S 01 Ep 13 | Navigating Markets and Relationships for Growth Steve King has been a CEO five times , pioneered cloud - based enterprise software before the infrastructure existed to support it , and led DocuSign from an unproven category to a company with roughly 70 percent market share . This episode feels less like a formal interview and more like the kind of conversation you would want to overhear . The stories alone are worth the listen . Building Zantaz into the go - to email archiving platform for Wall Street before AWS existed , which meant speccing and building their own hardware and data centers . Joining DocuSign in 2009 when e - signature still had no Gartner research behind it and making the counterintuitive call to pull back from Enterprise and double down on mid - market , where the product had real momentum and lower acquisition costs . However , the deeper thread running through the episode is about how to make decisions under uncertainty . Steve ' s approach is disciplined : set a three - year vision with your team , back it into quarterly and monthly actions , then revisit it every six months with new data . Not as a planning exercise but as a way to give yourself permission to course - correct without losing confidence in the direction .