DocuSign is a unicorn, a startup worth over $1 billion. To be precise, the early 2000's era authentication startup is worth about $3 billion. According to anonymous inside sources, Rick Osterloh, Google's current Senior VP of Hardware and former CEO of Motorola, had a chance to be the man at the helm, almost took it, then dropped it at the last minute to head back to Google. Having been with Motorola for a long time, he was its CEO when it was sold to Google. When March of 2016 rolled around and a Motorola under Lenovo's banner was reorganizing, Osterloh decided to make his exit. It was during this short time that he was found by a recruiting agency at the behest of DocuSign CEO Keith Krach. Just as everything was set to be made official, however, Google made their offer to Osterloh and the rest was history.
While DocuSign, around in some form since the early 2000's, did manage to attain unicorn status, that doesn't mean much on its own. Under Keith Krach since 2011, the firm focused on fundraising, preparing for a big push in development. With new investors, however, came more expectations. They wanted to see their money come back to them somehow, and Krach didn't want to drum up more funding and essentially rob Peter to pay Paul. Investors at that point pressured him to either announce the company's IPO and begin selling shares, or sell the company off. Not liking either course of action, Krach decided to get out of dodge instead. These circumstances at the time of the would-be change meant that Osterloh ducking out left Krach with no choice but to stay at his post until a replacement could be found, a search that has thus far taken nine months despite the involvement of an outside recruiting firm summoned into the fray by DocuSign's investors.
With Osterloh out of the picture and four of DocuSign's nine top execs disappearing in the chaos, the position seems most likely to go to DocuSign board member and former Symantec CEO Enrique Salem. A final decision has, obviously, not quite been reached at this point. Salem's track record is admirable, but Krach is looking for somebody he's certain will be able to either go through with the investors' suggested options or lead the company to profitability in short order. Insider information points to a decision coming at some point in July. Osterloh, meanwhile, had nothing to say to media outlets about this discovery, nor did anybody else involved. Presumably, he hasn't been quite moved enough by Krach's plight to be convinced to abandon his position at Google, where he heads up Android One and other hardware-centric projects. With top execs gone, an embattled CEO stuck in place and the proverbial bubble about to burst, about the only certain thing about DocuSign's future at this point is that Osterloh won't have much to do with it.