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DocuSign CEO Preps for an IPO, While Trying to Appease His 11 Bosses

Insiders at the $3 billion startup blame a series of missed deals and a blundered CEO search on an oversized, indecisive board.

CEO Tangle

Illustration: Leon Sadler for Bloomberg

Dan Springer inherited a lot when he became chief executive officer at DocuSign Inc. this year. The company’s electronic document software is an essential part of the real estate and insurance industries in the U.S. Investors value the business at $3 billion, making DocuSign one of America’s most valuable technology startups.

It’s also one of the oldest. Numerous suitors have come and gone since DocuSign was founded in 2003, including recent overtures from IBM, Microsoft Corp. and Oracle Corp. The San Francisco company has been discussing plans for an initial public offering since at least 2013 but remains private. Even Springer’s hiring took longer than usual. He was appointed in January after a CEO search that lasted 15 months, more than three times longer than the norm.