Prepared tackled the slow GovTech market by providing its initial product for free. This strategy bypassed cumbersome procurement, built a large user base, and established the credibility needed to overcome the authority of entrenched, larger competitors.

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.

In a B2B context, the most effective freemium products don't just offer a limited tool. They act as a diagnostic, giving away value by clearly identifying a painful hole in the user's business—a hole your paid product is designed to fill.

Egnyte demonstrates an alternative to the perpetual fundraising cycle. After a 2018 round, the company scaled to "several hundred million" in ARR and achieved Rule of 40 status through EBITDA-positive growth, proving that massive scale can be achieved via capital efficiency.

Don't fight battles you can't win. For a product like Evernote, competing with free, pre-installed apps like Apple Notes for casual users is a losing proposition. The winning strategy is to focus on the advanced user segment whose complex needs justify paying for a more powerful tool.

Figma delayed monetization to accelerate growth. However, enterprise customer Microsoft stated they couldn't depend on critical free software that might go out of business. This customer pressure was the catalyst for Figma to implement a pricing model, proving viability is key for enterprise adoption.

The founder of AI content startup Dream Stories deliberately rejected the common VC-fueled model of offering free, subsidized products. By charging customers from the beginning, he forced the business to find immediate product-market fit and build a sustainable economic model, grounding the company in real-world validation rather than burning cash on an unproven concept.

Promote IQ succeeded by targeting large retailers, a market other startups avoided due to its notoriously difficult and long sales cycle. They turned this pain point into a strategic advantage. By mastering the difficult sales process, they created a high barrier to entry that gave them time and space to dominate the category before competitors could catch up.

While the market rushed to pure-cloud solutions, Egnyte offered a hybrid model. This wasn't a compromise but a strategic advantage for enterprises where physics, like network latency on a construction site, made pure-cloud impractical. The control plane remained in the cloud, while the data plane could be local.