Recruiting
Like raising money, recruiting a great CEO is a chicken and egg problem. Investors often don’t want to invest in an opportunity until there’s proven traction. Yet it’s often difficult to get traction without investment.
Similarly, CEO’s often don’t want to join a company until there’s proof that the company is scaling and the sales model is repeatable. Yet a great CEO is required to scale.
So what does a startup do if it has early-market traction and a great market opportunity, but has not yet proven an ability to scale through a repeatable customer or user acquisition process?

Focus on investors and executives that both recognize the risk and are willing to take it. As one CEO candidate said, “if there were no risk, you wouldn’t need me.”
Spend time with executives who believe they personally can make a difference. Executives who understand the opportunity and the risk, have a vision for the company’s future, and believe that, with their involvement, the company will be that much better off.
When it comes to attracting executives, some amount of selling is required. But if too much selling is required, that’s often a sign that the candidate and the opportunity may simply not be a match for each other.
Sell the candidate into the opportunity, rather than letting he or she self-select out, and there’s increased risk that candidate won’t stick. Those candidates who have a vision for the company and can articulate where they will add value are the ones most likely to be a great match.
Should You Recruit a CEO at All?
Arguably, having to recruit a CEO at all is a problem. Ideally one would only invest in entrepreneurs who can scale as both product visionaries and CEO’s. Bill Gates and Larry Ellison scaled, after all. But Gates had Ballmer and Ellison, at least in the ‘90’s, had Ray Lane.
Scaling all the way from founder to public company CEO is difficult. The skill sets required for founding/early growth and scaling are different, and individuals are often passionate about one but not the other.
Bringing in a CEO is risky. But done right, as in the case of Google, for example, it can really complement technical and product visionaries and free them up to focus on their areas of interest.
Conclusion
Finding an individual with operational excellence, market insight, and product vision combined with a tornado’ing market makes for a great opportunity. If, however, a company is in need of operational excellence to capture a market opportunity fully, the best bet is to find someone who believes in the opportunity — and in himself.
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