Five9 Explains How Human-in-the-Loop AI Drives Better CX Outcomes

Where should AI automation stop, and where does human judgment still matter most?

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AI & Automation in CXInterview

Published: June 24, 2026

Nicole Willing


In this CX Today interview, Nicole Willing speaks with Jonathan Rosenberg, Chief Technology Officer at Five9, about the role of human-in-the-loop design in AI-powered customer experience.

Rosenberg explains why mature AI strategies should not treat human intervention as a failure or last resort. Instead, humans play a critical role in continuous learning, governance, high-risk decisions, and customer interactions where emotion, complexity, or value requires a human touch. The conversation explores why businesses should avoid chasing 100 percent automation, how AI can still support agents when interactions are handed over, and why CX leaders need stronger auditing, monitoring, and performance evaluation as AI agents become more common.

Rosenberg also shares practical advice for organizations beginning their AI journey: start with simple, high-confidence use cases, prove value, build oversight structures, and then expand carefully.

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