From Art to Science: How Lightyear Cracked Enterprise GTM After a Costly SMB Detour

Most B2B founders face a critical choice early in their journey: target SMBs or enterprises? In a recent Category Visionaries episode, Lightyear CEO Dennis Thankachan shared how making the wrong choice initially – and then pivoting – shaped their entire go-to-market evolution.

The pivot came after a painful realization about their SMB-focused strategy. "Initially went after SMB, and I actually think that was a bad decision in retrospect," Dennis explains. The core issue? Market dynamics they hadn't fully appreciated: "Enterprises spend way more money on telecom and they also have way more people allocated to the problem. As a result, a product can drive more surface area of value within an enterprise."

This insight catalyzed a complete GTM transformation. They had to rebuild their entire approach, moving from an SMB-focused product-led growth motion to an enterprise sales engine. The transition wasn't just about changing their target customer – it required fundamentally rethinking how they acquired and served customers.

Their initial go-to-market relied heavily on inbound marketing, targeting long-tail keywords that indicated purchase intent. Dennis explains their early strategy: "We identified long tail keywords within Google search that correlate to purchasing intent with a high degree of specificity... Not a ton of traffic on that keyword, but it's likely that a large percentage of the traffic around that keyword is a person that is a buyer."

While this approach still drives valuable leads today, they discovered its limitations. "We still have a wonderful inbound funnel, but there are caps on how far that'll scale," Dennis notes. The enterprise pivot demanded building "something that looks more like the way that a ServiceNow would go to market" – including outbound sales, conferences, and a more traditional enterprise sales motion.

The evolution mirrors what Dennis calls the transition "from art to science" in enterprise GTM. "Early on there is this art period of really determining what the buyer wants, how to price, how to message it, who I should go after," he explains. "And there's a lot of feelings involved and a lot of qualitative determinations of what to go after before you really isolate on something that works and put business model and unit economics around that."

Today, with 275+ customers managing "deep into the tens of millions of dollars of telecom spend," the focus has shifted to optimization. Dennis describes their current challenge as "transitioning from a period of art to science in the context of like an enterprise oriented go to market." This means building repeatable processes around everything from sales quotas to pipeline generation.

The transformation is working. The company has grown 30x in just two and a half years. But perhaps counterintuitively, Dennis attributes much of their recent acceleration to deliberately constraining themselves: "We're now growing faster at bigger numbers with the constraints in place, because we're operating as if that next dollar is not necessarily guaranteed."

This disciplined approach extends to their market focus. Despite pressure to expand beyond telecom, Dennis remains steadfast: "The market is so large, there can feel pressure to like, oh, focus on something outside of telecom, do this, that and the other. I'm very much focused on depth over breadth."

The story offers a valuable lesson for B2B founders: Sometimes the path to faster growth requires making hard choices about what not to do. For Lightyear, that meant abandoning their initial SMB focus, rebuilding their GTM from scratch, and maintaining strict discipline even as they scale. The result is a focused enterprise software company growing at venture scale by solving a specific, painful problem for large customers.