Leslie Gross guides C-suite leaders, families, institutions, and UHNW individuals through crisis, opportunity, and change. She brings expansive networks from senior roles in government service, advocacy, global philanthropy, and corporate social responsibility as Principal and Founder of Advantage Insights (www.advantage-insights.com).
Leslie specializes in advising multi-generational wealth holders, family offices, and foundations seeking to navigate political risk, philanthropic strategy, and governance challenges. She has helped donors design resilient giving vehicles, structure boards, and mobilize capital at scale—whether through rapid-response campaigns, civic infrastructure initiatives, or multi-state coalitions.
Her career spans senior leadership roles across institutional and family philanthropy, with a current focus on bridging divides between these communities for greater social impact.
Leslie has managed over $30M+ grantmaking portfolios, created fellowship programs, and launched donor advised funds as a Division Director at the Open Society Foundations. As Managing Director at The Philanthropy Workshop, she designed donor education journeys, lead the organization in member retention, and advised HNWI donors on designing strategies that balanced vision with both impact and joy.
A former Obama Administration Deputy Assistant Secretary, she’s lead high-performing national security teams during some of the nation’s most defining crises—including Hurricane Sandy, the Syrian refugee crisis, and the Boston Marathon bombing. During her earlier work as Chief Counsel for former U.S. Senate Majority Leader Harry Reid’s oversight efforts, she navigated the global aid ecosystem, uncovering billions in waste, fraud, and abuse during the Iraq war.
A lawyer by training and a convener by nature, Leslie leverages her networks across civil society to help clients turn complex challenges into durable solutions. She is a former USRowing advisory committee member, current Data & Society advisor, and member of the Effective Institutions Project’s board of directors. A native of the Philadelphia suburbs, her greatest joy is as a mother, co-founder of the Hope on Water youth rowing foundation, and as an Eagles fan.
Let us know if you’d like to be introduced to this advisor.
