How Monte Carlo Built a Customer-Obsessed Sales Machine: From Cold Calls to Category Creation

How Monte Carlo Built a Customer-Obsessed Sales Machine: From Cold Calls to Category Creation

The most successful startups often begin with founders doing the unglamorous work of cold calling potential customers. In a recent episode of Category Visionaries, Monte Carlo CEO Barr Moses revealed how these early customer conversations laid the foundation for both their sales organization and their category.

Starting with Cold Calls

When validating Monte Carlo’s initial concept, Barr took an unusually methodical approach. “I actually worked on a couple of different ideas and kind of tested out different ideas in parallel. And the idea was to see which idea has traction,” she explains. Her methodology was direct: “I would literally cold call people and say like, hey, do you have this issue? Hey, is this a problem for you?”

Finding the Signal

These cold calls quickly revealed which problems resonated. “The idea of, hey, the data is wrong, what can I do about this? Or why am I always the last person to hear about this? Why am I hearing from downstream consumers that the data is wrong?” These questions consistently struck a nerve, while other ideas fell flat. “Some of the ideas that I worked on were terrible and nobody cared about it. They would just hang up on the phone.”

Building Customer Obsession into Sales DNA

Rather than treating these early customer conversations as just validation exercises, Monte Carlo used them to establish their sales culture. “When we hire people, both folks in management positions or not, we try to understand what motivates them. And if we understand that you care about making an impact by your customers, that is what we look for… we screen for that pretty aggressively,” Barr shares.

The Two-Goal Framework

Monte Carlo developed a simple but powerful framework for their sales organization: “The only thing that matters at Monte Carlo now and forever is getting as many customers as possible and making customers as happy as possible. And every single person at Monte Carlo should be working towards one of those two goals.”

Learning Customer Language

Instead of creating their own sales messaging, Monte Carlo let customer language guide them. “I think oftentimes it’s easy to market or create content with yourself, with your own company in mind… It’s very different to come from that angle versus what is the language that our customers are using? What words do they use to describe their own problem?”

Making Category Creation Everyone’s Job

Unlike companies that separate sales from category creation, Monte Carlo made it a unified effort. “This is 100% a company wide thing,” Barr emphasizes. Each department contributes differently: “Our product team is basically building a product that’s completely innovative… Our marketing team is responsible for spreading or speaking with customers or getting the building the awareness around the fact that there is a solution for this problem.”

The CEO’s Ongoing Role

Even as the company scaled, Barr maintained a heavy schedule of customer interaction: “I probably do between one and three speaking opportunities per week for the last three and a half years or so since we started Monte Carlo.” This ongoing customer contact helps maintain the company’s customer-centric culture.

Results of the Approach

The impact of this customer-obsessed sales approach is evident in customer feedback. As Barr shares, customers frequently say “we love working with you all, and you guys have totally changed the way that we work. You can’t imagine doing our jobs without Monte Carlo.”

For B2B founders building their sales organizations, Monte Carlo’s experience offers several key lessons:

• Use early customer conversations to build sales culture, not just validate ideas
• Let customer language shape your sales messaging
• Make customer impact a key hiring criterion
• Keep founders involved in customer conversations even as you scale
• Align the entire company around sales and customer success

The conventional wisdom suggests separating sales, marketing, and category creation. Monte Carlo’s success suggests that in B2B tech, these functions might be most effective when unified around a singular focus on customer impact.