How David Duffield Took 20 Years And Four Startups To Develop The Corporate Culture Behind His Enterprise Software Empire

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How David Duffield Took 20 Years And Four Startups To Develop The Corporate Culture Behind His Enterprise Software Empire
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Tony Avelar/BLOOMBERG NEWS David Duffield, chairman of enterprise tech giant Workday, is the 14th-richest man in U.S. tech—a sector where disruption is a religion and startups are patron saints.

But after five-plus decades working in technology, Duffield’s not afraid to challenge this orthodoxy. His advice: Young techies would do better if they learned from the establishment and started their careers at a large, respected company.

“IBM was the company that had the best foundation of core values and beliefs,” Duffield says. “I felt it, but I didn’t understand it.” Duffield explained that it took him over 20 years, during which time he started four companies, to finally apply what worked at IBM to his own businesses. This realization would pave the way for the his two biggest successes, enterprise software firms PeopleSoft and Workday.

His second company offered a similar product but was more successful. Duffield says Integral became the number one vendor of human resources systems in higher education and netted him his first seven-figure fortune, when he sold some of his own stock in the company for $3 million to an investor.

Yet Duffield was anxious about another cultural collapse. “We were Wall Street darlings, things were going well,” Duffield says. “I always had in the back of my mind, when is bureaucracy going to set in here? When are we going to start fighting each other?” On the list of PeopleSoft’s core values: integrity, fun, profitability and critically, making sure employee happiness was a priority, which Duffield says was also critical to culture at IBM.

Some employees were skeptical of Oracle alum Conway’s suit-and-tie approach, which clashed with Duffield’s casual Friday culture, Swasey says. Sandeep Sood, who joined PeopleSoft as a consultant fresh out of college, said workers felt the growing pains. “When I first joined, there were jam sessions where the founders were playing instruments. I could email Dave and he would respond within a day,” he says.

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