Generative AI (GenAI) is increasingly captivating enterprises with its potential to enhance productivity and innovation, yet many promising initiatives falter in "pilot purgatory," unable to transition from experiments to scalable, production-ready systems delivering tangible business value. This disconnect is not due to the technology itself but rather a lack of enterprise readiness for operationalization, requiring accountability and demonstrable ROI. Challenges in scaling GenAI include technical and organizational hurdles such as poor data quality, security and compliance issues, inadequate MLOps, and a lack of cross-functional collaboration. Successful operationalization demands a holistic strategy that addresses technology, data, security, process, people, and governance, while also emphasizing domain-specific customization, human oversight, and modular architecture. Organizations that effectively address these challenges, such as Persistent Systems and Morgan Stanley, demonstrate that scalable GenAI is achievable through purpose-built systems and strategic partnerships. Ultimately, transitioning GenAI from pilot to production requires a strategic transformation with a focus on building robust AI systems designed to deliver real business value.