Yes you can win in many cases by remaining “hidden” as CEO — but the more enterprise your customer base is, the more important getting and being out there is.

Let’s contrast Box and Dropbox. Both grew into huge wins and highly successful public companies. But Box became 95%+ enterprise by revenue over time, and Dropbox is still 95% SMB and smaller and consumer.

As Box went/tilted from a consumer to an enterprise app, Aaron Levie became highly visible. He stopped sitting in front of a computer all day with the dev team, and put on suits, and spoke everywhere. Box starting putting on 2 big customer events a year, and Aaron started guest blogging on TechCrunch, and just started to be … everywhere. His incredible drive, passion and charisma helped Box break out from the other enterprise solutions in the space. His twitter account became iconic.

Drew Houston, CEO of Dropbox, was much more low profile. Less TV, far fewer events, no big customer conference, etc. Few tweets. He let the product speak for itself, like Facebook, Snap, etc. But — Dropbox is much more of a consumer and SMB focused product.

When the deal sizes are bigger, getting out there and being with customers really works. In person, at events, in the media — it all works. The Box customers I meet love, love, love Aaron Levie. But when you have 100s of millions of users, that stuff helps but the 1-on-1 portion doesn’t really scale. You can’t meet every $5/month customer. But you can meet every $500k a year customer, one way or another.

Look at Marc Benioff. Is he hidden? And they close big, big, big deals.

Either way, “getting out there” helps a lot with recruiting. Unless the product is so popular with end users, the product itself can serve that role.

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