Back in 2011, DocuSign replaced its founding CEO, Tom Gonser, with high-profile Silicon Valley veteran Keith Krach. Krach is a well-regarded operator and kicked DocuSign’s business into gear, raising well over $700 million and being valued highly enough to create several unicorns. But Krach, who is chairman and CEO, didn’t want to stay in the role forever and back at the end of 2015, he signaled to staff that he wanted to step back from the CEO role and that the board was aggressively searching for a replacement CEO.
That search, however, was a difficult process. Scuttlebutt suggests that DocuSign was all ready to sign up one candidate, Rick Osterloh, who was poached, at the last minute, by Google’s business unit for all the most ambitious projects, Alphabet. It was pack to the drawing board for DocuSign, which had to balance the uncertainty of the situation with the desire to find the right person.