Gilbert Bailey

Class of 1991
Posted: August 11, 2014

Gilbert Bailey '91, a Charleston, WV native, was a high school student looking for an opportunity to make something happen, but he didn’t know he would find that opportunity at the Charleston Civic Center.

Alongside his classmates, Gilbert boarded a bus headed for a college fair at the civic center. Most of his friends had early admission to colleges across the country and Gilbert hoped to find where he belonged.

“I heard Guilford College was the best school at the fair,” Gilbert says. “I was immediately drawn to Guilford’s multidisciplinary approach; the idea of learning multiple subjects was very attractive to me.”

Gilbert, the first person in his immediate family to attend college, was convinced that Guilford was where he belonged. However, he had to first convince his mother that a liberal arts college would create more career opportunities for him in the future rather than attending a public, in-state institution.

“I came from a single-parent family and it was a difficult sell to my mother,” Gilbert says. “Instinctively, I knew going to a liberal arts school was going to give me an interesting perspective on the world.”

Gilbert seized his opportunity and enrolled at Guilford College.

“My thought was always that, in an undergraduate experience, you should go to a small institution where you can be a big fish in a small pond versus the other way around,” Gilbert says. “Intuitively, I thought that might empower me, or give me the confidence to go out and do greater things.”

At Guilford, Gilbert became involved in various clubs and organizations including Community Senate and the College’s radio station, WQFS. Through those experiences, he learned the importance of community collaboration and felt empowered to voice his opinion while learning from the opinions of others.

“Through that process, and a little bit of friction, you may come to another point neither of you thought of in the first place,” Gilbert says. “That process doesn’t occur unless you speak up. If you poke reality with your piece of the truth and reality pokes back with its piece of the truth, something happens.”

Gilbert continued poking reality when he graduated in 1991. The USSR collapsed months after Gilbert earned his degree in political science with an emphasis in Russian Soviet studies. At the same time, a deep recession had impacted the U.S. economy and Gilbert had to rethink his plan for life after Guilford.

“I had a friend who was a technical writer at IBM and I thought that’d be cool,” Gilbert says. “I started to apply for jobs and got some direction, but in ’91 there was a recession and nothing was happening.”

He believed moving to Charlotte after graduation might provide more opportunity for him in the technology industry. It took a few months, and many tables waited, before he found that opportunity.

Gilbert was hired as a salesperson for Software Express, a startup software reseller licensing company, and quickly moved up the corporate ladder because of his undergraduate experiences. His job was to sell software to school systems across the country and eventually, as it grew, to manage a sales force and write partnership and licensing agreements.

“At that time, you couldn’t hire a lawyer that knew how to write a partner agreement for software in Charlotte, so you did it,” Gilbert says. “You might have to write a partner agreement by tomorrow.”

Gilbert’s ability to write quickly was an asset to a startup company like Software Express. He recalls his experiences in writing-intensive courses at Guilford and how they prepared him for his career. “We had to write all the time,” Gilbert says. “It wasn’t just in my core major, and I wasn’t even an English major.”

Gilbert said the College also empowered him to speak as a 22-year old employee in company meetings.

“I didn’t think I needed to sit there and let someone else figure it out,” Gilbert says, “I needed to speak my mind and listen to their point-of-view. Between the three or four of us, a result would come out of there and because you participated, when the company grew, you were continually included.”

Gilbert left the company in 2000 and started his own vehicle-leasing software company and a fencing equipment company that imported equipment from Budapest, Hungary.

In 2009, Gilbert joined Beanstalk Data, a Charlotte-based Business-to-Consumer CRM company. As executive vice president, he continues to do most of the heavy lifting on writing agreements for Beanstalk Data, but now it’s for the company’s own intellectual property – a more difficult challenge.

“Often, I get a call from a prospective client that says I need x by tomorrow and you have to write a 10 or 12-page paper by tomorrow,” Gilbert says. “It’s like writing a paper for a class, but it’s for a client.”

Gilbert’s success as a liberal arts graduate in the technology field isn’t uncommon.

“Having been in technology all my life, I see that liberal arts is critical to innovation,” Gilbert says. “Innovation occurs by breaking things apart and putting them back together in better and more useful ways. Now I realize that a lot of the success in technology has come from that liberal arts background.”


Gilbert is a member of Guilford College’s Board of Trustees.

In 2013, Beanstalk Data was recognized as the 10th-ranked company on the Charlotte Business Journal’s “Fast 50” list – a list of the region’s fastest-growing privately-held companies. Beanstalk Data has rapidly grown to become a popular technology provider to quick service restaurants and fast casual dining providers such as Taco Bell, Panda Express and Carl’s Jr. While at Software Express, the company earned back-to-back mentions on the Inc. 500 list – a list of the fastest-growing private companies in the United States (#337 in 1994 and #325 in 1995).

Last Updated: August 12, 2014