Josh Stein on management practices
From Josh Stein of DFJ: What Makes a Great SaaS CEO · · SaaStr
“I can sit down and teach anybody how to do a one-on-one review — it's not that hard, but you have to want to do it; if you're afraid of public speaking, get out there and do it — practice makes perfect.”
On , Josh Stein, Partner at DFJ at Draper Fisher Jurvetson, spoke about management practices during Josh Stein of DFJ: What Makes a Great SaaS CEO on SaaStr.
About Josh Stein
In a 2017 session, Josh Stein, a partner at Draper Fisher Jurvetson (DFJ), discussed the qualities of a great SaaS CEO. He argued that a great CEO makes the company's vision "something that transcends the company and captures the imagination," citing Elon Musk as an example. Stein identified three distinct break points for CEOs, occurring at roughly 40–50, 200, and 1,000 employees, where communication, span of control, and external focus become critical challenges. He also stated that the role of a CEO is to be a "magnet" for talent and capital, and that the "people stuff" — including leadership, processes, and managing career aspirations — often trips founders up. Stein noted that while skills like public speaking or conducting reviews can be learned, the CEO must be committed to "go to school on the side" and learn continuously. In a 2013 interview, Stein described DFJ's approach to early-stage investing, stating that the firm looks for "great people who can sell us and get us hooked on an idea," who are motivated by solving a problem rather than by money. He noted that because it is now cheaper and faster to start a company, he would advise a SaaS founder without at least a minimum viable product or customer conversations to "go do that and come back." Stein commented that product-market fit is a "moving target" and that he is more interested in a founder's "demonstration of skill and competence." He also described AngelList as a complementary tool for deal flow, though he noted DFJ had not used its syndicate model.