A common PLG pitfall is assuming the user base will naturally springboard into enterprise deals. Often, the enterprise buyer is a different person with different problems. This oversight can cost companies years, as they have to build a second, separate sales motion from scratch.
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Even successful PLG companies like Figma eventually burn through their early adopter market. To avoid hitting an asymptotic growth curve, they must proactively build a traditional outbound sales team to tackle the enterprise market before the PLG engine stalls. Don't wait until you need it.
Founders must consider their sales motion (e.g., PLG vs. enterprise sales-led) when designing the product. A product built for one motion won't sell effectively in another, potentially forcing a costly redesign. This concept extends "product-market fit" to "product-market-sales fit."
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.
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.
Avoid pursuing prosumer and enterprise motions simultaneously. The optimal sequence is to first build massive bottoms-up love and brand trust with individual users. This creates internal champions within target companies, providing crucial momentum and turning a cold B2B sale into a pull-based motion.
Selling a small, cheap "land" deal to an enterprise customer is dangerous. When you try to expand, they will question the 10x price jump, making it nearly indefensible. Start with a price ($75k-$150k) that reflects enterprise value to avoid being trapped by a low initial anchor.
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.
Enterprises are comfortable buying services. Sell a service engagement first, powered by your technology on the back end, to get your foot in the door. This builds trust and bypasses procurement hurdles associated with new software. Later, you can transition them to a SaaS product model.
Successful sales leaders don't just copy-paste their old playbook. They adapt it using first principles, considering the new company's specific product, user behavior, and GTM motion (like PLG). Rigidity is a common mistake that leads to failure.
To create transformational enterprise solutions, focus on the core problems of the key buyers, not just the feature requests of technical users. For healthcare payers, this meant solving strategic issues like care management and risk management, which led to stickier, higher-value products than simply delivering another tool.
