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From the White House Podium to the Red Umbrella
She was Hillary Clinton's press secretary at 27, built a women's financial business inside Citigroup, and now runs marketing for one of America's largest insurers. The through-line is a stool with four legs and a plate of spaghetti.
Jean Smart
Jean Smart is the founder and CEO of Penelope, a New York fintech rebuilding the retirement recordkeeping layer for the small and micro-businesses Wall Street forgot. After a 20-plus year career as a financial-services executive at Charles Schwab, TD Ameritrade, Citigroup and UBS, she left a managing-director seat to build affordable, fully-digital 401(k) infrastructure for solopreneurs and mom-and-pop shops. The company, which she named after her daughter, launched in 2022 with a mission to put generational wealth-building within reach of the workers institutions have historically overlooked.