Former Square Executive Becomes Billionaire As Stock Surges

Veteran technology leader Jacqueline Reses is a new billionaire after shares in Square, the financial services firm where she served as an executive for five years, continued climbing this month.

Reses ranked No. 30 on Forbes’ latest ranking of America’s Richest Self-Made Women, published earlier this month, with an estimated net worth of $920 million. She has now crossed the $1 billion mark, owing largely to her 0.4% stake and additional stock options in Square. The San Francisco company’s stock closed at $267.57 per share on Wednesday, 22 times higher than the $12 a share at which it debuted on the New York Stock Exchange in 2015. The payments giant now sports a market capitalization greater than $120 billion. Reses joined the company in 2015, shortly before its IPO, and served in various executive roles, most notably as the head of Square Capital, the company’s small business loan division. She left Square in October 2020; Reses had no comment on her fortune.

Born and raised in Atlantic City, New Jersey, Reses attributes her interest in small business to her first job working behind the counter at her father’s pharmacy. She graduated from the University of Pennsylvania’s Wharton School in 1992, and began her career at Goldman Sachs working on mergers and acquisitions. After working her way up to a vice president position at the investment bank, she became CEO of iBuilding, a software company that catered to the real estate sector. After iBuilding was acquired in 2001, Reses left to join private equity firm Apax Partners, where spent more than a decade, becoming a partner and leading the U.S. media team. In 2012, she joined Yahoo, where she led various functions, including human resources and mergers and acquisitions, and served as chief development officer.

Reses took the helm at Square Capital one year after its 2014 formation. Under her leadership, it facilitated some $850 million in Paycheck Protection Program loans to 80,000 businesses during the Covid-19 pandemic, and billions of dollars more in non-federal loans. At Square, Reses also served as the human resources lead and was executive chairman for Square Financial Services, a new bank which became FDIC-insured earlier this year.

Square does not disclose the financial metrics of Square Capital specifically, but the division is a portion of its “Seller” segment, the company’s software and hardware components that cater to businesses. Its Seller division, which generated $1.5 billion of the company’s $2.7 billion in gross profits last year, is Square’s core entity, though recent diversifications in offerings—including the rapid growth of mobile banking service Cash App (which Square created) and the music streaming provider Tidal (which it acquired)—have further helped boost the company’s stock. Another possible area of growth: CEO Jack Dorsey doubled down on his bitcoin bets last month when he announced via Twitter that Square would create a new business dedicated to the cryptocurrency.

Today, Reses is an active fintech angel investor through her family office, Post House Capital, and serves on the board of notable industry players including digital bank Nubank and buy-now-pay-later company Affirm. Last week, she joined the board of directors for newly public entertainment powerhouse Endeavor Group Holdings, the parent company of talent agency William Morris Endeavor, the Ultimate Fighting Championship and the Miss Universe Competition. Reses is part of a group of investors that acquired dating app Grindr last year. She is also an avid art collector with a portfolio that includes pieces by Henri Matisse, Pablo Picasso and Jean-Michel Basquiat.