Dear SaaStr: What Qualities Make a CEO The Best In Their Industry?

I’ve invested in 5 start-ups that had a $1,000,000,000+ cash exit or IPO.

The CEOs were all quite different. Some extroverted, some introverted. Some wicked smart, some merely very smart. Some direct, some warm and friendly.

But what made them great:

  • Ability to attract amazing co-founders and execs. Almost all of them had an amazing CTO or CPO, and hired a simply epic VP or two. Not just great, but epic.
  • Ability to iterate pretty darn quickly. Good but not great CEOs just can’t find a way to iterate fast enough. When the competition does, you get left behind. Not overnight. But eventually.
  • Never, ever, never quitting. Ever. Good but not great CEOs don’t necessarily resign but sometimes they stop being 100% committed. It’s rational when it ends up harder than anyone expected. Which it always does.
  • Seeing white space others can’t quite see. The best CEOs see white space in the market that either others don’t see, or more often, sort of see, but this is too small. I love the session below with Okta’s CEO on how everyone knew the identity space matters, but no one thought it could be that huge as a business. Including Todd’s ex-boss, Marc Benioff.
  • Bulldozing through the tougher times. The tough times really almost kill you. The very best bulldoze through them. Not without scars or pain. But they bulldoze through it.
  • Always going truly long. The very best CEOs really want to do what they are doing for 10–15–20 years. And have a true mission and vision to get there. It sounds trite, but it’s true.

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