Rolando D. Rodriguez, M.S., CFRE
For more than 35 years, Rolando Damian Rodriguez has led high-impact fundraising campaigns, built sustainable revenue systems, and advised nonprofit organizations through periods of growth and transformation. His work spans healthcare, education, social services, and international humanitarian initiatives, generating hundreds of millions of dollars in philanthropic support.
In 2012, Rolando founded Crosspoint Philanthropy, a consulting practice providing strategic planning, board development, and fundraising advisory services to nonprofit organizations nationwide. While rooted in South Florida, his work extends across the United States and includes international healthcare development initiatives in Latin America and the U.S.
Previously, Rolando served as President and CEO of the Jackson Memorial Foundation, where he built what became the nation’s most successful public hospital foundation. During his tenure, the organization raised more than $200 million for signature initiatives including Ryder Trauma Center and Holtz Children’s Hospital. He led a multidisciplinary team of more than 100 professionals across major gifts, grants, project management, international development, and donor experience, helping elevate Jackson Memorial Hospital’s reputation as a global medical center.
Rolando is also the founder of the International Kids Fund, which raised millions to provide life-saving care to critically ill children worldwide. As the founding Executive Director of the Catholic Health Foundation, he helped fund new healthcare programs for the Archdiocese of Miami, including one of the nation’s earliest residential facilities for people living with AIDS.
Among his signature projects, Rolando led the creation of the Big Brothers Big Sisters of Miami Foundation, recruiting a high-impact board, launching new grant and membership programs, and driving consistent double-digit fundraising growth. His work also includes a $16 million capital campaign for the Friendship Circle of Miami, development of a national fundraising office and multimillion-dollar campaign for the Breakthrough Collaborative, launching a new development effort and campaign for PATCHES in South Dade, and a $30 million-plus campaign for a new Ronald McDonald House of South Florida. In 2025 and 2026, he has focused on a comprehensive strategic planning and growth initiative for the University of Miami’s acclaimed Master’s in Real Estate Development program.
Rolando is widely recognized for building influential boards, donor leadership groups, and recognition programs that form the foundation of sustainable fundraising growth. His expertise includes donor strategy, peer-to-peer fundraising, high-profile events, branding, and institutional positioning.
A skilled strategist, writer, and speaker, Rolando is a contributor to Advancing Philanthropy magazine and a regular columnist for AP Perspectives, where he writes on “Myths in Philanthropy.” He has served as President of the Miami Chapter of the Association of Fundraising Professionals and on the National AFP Foundation Board of Directors.
His honors include induction into the Miami Dade College Hall of Fame and recognition in Brickell Magazine’s 2024 “Angels Among Us” issue.