Senior Director, Enablement & AI Transformation

Toast; United States; Hybrid; USD 173,000 - 355,000; Full time

Benefits offered by this job

Hybrid work model

Job summary

Toast is seeking a Senior Director of Enablement to lead product activation, adoption, and self-service strategies for customers and internal teams. This role owns the enablement vision across Learning Design, Knowledge Content Management, Customer Training and Certification, and Internal Enablement, aligning with Toast’s AI self-service goals.

The leader will drive transformation, establish metrics, and partner with Product and Customer Care to ensure high time-to-proficiency, rapid adoption,

Qualifications

• 10+ years in education or enablement.
• Experience leading leaders across multiple functions.
• Experience with learning strategy, instructional design and multi-modality delivery.
• Knowledge management or content operation at scale, including AI-powered self-service.
• Understanding frontline Support and Customer Success workflows.
• Hands-on use of generative AI tools in enablement or support.
• Proven track record of guiding organizational change in operating models.
• Ability to define metrics, interpret data and tie enablement to outcomes.
• Credible with executives and cross-functional partners; strong communication.

Responsibilities

• Own Enablement vision, strategy and operating model across Learning Design, Knowledge Content Management, Customer Training and Certification, and Internal Enablement.
• Lead AI-era transformation, decide where AI works and where human judgment is needed.
• Run data-driven intake and prioritization for enablement requests.
• Co-own AI self-service strategy with Product and Customer Care; govern content quality.
• Drive product activation and adoption by improving how customers learn and apply knowledge.
• Lead enablement for product launches and enterprise education initiatives.
• Own strategy and quality of Toast's knowledge content and self-help experiences.
• Decrease time to proficiency for new Care agents and Customer Success Managers.
• Advance role mastery through ongoing enablement to improve customer outcomes.

Skills

Learning strategy

Instructional design

Training delivery

Knowledge management

AI enablement

Data-driven decisions

Executive communication

Tools

AI tools

Job description

Toast is seeking a Senior Director of Enablement to lead product activation, adoption, and self-service strategies for customers and internal teams. This role owns the enablement vision across Learning Design, Knowledge Content Management, Customer Training and Certification, and Internal Enablement, aligning with Toast’s AI self-service goals.

The leader will drive transformation, establish metrics, and partner with Product and Customer Care to ensure high time-to-proficiency, rapid adoption,