From Skepticism to Sales: How Cinchy Turns ‘You’re Crazy’ Into Customer Conversations

From Skepticism to Sales: How Cinchy Turns ‘You’re Crazy’ Into Customer Conversations

When you’re telling enterprise buyers that one of their fundamental practices is wrong, expect skepticism. In a recent episode of Category Visionaries, Dan DeMers revealed how Cinchy doesn’t just handle skepticism – they actively court it as part of their sales strategy.

Embracing the Crazy For most founders, being called crazy would be concerning. For Cinchy, it’s validation. “Quite frankly, a lot of people think you’re crazy, especially in the early days,” Dan explains. “If you’re truly creating a category, or at least you believe you are and no one thinks you’re crazy, then there’s something wrong with that.”

The Sleep Analogy To illustrate the challenge of selling a radically new concept, Dan uses a powerful analogy: “Imagine if you discovered that sleeping is actually evil. It’s actually a byproduct that you’re, I don’t know, lacking a particular vitamin or something, and you’ve discovered this and you have the cure for sleeping and try selling that to the world.”

The parallel to Cinchy’s challenge is clear. They’re telling organizations that data integration – a practice as fundamental as sleep – is actually harmful. “Today, integration is perceived as good, but that doesn’t mean that can’t be changed,” Dan notes.

Converting Skepticism into Curiosity Rather than trying to minimize skepticism, Cinchy leans into it with provocative messaging. At a recent Gartner event, their “no integration” messaging drew significant attention. “At least a third of the traffic that came to our booth and were definitely one of the busiest booths at the event was, what does this mean? The obsolescence of integration? Tell me more,” Dan shares.

The Education-First Approach To bridge the gap between skepticism and understanding, Cinchy invested heavily in educational content. “When we started to get inbound prospects… they would hit our site and they would go to Cinchy TV and they would talk about how they would watch literally hundreds of hours of the content,” Dan recalls.

This self-education process transforms skeptical prospects into informed buyers. As Dan explains, “The best lead that we could ever get is one that stumbled upon us, went to our site, watched an initial video, and then many hours of content watching later, they reached out to us and they’re already educated, they already know the story.”

The Different vs. Better Framework Cinchy’s approach to handling skepticism is rooted in their “different vs. better” framework. “Different, not better, is amazing at getting attention, but it doesn’t translate to immediate sales,” Dan explains. The solution? “We are different, not better is the hook. But when it comes to a sales process, we are actually better because we are different.”

Building Category Infrastructure To help overcome systemic skepticism, Cinchy created the Data Collaboration Alliance. “Rather than Cinchy Inc. pushing for standards, it’s going through the alliance, where we’re working with other organizations and data privacy experts… it creates a lot less friction and anyone can join,” Dan explains.

The Historical Perspective Dan puts their challenge in historical context: “You can see ads from the not too distant past, the more doctors than any other smoke Camels, right? Like smoking was prescribed. It was good for you. What’s good for you today is often learned later that it is not good for you.”

Lessons for Category Creators Cinchy’s approach to handling skepticism offers valuable lessons for founders:

1. Use skepticism as validation for category creation
2. Convert skepticism to curiosity through provocative messaging
3. Enable self-education through comprehensive content
4. Build ecosystem infrastructure to reduce friction
5. Frame resistance in historical context

For B2B founders facing market skepticism, Cinchy’s experience suggests that the goal isn’t to eliminate doubt – it’s to harness it. By creating the right conditions for self-discovery and education, you can transform “you’re crazy” into “tell me more.”

The key is understanding that significant skepticism isn’t just normal for category creators – it’s necessary. If everyone immediately agrees with your vision, you might not be pushing hard enough to create something truly transformative.