Building successful sales strategies isn’t rocket science, but most companies get it wrong anyway. They pick whatever seems trendy or copy what worked for someone else, missing the fact that different markets need completely different approaches. Jonathan W. Buckley learned this the hard way during his 15 years helping companies figure out which sales model actually fits their business.
Collecting Market Shifts as Experience
Most consultants talk about frameworks and methodologies. Buckley has a different way of putting it: “Some people collect stamps. I collect market transformations.” It’s an odd way to describe a career, but it makes sense when you look at what he’s done. After working as a CMO for both public and private tech companies in Silicon Valley, he’s now principal consultant at the Artesian Network, helping businesses navigate the mess of scaling up. The numbers tell part of the story. Buckley’s worked with companies that have generated “probably about $3 to $5 billion in client exits in total.” But what’s more interesting is how varied those exits were. Some companies used direct sales, others went through channel partners, and some built product-led growth engines. A few even worked through OEM partnerships where manufacturers embedded their products into bigger offerings.
Understanding Direct Sales Numbers
Selling directly to big companies follows rules that most people don’t know exist. There’s actual math involved, which Buckley learned through years of watching what works and what doesn’t. “When selling to the enterprise in large sales, we have to hit six to seven buying constituents about five to six times before we can trigger an interest that has a statistical probability of going to the outcome we want, which is a sale,” he explains.
That sounds complicated, but it gets worse when you realize each person in that organization cares about different things. The executives want to hear about beating competitors and gaining market advantage. “Vice presidents and above want to hear how this product or service will enhance their strategic foundation in the market, how it helps them stack up against their competitors,” Buckley notes. But talk to a director, and they’re worried about budgets and headcount. “Directors, senior directors, tend to be more influenced by discussion about how it impacts headcount and budgets.” Go down one more level and everything changes again. “Managers, sometimes staff, are more interested in risk and time reduction as a result of employing the product.” So you end up needing different messages for each level, delivered through whatever channels actually reach them.
Channel Partners and the MSP Game
Sometimes selling direct doesn’t make sense, especially when you’re trying to reach mid-market companies. That’s where managed service providers come in. They already have relationships with the customers you want to reach, so you work through them instead of trying to build those relationships yourself. Buckley saw this work with a company called Accent back in 2010. They started with just “16, 17 MSPs representing the product.” Most companies would have been happy with slow, steady growth from there. But Buckley’s team had bigger ideas. “Over the next two years, we brought that number to 2000 MSPs,” he recalls. Accent eventually had a successful exit, partly because they figured out how to scale through partners. The secret wasn’t just recruiting more MSPs. They built “a sales portal with materials that the MSPs or the channel partners could use to reformulate their own specific messaging, positioning, and promotion of the company’s products.” Give partners the tools they need, and they’ll do the selling for you.
Navigating Long OEM Sales Cycles
If you think enterprise sales are slow, try selling to original equipment manufacturers. “You have to plan for up to 18 months in an OEM type model because you’re fitting into their product lifecycle,” Buckley warns. That’s because you’re not just selling a product, you’re asking them to build your technology into their product. The sales process looks similar to enterprise deals in some ways. You still need to convince six to seven people, and you still need to hit them multiple times. But the conversation is different. You’re helping them understand “how your software could enhance the total market value of their end product, their competitive position, and the overall perceived value.”
Driving Growth with Product-Led Models
Product-led growth changes everything about how you think about sales. Instead of having salespeople chase prospects, you build viral elements right into the product. “PLG flips the script, letting your product do the selling, in essence,” Buckley explains. But it only works if you can prove value fast. Really fast. “In 15 minutes or less when selling to businesses, your product needs to show obvious value,” he explains. That rules out anything complex or requiring lots of setup. Slack is the classic example. “The more people join Slack, the larger the network grows. It has a network effect.” Each new user makes the product more valuable for everyone else. When PLG works, “one customer begets another customer, or one user begets another user, and the cycle continues.”
All this experimentation with different sales models has taught Buckley something important about what separates successful companies from the rest. At the Artesian Network, “over 50% of our clients have ultimately reached IPO or an M&A transaction, a positive exit to their business model.” That’s not luck or timing. It comes from picking the right sales approach for each specific situation instead of following whatever’s popular.
Connect with Jonathan W. Buckley on LinkedIn to explore how tailored sales models can transform business outcomes.
