S03 E11: Tiffany Benjamin, CEO, The Humana Foundation
Meet Dan Florness
Tiffany Benjamin is the CEO of the Humana Foundation, the philanthropic arm of one of the country’s largest healthcare companies. A Harvard-trained lawyer, she began her career at a major firm, served as senior investigative counsel for the U.S. House of Representatives, and rose through Eli Lilly’s legal ranks before leading the company’s foundation and social impact work. Since becoming CEO of the Humana Foundation in 2022, she has focused its work on mental health and food security for seniors, school-aged children, and veterans, co-founded the national veteran suicide prevention initiative Face the Fight, and earned a place on the TIME100 Philanthropy list.
What sets Tiffany apart is the pairing of deep personal empathy — learned at the side of her social worker mother during the HIV/AIDS epidemic — with an insistence on running philanthropy like a business: measured, accountable, and honest about failure.
In this episode, we cover:
The childhood experiences that made empathy the core of her leadership
The Equal Justice Initiative internship that helped free a wrongly imprisoned woman
Why she narrowed the foundation’s focus — and says no to great organizations
How standardized metrics and 3–5 year grants prove whether dollars move the needle
What health equity looks like in practice, from rural health access to veteran suicide prevention
Why philanthropy should take risks and talk about failure the way business does
The connection between social drivers of health and workforce participation
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