Head of Enablement & AI Self-Service

WinsAbove; United States; Hybrid; USD 190,000 - 355,000; Full time

Job summary

Toast seeks a Senior Director of Enablement to drive product activation, adoption, and self-service for Toast customers. You will own the Enablement vision and operating model across Learning Design, Knowledge Content Management, Customer Training and Certification, and Internal Enablement for Customer Success and Support teams.

You will lead the transformation for the AI era, co-own Toast's AI self-service strategy, and partner with Product and Customer Care to ensure knowledge becomes the AI

Qualifications

• 10+ years in education or enablement.
• At least 5 years leading leaders across multiple functions.
• Experience with learning strategy across modalities (e-learning, instructor-led, video, in-product).
• Experience leading knowledge management or content operations at scale, including AI-powered self-service.
• Hands-on use of generative AI tools in enablement or support roles.

Responsibilities

• Own Enablement vision, strategy and operating model across Learning Design, Knowledge Content Management, Customer Training & Certification, and Internal Enablement.
• Lead Enablement's AI-era transformation and define where AI vs. human judgment applies.
• Run data-driven intake and prioritization for enablement requests and route issues.
• Co-own Toast's AI self-service strategy and governance for knowledge content.
• Drive product activation and adoption by optimizing how customers learn and apply new knowledge.
• Lead enablement workstreams for product launches and enterprise-wide education.
• Own strategy and quality of Toast's knowledge content and self-help experiences.
• Reduce time to proficiency for new Care agents and Customer Success Managers.

Skills

Learning strategy

Instructional design

Content management

AI tools

Data analysis

Leadership

Change management

Cross-functional collaboration

Education

10+ years in education or enablement

Tools

Generative AI tools

Job description

Toast seeks a Senior Director of Enablement to drive product activation, adoption, and self-service for Toast customers. You will own the Enablement vision and operating model across Learning Design, Knowledge Content Management, Customer Training and Certification, and Internal Enablement for Customer Success and Support teams.

You will lead the transformation for the AI era, co-own Toast's AI self-service strategy, and partner with Product and Customer Care to ensure knowledge becomes the AI