How Crosschq Built Their First 100 Enterprise Deals: A Founder’s Journey from Self-Service to Enterprise Sales
Every B2B founder faces a crucial transition: moving from founder-led sales to building a scalable sales organization. In a recent episode of Category Visionaries, Mike Fitzsimmons shared how Crosschq navigated this evolution, offering valuable insights for founders facing similar challenges.
The Early Days: Every Deal is Personal
“Early on, the go to market was I did the first hundred deals, right? That’s just what you do. You claw, you scrape, you figure it out,” Mike reveals. This hands-on approach wasn’t just about closing deals – it was about understanding the market and refining their message.
The Message Evolution
One of the key lessons from those early deals was the importance of messaging. Initially, Crosschq approached prospects with a confrontational message about their hiring practices. As Mike explains, “We’re way out in front with this whole idea of quality of hire and connecting outcomes and coming into companies with a big bat, telling them that you’re not doing a good job of this, you’re not doing a good job of your hiring.”
This approach quickly proved ineffective. “We realized pretty quickly that’s not the right message to your buyer,” Mike shares. “This buyer is doing the best they can do. They’re doing the best they can do with what they have at their fingertips.”
Building a Scalable Sales Motion
The transition from founder-led sales to a scalable organization brought its own challenges. “Now we look like a more traditional enterprise sales team,” Mike notes. “Sales cycles are longer, right. Sales cycles are six months now instead of one month. As you’re moving up market and moving those larger opportunities.”
This evolution required significant changes in their approach:
- Moving away from quick closes to longer, more strategic sales cycles
- Shifting from digital-first to high-touch engagement
- Developing more sophisticated enablement and processes
- Simplifying the product messaging
The Product-Market Fit Test
The transition from founder-led sales served as a critical test of product-market fit. As Mike explains, “It’s a great litmus test on what kind of product market fit you have. You find yourself wanting to be in as many of those conversations as possible, and your ego probably as much as anything, can’t let go.”
But the real test comes when other people need to sell the product: “If you can’t get someone else to sell it as well as you sold it, then you probably don’t have the fit that you hoped you had.”
The Ongoing Role of the Founder
Interestingly, Mike suggests that founders never completely step away from sales. “I’m not sure that ever actually goes away though, that founder led sales. There’s not a deal happening in our company now that I’m not touching in some capacity if it’s of a certain scale.”
This ongoing involvement serves multiple purposes:
- Maintaining connection with customers
- Supporting strategic deals
- Ensuring messaging consistency
- Providing credibility in important conversations
Lessons for B2B Founders
Crosschq’s journey offers several key insights for founders transitioning from early sales to building a scalable enterprise organization:
- Use early deals to test and refine messaging
- Focus on enablement and process simplification
- Accept longer sales cycles as you move upmarket
- Stay involved in strategic deals even after building a team
The evolution from founder-led sales to a scalable enterprise organization isn’t just about hiring salespeople – it’s about creating a repeatable process that others can execute. As Mike puts it, you need to focus on “the right levels of enablement and the right process and frankly simplifying the product messaging enough where anyone else could sell it.”
For B2B founders, this transition represents a crucial moment in their company’s growth. Success requires not just letting go, but building the infrastructure and processes that allow others to succeed in their place.