Cherrie Wilkerson

How This Small-Town Girl Transformed Into a Business School Dean

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Key takeaway: Opportunities find you when you grow ~and maintain~ strong relationships 

Top 5% in the world at: Giving my closing speech

Cherrie is our ultimate champion. She embodies poise and confidence, and is passionate about developing impactful relationships. Cherrie now serves as the Assistant Dean for Young Professional Programs at the Owen Graduate School of Management. Highly respected and admired by her students, she was recognized by Vanderbilt alumni as one of the top 10 people who had a special impact on the student experience. She shares the highs and lows of her journey with us, from her days as a small-town girl to her entrepreneurial ventures in consulting.

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How She Did it

I grew up in a little town in Alabama with 5,000 people. You could see all the stars at night because there were no major cities nearby. I knew I didn't want to live in that little town forever. I wanted to major in something that would help me get a job to support myself and do wonderful things. I remember my 8th-grade counselors asking, "If you could do anything, what would it be?" My ultimate aspiration was to be a secretary in NYC. That was as far as I could see from this little town in Alabama.

My family grew up in Tennessee and knew about Vanderbilt, so I only applied to the University of Alabama and Vanderbilt. I got in and went; I didn't even visit campus. I majored in Business and Computer Science because it was an up-and-coming field. It was exciting, and I knew I could get a job if I did well.

Did you have a clear idea of what you wanted to do for a career?
Not really. Perhaps something in the computer field. I interviewed on campus and took a job in Boston working for Electronic Data Systems (EDS) which was computer programming for healthcare companies. EDS trained me in a field I had prepared for, paid very well, and offered geographic flexibility.

Boston was a big adjustment, but it was fun, exciting, and young. I made it my home.

What were you anxious about?
I wanted to do a good job and perform better than everyone else. Therefore, I would do extra things. I created a training manual for people that were teaching me claims processing. The manual was well-received which differentiated me from my class. Honestly, it’s the little things.

However, I soon realized that I wasn't very interested in the day-to-day work. My boyfriend at the time was going to business school and introduced me to the kinds of classes he was taking and the people he met. I remembered flying out of Newark, New Jersey, looking down at all the industrial complexes, and wanting to understand how everything fit together. I fell in love with the idea of business school right away.

Everything I learned in Dartmouth was relevant and applicable; it was pretty magical. We only had 180 in our class, so the environment was very intimate and interactive. The people were interesting and from all over the place: Princeton, Colgate, Harvard etc.

What career interested you at the time?
In school, I enjoyed learning how everything fit together and operating across a wide spectrum of industries and practices. Consulting wasn't concentrated on just finance or accounting. It allowed me to see how everything worked and fit together.

Did you have a mentor in Dartmouth that helped you find a job/discover your career interests?
Yes, my classmate Bill worked at Bain Consulting as an Associate Consultant. We worked together on various projects and he knew I was interested in consulting because I interviewed with McKinsey. I'm pretty sure he put in a good word for me. Working in GE’s corporate strategy department gave me the skills to do well in the Bain interview.

Bain was amazing. I worked with really smart people and learned a lot from them. It was basically a continuation of business school. I remember thinking, "I wish it didn’t pay so well because other people are going to want to do this."

What set you apart from your starting class?
I knew how to program an assembly language, so that gave me a competitive advantage.

What skills did you learn at Bain?
I learned how to manage clients and build a cooperative work environment from a superior who was masterful with clients. He would lead every meeting and facilitate the most ideal outcome for us by having the client come up with the idea, instead of having us preach at them. From him, I learned that the customer is always first.

So why did you leave Bain?
There was a track at Bain in which you worked for 2 years and then you were up for a promotion, which came in first and second waves. Well, I was not on the first list and that was a huge blow. It totally rocked my world. In response, I talked to my manager and he told me that he’d give me a case to manage. If I could demonstrate my ability, then I’d be promoted in the next round. I talked to my client’s product manager and he convinced me that the process was too complex and hopeless. Rather than running toward the sound of the gun — which is a piece of advice I always tell my students — I panicked and quit. I thought I was going to fail, and I'd never really done that before, so I choked. Everybody was on my side and couldn't believe I was quitting. I regret it to this day.

Why was your default to leave and start a new company?
I couldn't think of anything else to do at that point. Everyone's goal at business school was to be a millionaire before they were 30 and retire, which is honestly ludicrous. So I thought, well this is something I control and can do a good job.

My idea was to import quilted pillows from Haiti. I had connections in Haiti, and struck up a business relationship with a company that had been making quilted items. I didn't go about it the right way; I didn't get a team together or have a competitive advantage. I stopped my venture when the sales weren't as strong as I'd hoped and my cash was running out.

How did you find your next opportunity?
I had kept in touch with a classmate, and he and his now wife called me up and asked me to work with them to start Executive Perspectives, an entrepreneurial venture that provides executive education to companies. Unlike my pillow business, Executive Perspectives had all the right criteria: a dedicated team and a strong competitive advantage. PCs were just being introduced and all the technology was working in our favor. I never considered other opportunities because I couldn't come up with a story that would make sense to go back into consulting. I knew the people and knew that I would work hard to make this opportunity work.

We were eating baked beans and struggling while waiting for the payoff down the road. It was so fun to get new business and see the company grow together.

I didn't have presentation and facilitation skills when I started. However, every other week I had to present in front of a group and lead them through our training process. I would watch my peers do it and see what worked and what didn't. I remember one time I was in the back room talking to 2 participants before starting my training session. While I was presenting to everyone, I realized that I connected much better with the 2 that I had built a connection with earlier. I learned that the more personal connection you have with someone, the better they will buy into your speech and materials.

After we sold Executive Perspectives at its category price in 1998, I focused on raising my children.

How did you balance motherhood and your career?
I moved to Nashville in 1987 and my children were born in 1989 and 1991. The company was kind enough to let me work from Nashville while the team was in Boston. I wanted to move to Nashville because of the warmth and the lifestyle. I was able to raise my children because we shared the workload equally between the team; I never felt a personal burden.

How did you find this opportunity at Vandy?
After a hiatus raising my kids, participating in the Smith College Leadership Consortium, and volunteering at local churches, my former Managerial Studies Professor Bill Damon called and asked, "Why don't you come teach a class?" I had stayed in touch with him through Christmas cards and invited him and his wife out to dinner when I first moved to Nashville. I realized that opportunities find you when you grow strong relationships with people.

Why teaching?
I loved business school. I loved the classes, content, and ability to constantly learn. It was a natural fit. A big part of my love for teaching is teaching college students; developing relationships with young people who are eager to figure out the rest of their lives. College is such a pivotal moment; many students come to some clarification about what they're good at, what they want to do, and who they aspire to be.

Advice for Your Career Launch

Buy into the team
Find people who you work well with and who have similar standards. In entrepreneurial ventures, you don't buy into the business, you buy into the team. Businesses might fail, but if you have a good team, you’ll figure it out or pivot.

To grow meaningful relationships, find a common interest
Find something in common and bring something to them. Don't just look for mentors, but rather create a mutual relationship where you're both interested in something (it doesn't have to be business-related). They will get to know you and think of you more when opportunities arise.

Networking is the #1 trait I see in successful students
Connect with faculty members for advice, classmates who can help you, alums with opportunities. Everyone at Vanderbilt is smart, but it’s having the drive and social skills to make an effort and build a relationship with others that really sets you apart. I wish I had known the value of mentors and how to cultivate them when I first started out. I relied too much on keeping my head down and focusing on the job at hand rather than working with mentors to look ahead to my next position and beyond.

Don't stay in a job if you're not learning
You don't want your job to professionally stunt you. Find venues to develop skill sets that are going to get you where you want to go. For example, take what you're passionate about and do it in a nonprofit setting.

Give people praise
One of my great mentors, Bobbie, had an enthusiasm and optimism that was infectious. You couldn’t be in her presence without feeling her glow. She used to wear a T-shirt that said, “Only visiting this planet.” When I did something that she felt worthy of praise, it was lavish. Her positive feedback was extremely powerful, and I learned that people deserve that. You should notice and point out when people are doing something wonderful.

Find something that satisfies your soul, not just your bank account
Early in my career, I wanted to be successful by the world’s standards: having a position of responsibility and money that demonstrated success. What drives me now is making a difference; there’s nothing more rewarding and satisfying to me than that. Having passion and enthusiasm for the work you’re doing is paramount. Passion drives people to learn the skills they need to be successful — it drives them to put in the extra hours and exceed expectations for their work. I’ll take passion and drive over IQ almost every time.