Closing enterprise deals is not about luck or smooth talking. After decades in Silicon Valley and sixteen years leading a firm that helps companies break into enterprise sales, Jonathan W. Buckley has learned that there is real math behind what works. As principal and owner of The Artesian Network, he has watched more than half of his clients reach an IPO or strategic acquisition. His approach removes the guesswork and focuses on what the data actually reveals about winning in high-stakes B2B sales.
Finding Purpose in Enterprise Sales
Buckley did not simply wake up one day and decide to leave his CMO career behind. Years of working with both public and private companies in Silicon Valley showed him exactly where the system kept breaking down. Early-stage companies often had strong products but could not break into enterprise sales. That gap is what led to the creation of The Artesian Network “About sixteen years ago, I started The Artesian Network to help early-stage companies get their products into enterprise-type sales, all within B2B technology,” he explains. The results speak for themselves. “A little over fifty percent of our clients have ultimately made it to IPO or a strategic acquisition.”
Preparation & Strategy
There is a reason most deals fall apart, and it happens long before anyone meets in person. “It starts with a multi-part process,” Buckley explains. “Preparation and strategy are always of supreme importance, along with very deep research.” You need to know the client’s industry, financials, and competitors. More importantly, you need to understand their priorities. “Really understanding and walking in their shoes is critical,” he says. The numbers show how much effort this takes. Six to seven stakeholders are typically involved in an enterprise sale. There is your main buyer, but several others can either move the deal forward or stop it completely. Each of those people needs five to six meaningful touches before a deal closes. Many salespeople hear that and give up. Buckley sees it as a roadmap.
Pitch Execution
Trust often develops in unexpected ways. Many salespeople believe they need to present a flawless solution, but Buckley takes the opposite approach. “Be really transparent about the risks and limitations to build trust,” he advises. “No one wants to hear an all-sunshine story.” Every partnership comes with challenges. Being upfront about them makes you credible instead of suspicious. He encourages sales teams to show expertise early through strong references and concrete examples of past success. But everything has to tie back to what the client actually needs. “It is about them, not about you,” Buckley says. “Emphasize partnership, not selling.” High-value deals are not one-time transactions; they are collaborations built around something bigger.
This is also where many sales teams go wrong. Leading with ROI or technical features might seem logical, but it rarely works. “You are not selling just on ROI,” Buckley points out. “You are selling a story to start with.” The research supports him. People remember facts up to twenty-two times more effectively when they are presented within a story rather than as isolated data points. Raw statistics are recalled only about five percent of the time, while stories stick roughly sixty-five percent of the time. The impact on revenue is easy to calculate. Imagine one hundred prospects considering a hundred-thousand-dollar solution. Without emotional storytelling, perhaps ten will buy. Add effective stories that build trust, and that number rises to twenty or even twenty-five. “That is an extra one to one and a half million in revenue from the same pipeline,” Buckley explains. The type of story matters too. Buyers want to see how others have solved similar problems. A 2022 B2B Demand Generation Report found that sixty-eight percent of buyers need peer examples before committing to a high-value purchase. Your case studies are not just marketing materials. They are a critical part of the sales process.
Trust & Relationship Building
Creating urgency does not mean using pressure tactics. It means connecting what you are selling to real strategic deadlines or risks the company already faces. “Position the cost of inaction as greater than the investment required,” Buckley explains. Once a buyer understands what they stand to lose by waiting, the timeline often takes care of itself. This is where many deals go off track. Salespeople panic and start offering discounts. That is a mistake. “Negotiate based on ROI and outcomes, not discounts,” Buckley insists. If you have built the story, connected to their metrics, and demonstrated clear value, price should not be the sticking point.
When the meeting ends, the real work begins. Send executive recaps that clearly outline value, next steps, and timelines. AI tools such as Otter or Firefly can now handle most of the note-taking, saving hours of administrative time. Keep sharing insights and relevant updates, but stay coordinated. Marketing emails that do not align with your messaging can easily derail momentum. Buckley also recommends something that surprises many teams. “Introduce your implementation team early to build delivery confidence,” he says. Bring them in before the contract is signed. It shows that you are already thinking about outcomes, not just the close. The entire system works because it reflects what actually happens in real enterprise sales, not what sounds good in a seminar. Sometimes the best strategy is simply paying attention to what the numbers are telling you.
Connect with Jonathan W. Buckley on LinkedIn to learn proven strategies for closing enterprise B2B deals that scale.
