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Dexter Bailey, Senior Vice President for Advancement, Stony Brook University

From his beginnings in politics to his ascent on the higher education fundraising ladder — first at Ohio University, then University of Washington, UC Berkeley, Worcester Polytechnic Institute, and today at Stony Brook University — Dexter Bailey has planned for and achieved success at every turn. Here, he shares with LOIS L. LINDAUER SEARCHES (Lindauer) some of the beliefs that have inspired him throughout a stellar career.

Lindauer: You started out in marketing and communications, and served as press secretary for the Democratic Caucus in the Ohio House of Representatives. You left that job for your first position in development, at Ohio University, your alma mater. Why did you make the switch?

Dexter: Actually, my communications background is what provided me with the opportunity to transition. Prior to going to the Ohio statehouse, I was the number two communications director for the attorney general statewide race. That was a very focused role, one that was all about vision and changing Ohio for the better. So I went into the statehouse with a very idealistic perspective on how we could improve Ohio and change the world.

It became obvious, pretty quickly, that special interest was driving the agenda, whether you were on the Democratic or the Republican side. I became really frustrated that there were a number of things we didn’t move on for a variety of reasons. I decided that I wanted to make a bigger contribution.

Around that time, I received a call from a friend who was the Assistant Dean for Advancement in the College of Communications at Ohio University. He told me about a job for the alumni association at Ohio University that was a perfect match for my communications and marketing skills. It ended up being one of the most rewarding experiences anyone could have. I think what we do in higher ed is actually a pretty special thing, furthering education with some of the smartest people in the world.

Lindauer: What made it so rewarding?

Dexter: What I noticed working closely with fundraisers is that they were taking the relationships and moving them into something really substantive. Even though I was in the alumni office, I developed friendships with a lot of the fundraisers, and started understanding what they were doing and the impact that they were having. It didn’t take long for me to want to move onto the frontlines.

Lindauer: When you first entered the development field, what do you wish you had known — and would it have led you to do anything differently?

Dexter: I think that the fact that I didn’t know much about it when they gave me the chance to be the Assistant Dean for Development in the College of Education was probably a huge blessing. I walked into a program that had been without a fundraiser for about a year-and-a-half. We had a new dean who had next to no fundraising experience, and the college itself was a little challenging. I just knew that I had to raise money; I knew I had to build a campaign committee, and I just did the work. Not knowing a lot probably was a huge asset because I took on everything pretty aggressively and we were able to have one of the best fundraising years for that college, which at that time was a little over $400,000.

Lindauer: How did you do it?

Dexter: We built our campaign committee. I hired a graduate student and we started an alumni newsletter. It was just me and the dean and my office was next to his. They literally renovated a storage closet for me. I didn’t have windows, but I was next to the dean, and we just did it. I learned a tremendous amount because the dean also included me in faculty governance issues and strategic planning. And so my naiveté was probably my biggest asset, because I did not know what I did not know… and projects in-line with our goals all seemed possible.

Lindauer: So maybe there’s nothing that you wish you had done differently.

Dexter: For me, I was excited to get a chance to prove myself as a fundraiser. I’m sure I made a ton of mistakes, but I wouldn’t say that I regret anything from that experience.

One of my donors was a College of Education grad and chair of the Ohio state banking association. I was able to close a significant gift with him and was also trying to get him engaged as a volunteer. He agreed to come to campus, but said, “There’s one thing that I require.” I asked, “What?” He answered, “Don’t waste my time,” and I vowed not to.

That person has actually become a very, very large donor to the university and was also appointed a trustee by the governor. I hear that donor in my head all the time. He taught me a really positive, amazing lesson that I still live by today.

Lindauer: What, if anything, surprised you about the job when you first became CDO at Worcester Polytechnic Institute (WPI)?

Dexter: One was the transition from lead fundraiser to chief development officer. Everything that I had done in my career, from when I started at Ohio University until I got to WPI, was about being the Director of Development and fundraising and making the metrics. When you transition from that into the Chief Development Officer role, there are some aspects of the job that no one tells you about. For example, the title itself denotes a certain level of influence, not only within advancement, but across campus. I think that was one of my surprises because while everything that I had done to bring me to that job was still necessary, I also had to learn new skill sets to be in the C suite as an executive.

Lindauer: What exactly are the skill sets a new CDO has to acquire?

Dexter: When you’re in that seat, you’re not only presenting the fundraising performance numbers, you’ve got to share the strategy that’s led you to that point. You have to think about how to incorporate other members of the president’s cabinet into what you’re doing, especially when you’re running a campaign, because you need the entire leadership team to make the campaign successful.

The second biggest surprise for me was the transition from being a road warrior to really understanding that my primary job is managing this entity. That means generating X amount of new revenue, managing the foundation board and the corporate board, and also delivering on the responsibilities that my boss is giving me. Many times when you become the Chief Development Officer or Vice President, there are things that you’re assigned that go outside of your purview of fundraising.

The third surprise had to do with the amount of time spent on staff development. I’d always been a self-initiating, self-starter type person, and suddenly was responsible for this big team made up of all types of personalities. The team is spread out, usually, across campus, so you don’t have a daily influence on people. You have to figure out how to build a culture with this literally decentralized environment. That was another opportunity for growth that I didn’t necessarily anticipate going into the job.

Lindauer: What traits do you possess that account for your success and your ability to lead?

Dexter: I would break it down into a couple things. My parents are immigrants and they gave us a strong work ethic. I definitely come from a background where you just work until the work’s done. If someone asks, “How long are you working today?” your answer is: “I’m working until I’m done.”

When I was interviewing for the job at Ohio University I remember being advised that, to succeed, “All you’ve got to do is use your common sense.” That’s something I try to do all the time, too. For the programs I’ve managed, we’ve had to be frugal, we’ve had to innovate, we’ve had to, many times, build a culture of philanthropy amongst alumni and friends. I think using your common sense and thinking about things from the donor’s point of view leads to success. I also strongly believe in keeping a very strong focus on the basics. Fundraising 101 still applies whether you’re at Stony Brook, Stanford or a small community college. We have to be excellent and almost flawless at the fundamentals of this business. If we can build a culture where that’s in place, then I think you can do a lot of playing on the fringes and take all kinds of risks.

Lastly, the most important thing is having good people around you. They’re intelligent, they’re going to help you make better decisions, they’re going to pick you up when you’re down, and they’re going to push you higher when you’ve done something well. I think that’s a key part of anybody’s success, having the right team.

Lindauer: What would you say has been a low point in your career and how did you rise above it?

Dexter: The low point is when you’re working really, really hard and your team is busting their butts and your boss only wants the money and your peers don’t value what you do. That happened to me one time and I won’t let it happen again. I take responsibility for it because maybe I could’ve done a better job of managing up. I’ve never measured success by the amount of money I’ve raised, but rather by the relationships that I make. To know that I could easily make a call and still have connections, whether it’s with past donors or staff, is what helps me rise above any negativity.

Lindauer: You’re the face of fundraising at Stony Brook; it’s a big job with a lot of moving parts. How do you manage it?

Dexter: I think time management is really key because the truth is you have to be present. The only way to do that is to manage your time so that not only are you able to meet the donors, but you can also do the things that are expected of you on campus and with your team. At Stony Brook, we take time out to build operating plans for the upcoming year. We think about our goals and objectives, and we work really hard to try to stay focused on those goals and to communicate them.

This is not a job that you can do nine-to-five. I think people who want to be successful have to come grips with that. I know that some people struggle because they may not be in a situation to commit the time that’s necessary to make this work. But to be successful you have to put people first, whether that’s a donor family calling you at 7:00 at night because they have a son that’s in the emergency room or a donor that calls and says I can’t meet this week but I can meet you Sunday afternoon at 3:00. The answer needs to be yes and my team knows that a donor, or prospect, always trumps everything else. You have to have that prioritization. I think that sometimes development officers get confused about their roles and they become graphic designers and they become special events people and they become psychologists to their deans and they become people that are sitting in committees for academic innovation and that’s all great and good, but if you lose sight of the real goal, you’re going to fail.

Lindauer: Work-life balance is a topic of great interest to those in development and advancement. What advice can you offer for achieving that?

Dexter: I take what I can get and I do the best that I can. I’m very fortunate that my wife can stay at home with our kids; there’s a lot of comfort and security in that. The other thing that helps is bringing my kids to campus. We go to lectures together, we go to the Center for Performing Arts together, we take advantage of the opportunities a university — like no other job in the country — offers. It’s a chance to make your family a part of your work. The higher ed environment, if you want it to be, is very flexible because it’s really a culture built on academic freedom.

Lindauer: What advice would you give to aspiring CDOs?

Dexter: I would say two things: One, take time to plan your career. In 1998, I made a plan to be a vice president of a top 100 ranked institution before I was 40. I got there at 36. You need to strategize your course; otherwise you will not have control of your career.

The second thing is this: Your boss matters. Who you work for is critical. I think, sometimes, development officers make decisions based on perceived prestige at the institution, and/or money. If you’re making your decision because you think people are going to be impressed with that kind of resume, you’re probably setting yourself up for failure and unhappiness. Who you work for matters, the priorities matter, the institutional vanity matters, the institutional culture matters. Take enough time to ask yourself: “Is this the right environment for me? Can I succeed here? Do I want to be here?”

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