Principal Enablement Program Manager, AI & Self-Service

Role Overview

• 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

Requirements

• 8+ years of experience in program management, enablement, knowledge management, content strategy, or related discipline
• Proven experience owning complex, cross-functional programs that drive measurable business outcomes
• Experience applying AI, automation, or search technologies to content delivery, discovery, or support deflection use cases
• Experience working with AI-powered chat, voice AI, search, or knowledge platforms (e.g., in-product assistants, support bots, or LLM-based tools)
• Strong data and analytical skills, with experience using customer intent signals, engagement data, and performance metrics to guide prioritization and optimization
• Exceptional communication and stakeholder-influencing skills, with the ability to partner effectively across Product, Support, Marketing, and technical teams
• Advanced experience with knowledge-related tech and tools, such as Coveo, Salesforce Service Cloud, Intercom, and Contentful
• Advanced knowledge and experience with information architecture as it relates to a knowledge base and how content is organized

Tech Stack

• Cloud

Benefits

• Competitive compensation and benefits programs
• Health insurance
• 401(k) matching
• Flexible working hours
• Paid time off