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.

The popular pursuit of massive user scale is often a trap. For bootstrapped SaaS, a sustainable, multi-million dollar business can be built on a few hundred happy, high-paying customers. This focus reduces support load, churn, and stress, creating a more resilient company.

Focusing on individual enterprise client needs creates conflicting workflows that hinder scalability. A successful transition involves moving to a user research-driven approach, using data to justify a standardized product direction that serves the broader market, not just a few powerful clients.

General Catalyst's CEO notes a change in enterprise AI GTM strategy. The old model was finding product-market fit, then repeating sales. The new model involves "forward deployed engineering" to build deep trust with an initial enterprise client, then focusing on expanding the services offered to that single client.

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.

Fathom's strategy was to build a robust system for meeting capture and processing, anticipating that transcription costs would drop and GenAI would mature. When GPT-4 launched, they simply "dropped in the engine" to their pre-built "sports car," instantly upgrading their value and triggering explosive growth from $1M to $10M ARR.

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.

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.