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Nicklaus: Software firm's sale completes a hat trick for St. Louis entrepreneur

Nicklaus: Software firm's sale completes a hat trick for St. Louis entrepreneur

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Jim Eberlin just turned an entrepreneurial hat trick.

Wednesday’s sale of TopOpps, his 7-year-old software firm, marked the third time Eberlin has taken a company from startup to successful exit. His secret sauce, he said, is persistence.

“You have to keep at it, keep moving and keep pushing,” he said. “If you keep going, there’s always a move you can make.”

Eberlin made the right moves after founding Host Analytics in 2001; it has grown into a California-based company called Planful. He followed that up in 2011 by starting GainSight, which was worth $1.1 billion when it landed a private equity investment last year.

Xactly, the San Jose, California, company that’s buying TopOpps, didn’t disclose a purchase price. Eberlin said it provided “a good return” for his investors.

Cultivation Capital, a St. Louis venture capital firm, was among them. Cliff Holekamp, a Cultivation managing director, thinks the successful exit will help keep other investors interested in backing other tech startups.

“Exits are always good for everyone,” Holekamp said. “It puts that capital back to work in new opportunities.”

Eberlin’s hat trick is a rare feat. “It makes him the undisputed software-as-a-service king of St. Louis,” Holekamp said. “The odds of doing one tech startup and being successful are very low, and to do it three times in a row is amazing.”

TopOpps’ software uses artificial intelligence to help companies predict the success of their sales efforts. It already had a sales partnership with Xactly, and Xactly Chief Executive Chris Cabrera sat on TopOpps’ board.

“I worked really hard to get them as a customer, and then it made sense for our products to work together,” Eberlin recounted. “Once they got to start selling our product, that was the proof, and eventually it made sense for them to own us.”

Holekamp said Xactly is committed to keeping TopOpps’ 30 employees, including the downtown St. Louis office where most of them work. “If they have a team that’s performing and executing, they don’t want to lose any of them,” he said.

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Eberlin believes his St. Louis employees will benefit from being part of a larger Silicon Valley company. “We need more of the experience they have in the Bay Area,” he said.

Over the last decade, Eberlin has used his own Bay Area connections to help build the startup ecosystem in St. Louis. He volunteers with the annual Arch Grants competition and has mentored some of its winners.

Marc Bernstein, chief executive of artificial intelligence startup Balto Software, worked at TopOpps for a year and a half and met one of his co-founders there.

“The experience was truly transformative,” Bernstein said. “Jim would bring in ideas he had heard about from Silicon Valley, and that meant the company was always trying new things and always on the cutting edge. That was an important lesson.”

Bernstein was excited to learn of TopOpps’ exit, calling it “exactly what St. Louis needs.” Within a few years, he predicted, “I think we’re going to have a TopOpps Mafia” of other firms started by entrepreneurs who worked for Eberlin.

As for Eberlin’s own future, the 57-year-old said he is committed to working for Xactly for now, helping Cabrera build a dominant firm in revenue intelligence software.

Would he ever try to follow up on his hat trick with startup No. 4? “I’m going to take a little time, discuss things with my wife,” he said. “Down the road, who knows what happens?”

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