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As DataRobot Struggled, Executives Sold Private Shares at Peak Valuation

From left, DataRobot executives Tom Levey, Dan Wright (CEO) and Damon Fletcher (CFO). Art by Mike Sullivan
From left, DataRobot executives Tom Levey, Dan Wright (CEO) and Damon Fletcher (CFO). Art by Mike Sullivan
June 15, 2022 6:00 AM PDT

Last year, five top executives at artificial intelligence software startup DataRobot collectively sold $32 million worth of shares to investors, according to confidential documents outlining the sales. The sales occurred after the company was privately valued at $6.3 billion in a funding round. The other 1,200 or so employees, some of whom had worked at the Boston-based company for close to a decade, didn’t get the same opportunity to sell their shares.

The sales were unusual. None of the senior executives who sold shares, including CEO Dan Wright, were founders. In fact, the executives had worked at DataRobot for a year and a half or less when the sales took place. And under their watch, expenses skyrocketed while revenue growth slowed, with the company missing one of Wright’s 2021 revenue targets by 75%.

Based on its financial performance in the fiscal quarter that ended in April, if DataRobot shares were trading at the same valuation multiple as comparable public companies like Palantir and C3 AI, it would be valued at less than $1 billion.

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