Moderne’s First Enterprise Deal: A 12-Month Journey to Building Customer Trust

When you’re asking companies to hand over their source code, trust isn’t just important – it’s everything. In a recent Category Visionaries episode, Jonathan Schneider revealed why it took Moderne over a year to land their first enterprise customer.

“This is an enterprise product. When we’re dealing with source code, we’re asking basically a customer to give us either in whole or in part their intellectual property,” Jonathan explains. This fundamental trust requirement shaped their entire go-to-market approach.

The breakthrough came through relationships built during Jonathan’s time at VMware. But what happened next surprised even the Moderne team. “When we met them, they had a deck internally of the product that they wanted. And they had pitched this deck a couple times to companies that seemed like they were adjacent to the space. And so we came ready to pitch our product and they pitched us their deck instead.”

This moment highlighted a crucial lesson in enterprise sales: sometimes the best prospects are the ones already trying to solve the problem you’re addressing. The alignment was so perfect that the potential customer had forgotten to update their pitch deck: “When they pitched us that deck, they had forgotten to replace the name of the previous Founder they had pitched it to in a couple places. And so I was looking for my name. It seems somebody else’s name on this deck. Hilarious.”

The year-long sales cycle wasn’t just about technical validation. Moderne invested heavily in building credibility, including $60,000 in brand development before securing funding. As Jonathan notes, “If you’re thinking from the beginning, you want this to be a lasting brand… establishing that identity early is really important because it takes a while for you to fit.”

Their messaging evolved during this period from technical capabilities to business outcomes. Rather than focusing solely on developer productivity, they introduced the concept of “tech stack liquidity” – helping companies move off legacy systems and consolidate vendors. This reframing helped connect their technical solution to strategic business priorities.

Key lessons from Moderne’s first enterprise deal:

1. Technical excellence isn’t enough – trust and security come first
2. Strong references can accelerate credibility building
3. Sometimes prospects have already defined the solution they need
4. Investment in brand and messaging supports trust building
5. Business outcome alignment matters more than technical features

The experience shaped Moderne’s entire approach to enterprise sales. Instead of pushing for quick wins, they focused on building lasting relationships. This patience has paid off in their vision for the future: “If we can mass fix the open source ecosystem upon which we rely, and we can mass fix the applications that depend on them, I think we can solve the technical engineering problems that confront our society more quickly.”

For founders selling to enterprises, particularly those handling sensitive assets like source code, Moderne’s journey offers a crucial reminder: the first deal isn’t just about closing a sale – it’s about establishing a foundation of trust that can support long-term growth.