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.

To credibly sell to the largest enterprises from day one, Sierra intentionally hired experienced executives. The crucial filter was selecting for "competitive intensity" and high agency, avoiding the political mindset often associated with big-company hires. This allowed them to land massive customers early.

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.

Stop targeting the ambiguous "mid-market." Your strategy, hiring, and ACV must align with either a marketing-led SMB motion or a sales-led enterprise motion. Blending them leads to failure as they are distinctly different games.

An HR tool failed in the general market but took off with plumbing and HVAC companies. These businesses are 'structurally understaffed,' meaning their problem is persistent and acute. They have a burning, unmet need, unlike general customers who are 'kind of okay' with their current solutions and lack urgency.

The process of defining a GTM strategy isn't just about choosing which segments to target; it's equally about deciding which ones to ignore. Failing to actively say "no" creates fuzziness, dilutes resources, and leads to misaligned sales and marketing efforts downstream.

At the $300k revenue stage with one salesperson, defining a precise Ideal Customer Profile isn't just for targeting. It's a survival mechanism to focus limited resources, prevent churn, and ensure every sales effort contributes to scalable growth, rather than creating future service burdens that consume your only salesperson.

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.

In every industry, a few established enterprises—like Costco for HR software—act as 'tastemakers' by adopting new technology early. Winning these key accounts first provides crucial validation and influences other companies in the vertical to follow, creating a powerful go-to-market advantage that bypasses smaller customers.