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Siobhan Crosby

Director of Donor Relations
Bentley University

Waltham, Massachusetts

As Episode #25, I am so pleased to feature my friend and former carpool buddy Siobhan Crosby, who represents the donor relations & stewardship sector of philanthropy. She is the Director of Donor Relations at undergraduate business school Bentley University in Waltham, Massachusetts, where I lived for over a decade before relocating to Utah in 2018. Siobhan talks about entering nonprofit work by utilizing a career coach, while led to her doing donor relations at Harvard Business School.

Siobhan talks about opportunities that kept her responsibilities fresh, and why she has really enjoyed being on the “thank you” side of fundraising, as opposed to the “please” give, engage, serve on boards, etc. side. “It is so, so important to tell the story of what donor gifts do…It inspires joy and hopefully inspires future giving.”

Halfway through, we pivot to discuss side projects, of which Siobhan has one major tech-support initiative in the works. She discusses the challenges of this inter-generationally-focused project, what motivated her to begin this work, and the passion she brings to technology support, to “help aging people stay a part of the social fabric of our society.” Please visit her website at

At the 31-minute mark, Siobhan and I trade brief stories of our respective side projects; setting boundaries to ensure that we stay focused on our primary responsibilities and our respective families; and continuing to cultivate our curiosities for continued learning. I loved her thinking about this all as “the surfboard of life.”

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