Square Loses Another Exec to Venture Capital

Photograph by Jin Lee/Bloomberg

Venture capital firms are swiping executives away from Square, the hot mobile-payments startup.

For the second time in nine days, a high-ranking executive at the payments startup Square has landed in venture capital.

This time, it’s Jared Fliesler, who served as a vice president of user acquisition and business operations at Square, the San Francisco-based company that makes a credit-card reader for phones and tablets. Fliesler is joining Matrix Partners in Palo Alto, California, where he’ll be looking to invest in early-stage Web and mobile companies.

The announcement follows the high-profile departure of Keith Rabois, who resigned as chief operating officer of Square in January after allegations of an improper relationship with another employee. “I did not do the horrendous things I am told I may be accused of,” Rabois wrote on his blog. Last week, Rabois joined Khosla Ventures as a partner, and tweeted, “Any bold, ambitious entrepreneurs around?”

At 28, Fliesler is younger than many of the entrepreneurs he likely will end up advising, but he boasts an impressive list of accomplishments. Prior to joining Square, Fliesler was an exec at Slide, and helped negotiate the company’s $200 million sale to Google in 2010. He stayed at Google for a year before taking a job at Square when the startup had about 150 employees. Now, it’s over 500.

Fliesler said he wasn’t looking to leave Square, but jumped at the opportunity to work with very young companies seeking his expertise. Matrix has a reputation of being an active investor, he said, unlike some other firms that just cut the check and get out of the way.

“I had no desire to get into something that was hands off and passive,” Fliesler said. “In this role, I can work with a bunch of companies in that phase that I absolutely love.”

Matrix’s well-known investments in recent years include online retailers Gilt Groupe and JustFab, question-and-answer site Quora, and customer-service-software maker Zendesk.

The venture firm missed out on investing in Fliesler’s former employer, but Matrix is hoping he can help find the next Square.

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