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Enterprise AI Assistants are increasingly deployed in domains where accuracy is paramount, making each erroneous output a potentially significant incident. This paper presents a comprehensive framework for monitoring, benchmarking, and continuously improving such complex, multi-component systems under active development by multiple teams. Our approach encompasses three key elements: (1) a hierarchical ``severity'' framework for incident detection that identifies and categorizes errors while attributing component-specific error rates, facilitating targeted improvements; (2) a scalable and principled methodology for benchmark construction, evaluation, and deployment, designed to accommodate multiple development teams, mitigate overfitting risks, and assess the downstream impact of system modifications; and (3) a continual improvement strategy leveraging multidimensional evaluation, enabling the identification and implementation of diverse enhancement opportunities. By adopting this holistic framework, organizations can systematically enhance the reliability and performance of their AI Assistants, ensuring their efficacy in critical enterprise environments. We conclude by discussing how this multifaceted evaluation approach opens avenues for various classes of enhancements, paving the way for more robust and trustworthy AI systems.