with two significant challenges, Theobald reveals.

Firstly, Theobald notes, is his “bias towards decision-making. Especially earlier in my career, I used to be that kind of person who would just tell people what to do—because at that stage of your career, you’re rewarded for your own individual ability to drive results.

“The importance of being focused and goal-oriented have stayed with me throughout my life, both from a personal perspective and a professional one.”

“But as you progress,” the EVP continues, “you get rewarded for the great work done by the people who are under your direction. That’s one of the hardest transitions you can face in your career: you have this misguided belief that you can do something better or faster than one of your team members—but if you jump in and do it yourself, you’re depriving them of the ability to learn and grow.”

Now, when helping to lead the critical, company-wide risk management programs elicited by the COVID-19 pandemic, he stresses the importance of identifying the areas where one can make a true impact. There are so many unknowns, and it is tempting to channel energy into trying to solve the unsolvable. Instead, Theobald notes that his biggest takeaway from the crisis is to relinquish the illusion of control and focusing on attainable positive change.

“We’re proud to call Steve a client and to provide Walker & Dunlop with critical capital and banking services,” says John Wolff, CRE Real Estate Market Executive for Bank of America. “He is a true leader who inspires and empowers his team, and we thank him for the partnership.”

On other initiatives, such as Walker & Dunlop’s new What Drives You ad campaign, Theobald makes a point of asking questions so that others can reach conclusions on their own.

“I see my role in this campaign as that of a steward, working on behalf of the CEO to help steer the marketing team,” he says. “It’s sometimes a challenge to let go of the reins because every day there is so much going on and so many key decisions that have to be made. But I always remember that even the worst micromanagers I’ve worked for have never known everything that was going on, as much as they tried to.”

“If you grow up humble and treat everybody respectfully, that makes you a people person too.”

Christopher Small has worked with Theobald for the better part of ten years, and notes that he is consummate professional in every sense of the meaning. “His approach to his craft and the manner in which he treats his colleagues and business partners is always with utmost integrity, honesty, and transparency,” says Small, head of diversified financials for FIG Corporate and Investment Banking at Wells Fargo. “I’ve always been impressed with his poise and calm in difficult times and how he is grounded during the best of times.”

The second challenge Theobald faces every day at Walker & Dunlop is far more personal, and in some ways, more difficult to address.

“By nature, I’m really more of an introvert—I’ve never really liked larger social settings,” the EVP admits. “But early in my career, I realized that to be successful, you have to be able to work a room. You have to be able to speak to a large audience. So I intentionally volunteered as an instructor for new staff members, which put me in front of a group of about thirty people.

“Talking to them about the ‘latest and greatest audit issues’ was a way for me to begin overcoming that fear,” Theobald recalls with a chuckle.

Now, of course, Theobald works with people all the time. “Whether he’s empowering his staff or applying empathy and integrity to key business practices, it’s easy to see how Steve’s thoughtful leadership makes a daily impact at Walker & Dunlop,” says John Harvey, senior vice president for PNC Real Estate.

But even today, Theobald notes, socializing is not necessarily easy. “When I have to go to an all-day investor conference and talk to people for eight straight hours, those are the most exhausting days for me,” he says. “But I’ve worked hard at being as comfortable as I can in those settings.

“And maybe I’m not a gregarious, backslapping kind of guy,” Theobald adds, “but I do treat people well at all levels of the organization. And I think that if you grow up humble and treat everybody respectfully, that makes you a people person too.”


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