• Define and execute the strategy for AI-driven, chat-based delivery of Toast’s educational content • Ensure content is structured, tagged, and optimized to support accurate, high-quality responses from AI models • Identifies opportunities to improve content and makes clear recommendations for actionable structural changes, content gap remediation, and content design improvements • Establish processes to continuously identify, prioritize, and close knowledge gaps surfaced through AI interactions • Serve as the Enablement organization’s subject-matter expert and point of contact for AI-related initiatives, tools, and partnerships • Lead the end-to-end program to increase customer self-service through educational content and AI-powered experiences • Establish operational rhythms, cross-functional coordination, and performance reporting to track adoption, impact, and outcomes • Identify, pilot, and scale initiatives that measurably improve self-service rates, customer self-sufficiency, content discovery, and support deflection • Own content discoverability and AI readiness strategy, defining structure and metadata standards to ensure content is indexed, surfaced, and to reduce inbound support demand • Lead optimization of non-text content (e.g., video transcripts, rich media) for AI and machine consumption as capabilities evolve • Leverage deflection data, search behavior, and customer intent signals to identify systemic gaps and opportunities across the content ecosystem • Audit high- and low-performing content to maximize self-service potential, with a focus on complex workflows and troubleshooting scenarios • Define, document, and enforce content standards, templates, and structural best practices to improve clarity, consistency, and usability across audience • Influence senior stakeholders as a trusted thought partner and authoritative source in AI-driven enablement and program management • Communicate program vision, tradeoffs, and outcomes clearly to audiences ranging from ICs to executive leadership