The freemium business model has become the dominant go-to-market strategy for software-as-a-service (SaaS) companies, yet the majority of firms employing this approach achieve conversion rates of only two to five percent, raising critical questions about optimal freemium design. This case study examines the freemium strategy evolution of CloudMetrics, an anonymized business-to-business SaaS analytics platform that grew from $1.2 million to $14.8 million in annual recurring revenue over a three-year period following its transition from a free-trial model to a freemium offering. Drawing on the theoretical frameworks of network externalities, consumer value theory, and product-led growth, this study traces four distinct phases of CloudMetrics' freemium optimization: an initial feature-gated model, the introduction of usage limits, a hybrid combining both dimensions, and a product-led growth strategy with personalized conversion triggers. The analysis reveals that the hybrid freemium model produced the highest marginal improvement in conversion rates, increasing free-to-paid conversion from 3.8 percent under a feature-only model to 7.4 percent under the fully optimized product-led approach. The case further demonstrates that freemium-acquired customers exhibited 127 percent net revenue retention, substantially exceeding the 109 percent observed among sales-led cohorts. These findings support four research propositions concerning the superiority of hybrid freemium designs, the role of within-organization network effects in amplifying usage-based conversion, the existence of an optimal conversion trigger timing window, and the higher post-conversion quality of freemium-acquired customers. Managerial implications for SaaS practitioners designing and iterating freemium strategies are discussed.