Principal Enablement Program Manager, AI & Self-Service at Toast

Toast

Remote·8h ago

LeadFull-timeRustGitGoAI

Salary Range

$108,375 - $146,625 /year

Estimated

This salary is estimated based on similar roles. The actual salary may vary.

About the Role

The AI & Self-Service Program Manager at Toast is responsible for optimizing the company’s educational content ecosystem to maximize customer self-service, improve knowledge discovery, and optimize how AI leverages the content. 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.

Key Responsibilities

→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
→Identify opportunities to improve content and make recommendations for actionable structural changes
→Establish processes to continuously identify, prioritize, and close knowledge gaps
→Serve as the Enablement organization’s subject-matter expert for AI-related initiatives
→Lead the end-to-end program to increase customer self-service through educational content and AI-powered experiences
→Identify, pilot, and scale initiatives that improve self-service rates and content discovery
→Own content discoverability and AI readiness strategy
→Lead optimization of non-text content for AI and machine consumption
→Leverage deflection data and search behavior to identify systemic gaps and opportunities
→Audit high- and low-performing content to maximize self-service potential
→Define and enforce content standards, templates, and structural best practices
→Influence senior stakeholders as a trusted thought partner
→Communicate program vision and outcomes clearly to various audiences

Requirements

✓8+ years of experience in program management, enablement, or related discipline
✓Proven experience owning complex, cross-functional programs
✓Experience applying AI, automation, or search technologies to content delivery
✓Experience working with AI-powered chat, voice AI, search, or knowledge platforms
✓Strong data and analytical skills
✓Exceptional communication and stakeholder-influencing skills
✓Advanced experience with knowledge-related tech and tools
✓Advanced knowledge and experience with information architecture