Principal Enablement Program Manager, Toast

• 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

Desirable

• The AI & Self-Service Program Manager is responsible for optimizing Toast’s educational content ecosystem to maximize customer self-service, improve knowledge discovery, optimize how AI leverages the content, and reduce reliance on human support
• This role leads the strategic delivery of education through AI-powered experiences while ensuring content is structured for effective consumption by customers, support agents, and search engines
• By optimizing content for AI models, human readability, and SEO, this role ensures educational resources are easy to discover, easy to understand, and easy to act on
• The Program Manager serves as the technical architect for Toast’s content ecosystem, defining the structural and metadata standards that ensure content is discoverable, machine-readable, and optimized for AI-driven customer outcomes
• The Program Manager also represents the Enablement organization in cross-functional AI initiatives (e.g., Toast Now, Toast IQ), helping define and scale how AI tools leverage enablement content to improve customer outcomes
• This role serves as a thought leader within the Enablement organization and a trusted cross-functional partner across Product, Support, Marketing, and AI platform teams
• By applying a deep understanding of Toast’s business model, customer pain points, and the broader AI landscape, this role delivers program strategies that drive measurable impact at scale
• 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