Principal Enablement Program Manager, AI & Self-Service

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy.

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.

A day in the life (Responsibilities):

AI & Chat-Based Knowledge Delivery

• 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

Self-Service & Content Discovery

• 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

Content Optimization & Governance

• 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, Communication & Leadership

• 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

What you'll need to thrive (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 

Nice To Haves

• Self-motivated with a relentless “fixer” mindset
• Ability to see the big picture and problem-solve the root cause, not just the immediate symptom
• Familiar with and empathetic to the restaurant customer experience
• Passion for research and curiosity that calls you to go beyond “good enough” to create something innovative and exciting

AI at Toast

At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.

Our Total Rewards Philosophy

We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.