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.

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.

A MedTech startup's initial go-to-market may be hospital-by-hospital sales. However, after building a robust evidence base of clinical and economic impact, the sales focus can shift to enterprise-level deals with regional or national healthcare systems, accelerating growth.

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.

While conventional wisdom suggests moving upmarket for growth, Sensei chose the opposite path to scale from $40M to $100M ARR. They partnered with Pax8 to target a vast number of smaller customers downstream, leveraging the channel's reach for a "10x proposition" without the heavy investment required for enterprise sales readiness.

Instead of starting with a scalable platform, Decagon built bespoke, perfect solutions for its first few enterprise customers. This validated their ability to solve the core problem deeply. Only after proving this value did they abstract the common patterns into a platform.

Instead of launching a full platform, Canary Technologies began by digitizing a single, tedious process: credit card authorization forms. This "bite-sized" approach allowed them to solve a tangible pain point, build trust, and "earn their right" to sell more complex solutions to hoteliers later.