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Building Amazing Teams

Keith Rabois joined Square as its COO, and has gone on to hold executive roles at PayPal, LinkedIn and Slide. Now part of Khosla Ventures, he sits down to discuss hiring great executives, from recruiting in a competitive ecosystem to the benefits of a risky hire.

DataFox provides summaries of every single panel at SaaStr 2016, all published within a day of the panel itself. If you miss the tactical theater or strategy stage, are networking on the ground, or didn’t get a chance to attend this great conference, we’ve got you covered.

View all SaaStr 2016 panel summaries

Special thanks to Jason Lemkin of SaaStr for putting on this conference and giving us the chance to publish these summaries.

In a nutshell:

  • Hire someone with complementary interests and skill sets.
  • As your company grows, new hires will have a disproportionate influence on culture. Therefore, you must be very careful in hiring.
  • High-growth companies should go for high-upside hires.

Q: When should a founder get a wingman?

A: He came into Square as its COO. Different rules apply, though, and no timeline fits every company.

“If you look at your calendar on Sunday night as CEO and more than half your week is already booked, you’re overconsumed.”

Q: What should you look for in new hires?

A: Think of the offered title as a way of recruiting someone you can’t easily get into your company. Hire for someone with complementary skills and interests – if the CEO hates performance reviews, find a COO who loves them. Not likes; loves.

Q: How do you recruit in this competitive environment?

A: You can’t go after proven talent when you work in a startup. It’s just too hard of a sell. Instead, you have to get really good at identifying high-upside, untested talent. For example, if you’re looking for a VP of engineering, look for someone who displays managerial as well as technical skill, can recruit, and thinks strategically.

Q: How do you grow from 50 employees to 200?

A: For any position you’ve never hired before, meet so many people that you can’t learn anything more about that role.

“Hire managers. Not managers of managers.”

Q: How does culture play in?

A: Consider the ratio of new hires to current employees. As that ratio rises, new hires will influence culture more than be influenced. As a result, you have to be very careful about culture fits.

Q: How far should you promote people in recruiting?

A: If you hire a current VP of finance as a CFO, they might not have enough time to learn how to be a good CFO before they’ll be judged on their results. Have at least some of that conversation upfront, but tell them that they’ll have the chance to prove you wrong.

Q: Should you go for safe or risky hires?

A: If you’re a high-growth company, err on the side of risky hires who have higher upside.

Check out all of our SaaStr panel summaries here, follow us on Twitter at @datafoxco to see live tweets of the event, and visit SaaStr itself for more great content.