Senior Director, AI Enablement & Customer Growth

Toast Tab, Inc.; United States; On-site; USD 190,000 - 355,000; Full time

Benefits offered by this job

Hybrid work model

Equity

Benefits

Job summary

Toast Tab, Inc. is seeking a Senior Director of Enablement to lead product activation, adoption, and AI-enabled self-service for customers.

You will own the vision, operating model, and execution across Learning Design, Knowledge Content Management, Customer Training, and Internal Enablement for Customer Success and Support teams. You will co-own Toast's AI self-service strategy with Product and Customer Care, defining AI-ready knowledge standards and governance, while driving data-driven

Qualifications

• 10+ years in education or enablement with at least 5 years leading leaders across multiple functions.
• Experience with learning strategy, instructional design and training delivery across modalities (e-learning, instructor-led, video, in-product).
• Experience leading a knowledge management or content operation at scale, including for AI-powered self-service.
• Understanding of frontline Support agents and Customer Success Managers operations.
• Hands-on experience using generative AI tools in enablement or support work.
• Track record of leading a team through a significant change in its operating model.
• Comfortable working with data: defining metrics, interpreting results, and linking enablement inputs to outcomes.
• Excellent written and verbal communication.

Responsibilities

• Own the Enablement vision, strategy and operating model across Learning Design, Knowledge Content Management, Customer Training and Certification, and Internal Enablement functions.
• Lead Enablement's transformation for the AI era by redefining how each function produces, delivers and measures its work.
• Run and refine a transparent, data-driven intake and prioritization process for enablement requests.
• Co-own Toast's AI self-service strategy with Product and Customer Care, establishing governance and continuous improvement loops.
• Drive product activation and adoption by optimizing how customers discover, learn and apply new knowledge.
• Lead enablement workstreams for product launches and enterprise-wide education initiatives.
• Enable customer self-service by owning the strategy and quality of Toast's knowledge content and self-help experiences.
• Shorten time to proficiency for new Care agents and Customer Success Managers.
• Advance role mastery through continuous enablement across role skills and process adoption.

Skills

Learning strategy

Instructional design

Training delivery

Knowledge management

AI in enablement

Data analysis

Change management

Executive communication

Problem solving

Tools

Generative AI tools

Job description

Toast Tab, Inc. is seeking a Senior Director of Enablement to lead product activation, adoption, and AI-enabled self-service for customers.

You will own the vision, operating model, and execution across Learning Design, Knowledge Content Management, Customer Training, and Internal Enablement for Customer Success and Support teams. You will co-own Toast's AI self-service strategy with Product and Customer Care, defining AI-ready knowledge standards and governance, while driving data-driven