Every team is building agents. Far fewer are shipping ones that reliably drive outcomes. The next frontier isn't more agents - it's agents that close the loop on real work. At RingCentral, I've scaled our AI Assistant from passive note-taker to a swarm of outcome-driving agents. Before that, at my quant trading firm, I built self-correcting agents that autonomously improved strategy performance, teaching me that real value isn't in the report, it's in what the system does next. We'll map the maturity curve from passive summarization to proactive action, walk through the agent architecture that powers outcome-driven collaboration, and confront the hard accuracy problems most teams underestimate - context collapse, intent drift, and cascading errors in multi-step workflows. Attendees will leave with a KPI framework for measuring AI agent ROI and a concrete roadmap for getting their agents from unreliable to production-ready.