The More Enterprise You Are, the More Visible the CEO Should Be

Many of us founders would secretly like to sit in front of the iMac half the day, and spend the rest of the day planning on making the product even better.  Versus getting on jets, getting on TV, going to events, doing customer steak dinners, etc.

Yes you can win in many cases by remaining “hidden” as CEO — but the more enterprise your customer base is, the more important getting out there 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 twitter account became iconic. His incredible drive, passion and charisma helped Box break out from the other enterprise solutions in the space.

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?  Think about what is takes to close eight figure deals.  He does.

Either way, “getting out there” helps a lot with recruiting no matter how big or small your customer base. Unless the product is so popular with end users, the product itself can serve that role.  In fact, the more enterprise, and the more boring, the product is … the more the CEO is a key part of what makes the product “popular”.  At the end of the day, more of us need to follow the Levie persona path to be successful in SaaS.

Published on April 13, 2018

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