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.

Spreading efforts across startups, SMBs, and enterprises created confusing signals. A deep dive into metrics revealed enterprises, despite being a smaller revenue portion, showed the highest expansion potential, prompting a decisive focus that unlocked growth.

Startups often fail to displace incumbents because they become successful 'point solutions' and get acquired. The harder path to a much larger outcome is to build the entire integrated stack from the start, but initially serve a simpler, down-market customer segment before moving up.

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.

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.

To drive enterprise adoption, Jeeves markets its stablecoin rails not as crypto, but as "Jeeves Instant Pay." This strategy abstracts away the complex technology and focuses on the business outcome CFOs care about: speed, trust, and reliability, using the established brand to underwrite the new technology.

Contrary to conventional GTM strategy, Harvey intentionally targeted the largest law firms first. The rationale was that solving their complex needs and brutal compliance requirements would forge a product robust enough to serve the entire market, creating a powerful competitive moat from day one.

Vertical integration is a direct path to higher profitability in fintech. By obtaining its own licenses and owning the infrastructure stack, Jeeves moved off partners and expanded its gross margin from 40% to over 80%. This captures the entire value chain instead of paying it out to third parties.

Jumping to enterprise sales too early is a common founder mistake. Start in the mid-market where accounts have fewer demands. This allows you to perfect the product, build referenceable customers, and learn what's truly needed to win larger, more complex deals later on.