Founder Amanda Kahlow deliberately targeted large enterprise customers first for both her companies. This defies the common advice to start with SMBs. Her rationale: it’s easier to simplify an enterprise-grade product for smaller markets than it is to scale a simple product up.

Instead of the typical land-and-expand model, Templify aimed for company-wide rollouts from the start. This created immense stickiness and gave them an 'unfair advantage' to work from inside the organization, growing revenue by going deeper with specific teams after the initial wide deployment.

Counterintuitively, Filevine discovered that larger customers were easier to work with. They were more sophisticated, had internal resources for implementation, and understood technical limitations. Smaller customers, in contrast, often had "beer money and champagne tastes" with unrealistic expectations.

Despite selling into the regulated trucking industry, Samsara initially avoided large, risk-averse lighthouse accounts. They targeted the mid-market, which required less social proof and offered faster sales cycles. This approach not only generated revenue but also created rapid product feedback loops, accelerating innovation.

Most SaaS startups begin with SMBs for faster sales cycles. Nexla did the opposite, targeting complex enterprise problems from day one. This forced them to build a deeply capable platform that could later be simplified for smaller customers, rather than trying to scale up an SMB solution.

Despite being profitable with 20% EBITDA margins, Sense raised a large Series C. The primary driver wasn't operational cash, but securing a strong partnership with an investor they vetted personally over several dinners. The round also funded expansion and provided employee liquidity through a tender offer, optimizing for relationships over valuation.

By initially focusing on the underserved SMB market, SmithRx built a highly repeatable and scalable platform. The operational rigor developed from handling thousands of smaller clients was the key to later "crossing the chasm" and successfully serving large, demanding enterprise customers.

In industries with long sales cycles like healthcare, early traction isn't about dozens of logos. For YC's Demo Day, Aegis focused on securing just one large medical billing company as a happy, paying customer. Deep engagement—evidenced by data sharing and product co-development—is a powerful early signal for investors.

Sirian validated its market by securing five paid pilot agreements from large manufacturers based on its vision and understanding of customer pain points. This approach proved market demand and de-risked the venture before significant engineering investment, a powerful strategy for enterprise-focused founders.