Faced with a well-funded competitor built on Salesforce, Filevine won by focusing on "fit" and a seamless user experience. While the competitor leveraged Salesforce's features, their product felt "jiggered" to lawyers. Filevine's bespoke platform ultimately achieved an 80-90% win rate in head-to-head deals.

Startup founders often sell visionary upside, but the majority of customers—especially in enterprise—purchase products to avoid pain or reduce risk (e.g., missing revenue targets). GTM messaging should pivot from the "art of the possible" to risk mitigation to resonate more effectively with buyers.

The world of Fortune 500 executives is a small, interconnected community. Rather than casting a wide marketing net, focus all energy on securing one key 'lighthouse' customer. Over-deliver value for them, even if the deal isn't profitable. Their endorsement and introductions to peers are more effective than any marketing channel.

If a large customer drags out a pilot indefinitely, it's a sign that your solution isn't solving a visceral, high-priority pain. When the need is urgent, enterprises will "bulldoze" through internal bureaucracy to get the product into production quickly.

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.

Pursuing large "whale" customers for early validation is risky because they often come with heavy demands that can derail the product vision. Instead, seek out innovative, mid-level companies who are early adopters. They provide better feedback, and building traction with them opens doors to larger clients later.

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.

Chasing ten $10k deals over one $100k deal is a mistake. Smaller deals attract clients who nickel-and-dime you, don't fully buy into the vision, and provide distracting feedback. A single large deal provides a committed partner who will help guide your product roadmap.

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.