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Business Day |​​NYT Now

Zenefits’ Leader Is Rattling an Industry, So Why Is He Stressed Out?

By FARHAD MANJOOSEPT. 20, 2014

Inside
    Photo Parker Conrad is the founder of Zenefits, a fast-growing company that is remaking how small businesses buy health insurance and handle other employee benefits. Credit Jim Wilson/The New York Times Continue reading the main story Continue reading the main story Continue reading the main story Share This Page Continue reading the main story Continue reading the main story

    Parker Conrad’s start-up, Zenefits, is thought to be one of the fastest-growing companies in recent Silicon Valley history, and his investors and associates describe him as an uncommonly talented software visionary. But lately, Mr. Conrad often finds himself petrified, his days a series of white-knuckled attempts to escape the clutches of sudden, inadvertent failure.

    “We’re obviously growing very quickly, but I can tell you that that is just as scary as the other way around,” Mr. Conrad said during a recent interview at the company’s headquarters in San Francisco, a space so crowded with newly hired staff members that it was hard to find a room in which to chat. “It doesn’t feel like we’re successful,” he said. “It feels like we’re bouncing from one terrifying near-catastrophe to the next.”

    Open self-doubt is an unusual posture for a start-up executive. Tech founders are, as a class, known to be drunk on their own hype. But Mr. Conrad doesn’t quite fit the stereotype of the young, hyperconfident brogrammer now reported to be running, and ruining, the tech industry. Though he looks the part — he has a boyish face and favors casual, gamer-guy attire — he is, at 34, relatively old. And while the tech press is consumed by apps like Uber and Airbnb, companies that wear their regulation-smashing, world-changing zeal on their sleeves, Zenefits is unusual in that makes software designed to help small businesses comply with regulations rather than fight them.

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