RAISE podcast: Dexter Bailey, Caltech

On this episode of the RAISE podcast, Brent chats with Dexter Bailey, Jr., Vice President for Advancement and Alumni Relations at Caltech. 

Dexter reflects on his family’s emigration from Jamaica to Ohio, his full-ride photojournalism scholarship to Ohio University, his early career in politics, and how his drive for excellence led him to join a small group of people who are changing the world (literally). 

Catch the full episode below.



A few highlights from the episode…

  • Dexter’s father was a prominent politician in Jamaica. His family fled the country to avoid political persecution, and they landed in Toledo, Ohio where they were one of the only Black families in a predominantly white, Polish neighborhood. 
  • One of Dexter’s high school teachers encouraged him to submit to an annual photojournalism competition for minority students hosted by Ohio University. Dexter entered the competition, won, and received a full-ride tuition scholarship to Ohio U.
  • At Ohio U, Dexter and a group of friends sat discussing their first-semester GPAs. When it came his turn to share, he could have lied about his low GPA, but he didn’t. He reflects on this decision, saying “Because I didn’t lie, my friends realized, ‘Hey, we can help. We can be a part of Dexter’s journey.’ “
  • Dexter took his first job in Alumni Relations at Ohio U to escape his position as Press Secretary during a rocky political climate in the Ohio House of Representatives. Reflecting on that transition, he says that he “had no idea that these types of careers existed. It never crossed [his] mind that there were these professionals that worked in higher education that had these dynamic and impactful jobs.” 
  • Dexter worked with a first-time dean, James Heap, to build the Ohio University School of Education’s first fundraising program. They beat their numbers in their first year. “It kept getting more interesting, harder, tougher, and that just motivated me more and more. When I looked at the leader board, I wanted to be at the top.”
  • On one of his first prospect meetings, Dexter met with an alum who was the head of a local bank. The alums said, “Dexter, I enjoyed our meeting and I’d like to see you again, but please don’t waste my time.” At every future meeting, Dexter came prepared with a specific plan to put on the table. The alum gave a first-time, six-figure gift and now serves on the Board of Regents. 
  • Dexter learned a lot from his position working in athletics fundraising at UC Berkeley. He reflects on athletic director (and olympian) Steve Gladstone’s expectation of excellence and the “first-in, first-out, sleep-in-your-office” environment that drove their fundraising success.
  • Dexter says that fundraising is deal-making. And, that just like in all negotiations, “good deals happen when both parties are committed and feel good about the deal.” He reflects on some good deals and bad deals that he’s been a part of in his fundraising career. 
  • Prior to joining Caltech, Dexter’s specialization was “going in and building. At Caltech, this is the first position that’s all about optimizing.”

More about Dexter… 

Dexter A. Bailey Jr. is a fundraising executive with over 25 years of experience. He is recipient of the 2019 CASE Commonfund Institutionally Related Foundation Award. His expertise includes reengineering comprehensive fundraising programs, complex principal gifts, grateful patients, alumni relations, staff development, and organizational optimization. Dexter often speaks on issues related to campaigns, institutional leadership and the role and experience of minorities in university advancement.

Prior to joining Caltech in July 2019, Dexter served for 8+ years as senior vice president for advancement at Stony Brook University and executive director of the Stony Brook Foundation where he spearheaded the most successful campaign in the history of the State University of New York (SUNY) system. He successfully managed development and alumni relations programs at Worcester Polytechnic Institute, University of California at Berkeley, University of Washington, and Ohio University.

Want to help Dexter optimize (and literally change the world) at Caltech? Connect with him on LinkedIn, or via email at dbailey@caltech.edu.

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