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Top Yahoo Exec Jackie Reses Heads to Square as Senior Exec (Update)

The brain drain at Yahoo continues for CEO Marissa Mayer.

Andrew H. Walker / Getty

Top Yahoo exec Jackie Reses is joining Square as a senior executive there.

Sources said the announcement could come as soon as tomorrow by the San Francisco payments company, adding that her last day at Yahoo was Friday.

Reses has had deep financial experience before her time at Yahoo — where she has had jobs in a variety of departments, including human resources and M&A. Her most recent title was chief development officer.

Before she joined Yahoo, Reses worked at private equity firm Apax Partners, leading its U.S. media practice, and was at Goldman Sachs in M&A before that. While it’s not clear what her role at Square will be, it will be focused on this area.

One possibility: Head of Square Capital, the company’s cash-advance business, which is growing fast and in need of a leader. The business now doles out $1 million a day to its merchants in lump-sum cash advances, which Square recoups, plus a fee, by taking a percentage of a business’ daily credit card payments.

(Update: Reses will indeed be joining Square to run Square Capital, the company announced Monday morning. “Jackie’s understanding of the financial services industry and her background in tech and investing make her the perfect fit to lead Square Capital, and I’m thrilled she is joining our leadership team,” CEO Jack Dorsey said in a blog post. Square Capital is part of a crucial new business unit that the company is expecting to help differentiate itself from competitors and increase its profit margins.)

Square itself is seeking cash and is in the midst of an IPO, entering a Wall Street arena Reses has much experience with.

While Reses is an interesting hire for Square, the move shines a harsh light on the continuing exodus of executives from Yahoo under CEO Marissa Mayer as her efforts to turn around the Silicon Valley icon have sputtered.

Until recently, Reses was one of Mayer’s closest advisers. But a number of sources around Silicon Valley in recent months noted that she had been expected to leave the company after it spun off its assets from China’s Alibaba Group by the end of the year.

Sources said she had been considering a number of options, and was not expected to head the spinoff company, as had previously been reported.

That transaction is close to being complete, but sources said that the opportunity at Square was too good to wait. Reses will be reporting to Dorsey, who is also the CEO of Twitter.

Reses rounds out a team that Dorsey has been strengthening of late and is now one of several women in top jobs at Square. Others include Sarah Friar as CFO and operations lead; Francoise Brougher as the business lead; and Alyssa Henry, as “seller lead,” in charge of product management, design and engineering for Square’s seller-facing products.

Square declined to comment (and Yahoo never does, so why bother?).

Bloomberg first reported the news earlier tonight. (Well played, Brad Stone, as I have been chasing Jackie’s expected departure for months!)

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