Rolando D. Rodriguez, M.S., CFRE
For more than three decades, Rolando D. Rodriguez has advised leadership teams and boards navigating growth, transition, and complexity.
He is the founder of Crosspoint 360, an advisory practice that helps organizations align leadership, strengthen governance, expand revenue capacity, and execute ambitious initiatives with discipline and momentum. His work spans healthcare, education, community development, social services, and philanthropy, and includes large-scale campaigns, organizational turnarounds, and complex board-engagement efforts.
Over the course of his career, Rolando has helped organizations secure more than $250 million in philanthropy and institutional support, including during his tenure as founding President/CEO of the Jackson Health Foundation, which he led through transformational growth into one of the nation's leading public hospital foundations.
During his tenure, the organization helped envision and fund the Ryder Trauma Center, Holtz Children's Hospital, and Jackson International. Rolando led a multidisciplinary team of more than 100 professionals, helping elevate Jackson Memorial Hospital's reputation as a global medical center.
Other signature projects include creating the Big Brothers Big Sisters of Miami Foundation and its new headquarters; helping create a new 20,000-square-foot campus for the Friendship Circle of Miami; developing a national campaign for San Francisco-based Breakthrough Collaborative; launching a board and growth plan for PATCHES in South Dade; developing the campaign for the Ronald McDonald House of South Florida; and supporting the national expansion of the Latin American Association of Insurance Agents (LAAIA) and the LAAIA Foundation. His latest initiative is a comprehensive strategic and growth plan for the University of Miami's Master's in Real Estate Development program.
Clients engage Rolando for his ability to connect strategy, governance, fundraising, and leadership dynamics — areas that are often treated separately but in practice determine whether organizations thrive or stall. His approach pairs strategic perspective with practical execution, helping organizations move from aspiration to measurable progress.
He believes organizations grow when leadership aligns around a clear vision, disciplined priorities, and a culture capable of sustaining momentum over time.