I just wrapped up my 78th customer call since stepping back into the Flexport CEO role 6 weeks ago. I’m a fan of business in the same the way some people are fans of sports. That means I have the greatest job in the world, getting a backstage pass to see how these awesome…
— Ryan Petersen (@typesfast) October 20, 2023
At our first big digital event, SaaStr Summit: Bridging the Gap, Stewart Butterfield, CEO of Slack, shared a funny story. He said with work-from-home, he was able to talk to a lot more customers. A lot more. And that he was Zooming with a smaller enterprise customer they’d just closed, who told him “She was worried about Slack.”
“Why are you worried about the company?” Stewart asked.
“Because the CEO has time to talk to me! That’s always a bad sign!”
Ok, laugh. But there’s a bunch of interesting points in that story. Stewart had more time to talk to more customers — and go further down the list and talk to customers he didn’t have time to before.
One thing I’ve learned over 15+ years of selling in SaaS is that I truly have never lost a customer I’ve ever visited in person. And I rarely lost a customer talked I to “in person” over a lengthy Zoom or two.
In other words, I almost never lost a customer that as CEO I had a personal connection to.
Customers love to talk to the CEO. Especially if the CEO listens to their concerns. They feel respected. They feel heard. They feel a bond. A bond that lasts years.
And it turns out, it even works in a 5 person company. Maybe even just as well.
"Why every founder can at least be decent at sales:
Customers want to talk to an expert. Subject matter experts that will solve their problems.
And that you can do well as a founder." pic.twitter.com/7cbObYZi3S
— Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk) March 19, 2025
Your customers have invested a lot in your product. It means a lot to them to talk to the CEO, even when the vendor is tiny. It may even mean more. So don’t wait until you are a bigger start-up to start talking to more customers. Leverage the fact that the title “CEO” matters to customers, no matter how new and raw your startup is.
Leverage that. It’s a retention and upsell weapon. Customers love to talk to the CEO.
So do 2x more customer meetings than you’re doing now. Talk to at least 10 customers a week over Zoom. 20 if you can make it happen. Go visit 5-10 a month, one way or another. They’ll trust you more. Stay longer. And buy more.
