Summer’s Remote-First Sales Strategy: Why Their CEO Still Flies Cross-Country for Dinner Meetings

In an era where most startup founders default to Zoom calls, Summer’s CEO Will Sealy recently rerouted a cross-country trip to have dinner with a potential hire in Atlanta. This wasn’t a random decision – it was part of a deliberate strategy that’s helped Summer build relationships with major financial institutions and secure top talent in a competitive market.

The Power of Face-to-Face in a Digital World

While Summer operates as a remote-first company, Will maintains a strong belief in the power of in-person meetings. As he explains in a recent episode of Category Visionaries: “I never forget the value of an in person face to face and showing the other party whether that be someone you’re recruiting, a client you’re trying to win over, or investor of actually making the effort to show up face to face and just how powerful that can be.”

When to Go In-Person

Will recently demonstrated this approach when hiring for key positions: “I took each one of them out to dinner and had a proper conversation with them about the business, why I’m passionate about it, where we’re heading, why I see them as valuable parts of our future growth.” For one crucial hire, he went even further: “I even rerouted a trip back from California to New York and went to his hometown in Atlanta.”

The Post-COVID Advantage

This commitment to in-person meetings has become even more valuable in the post-pandemic environment. Will notes: “I think it’s harder to get people in front of you now than it used to be, but when you have them, there’s almost a novelty to it where they’re like, wow, this is my first in person meeting in a week.”

Balancing Remote and In-Person

Summer’s approach isn’t about abandoning remote work. Will emphasizes: “Summer is a remote company. We do have flexible Co working spaces where people can kind of come to whichever offices in their community if they need it.” The key is knowing when face-to-face interaction can make a crucial difference.

Breaking Through Barriers

This selective use of in-person meetings serves a strategic purpose. As Will explains: “When you’re an entrepreneur, you’re constantly trying to defy the odds. The odds are against you in every direction… So how do you break through walls? How do you do that? And you got to find just basic things that work.”

The Early Lesson

Will’s appreciation for face-to-face meetings stems from early experiences raising capital. He recalls a crucial negotiation where an in-person meeting made all the difference: “He begrudgingly said yes. I think I’m romanticizing how that was. I think I was the one pushing for the in person and I got the opportunity to meet with him face to face.”

The Results

The strategy has paid off. All three recent candidates chose Summer over other offers after their dinner meetings. For founders building remote-first companies, this suggests that strategic use of in-person meetings can be a powerful differentiator.

Will’s approach offers a nuanced perspective on remote work: embrace the efficiency of digital communication, but recognize when personal connection can create breakthrough moments. As he puts it: “That does not mean that I endorse like, we should all go back to the office. But I do think that when you’re an entrepreneur, you’re constantly trying to defy the odds.”

In a world where most interactions have moved online, the strategic use of in-person meetings might be the edge that helps founders overcome those odds.