&Open’s Enterprise Sales Playbook: How They Won Airbnb as Their First Customer

Most enterprise sales stories start with cold outreach or network introductions. &Open’s began by becoming an Airbnb host. In a recent episode of Category Visionaries, CEO Jonathan Legge shared how they turned this unique vantage point into their first major enterprise win.

Finding the Opening

The opportunity emerged from a failed gift delivery. “We experienced their gifting firsthand. They tried to gift a guest of ours. We saw how generous they were trying to be with their gifting, but we also just saw how epically wrong it went,” Jonathan explains. “Nobody knew they were sending a gift. In particular, the guest, who was the intended recipient, had no idea they were going to get a gift. And then they also had no idea that they’d even tried to gift. And Airbnb had no idea that the gift had failed.”

Making the First Move

Armed with this insight, they reached out to Airbnb. The initial response was dismissive: “We really appreciate that, but you guys are way too small. You’re operating out of your garden shed. We’re gifting across the globe and there’s no way you could help us do this better.”

But persistence paid off. A coffee meeting with visiting Airbnb executives led to an unexpected opportunity: “We’re running an RFP out of San Francisco. There’s eleven US retailers pitching to be our global gifting partners. We’re very curious to hear what you guys have to say. You are definitely the wild cards. You’re the only european company pitching.”

The Six-Month Process

The terms were clear: “If you’re willing to commit to a six month process, we’re willing to listen to you for the next six months and after that we’ll tell you how you got on.” Rather than see this as a disadvantage, &Open used the time to completely reimagine their approach.

“We pitched like crazy and reimagined our e-commerce business and rethought the infrastructure, kind of tried to connect the dots in a different way,” Jonathan recalls. Their approach focused on solving the fundamental problems they’d witnessed as hosts.

Turning Disadvantages into Differentiators

Being based in Ireland meant they had to solve international gifting challenges that US competitors hadn’t faced. “Within reason, it’s relatively straightforward to do gifting across North America,” Jonathan explains. “But when you start to do it across Europe, across APAC, cross border, just taxes, duties, everything else kind of starts to blow up in your face.”

This experience became a key differentiator in their pitch. They understood the complexities of global gifting not from theory, but from practice.

Scaling After Success

Winning the contract was just the beginning. “Went from sending a few hundred gifts out the door every month with our small ecommerce business to sending out 3000 gifts a week within the period of six months,” Jonathan shares. This rapid scaling proved their ability to deliver on their promises.

For B2B founders pursuing enterprise clients, &Open’s approach offers several key lessons:

1. Deep customer understanding can trump industry experience
2. A longer sales cycle can be an advantage if used strategically
3. Perceived weaknesses can become differentiators when properly positioned
4. First-hand experience with the problem creates unique credibility

The result wasn’t just winning a contract – it was building the foundation for a global platform that now serves major brands like Spotify, Atlassian, and Etsy. Sometimes, the best way to win an enterprise deal isn’t to act like an enterprise company, but to leverage the unique insights that only a smaller, more focused team can provide.