Senior Director of Enablement

Toast

. Own the Enablement vision, strategy, and operating model across Learning Design, Knowledge Content Management, Customer Training and Certification, and Internal Enablement .

Posted 10/14/2026full-timeUnited StatesSenior💰 $173,000 - $355,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in Learning Strategy, Instructional Design, and Training Delivery, with a strong focus on AI integration and knowledge management. Proven ability to lead cross-functional teams and drive measurable business outcomes through effective enablement strategies.

Highest-signal resume keywords

Learning StrategyInstructional DesignKnowledge ManagementGenerative AI ToolsMetrics Definition and Interpretation

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Learning StrategyInstructional DesignTraining DeliveryKnowledge ManagementAI-Powered Self-ServiceMetrics DefinitionData-Driven Decision MakingContent OperationsE-Learning DevelopmentIn-Product Training

Soft Skills

Excellent Written CommunicationExcellent Verbal CommunicationCredibility with ExecutivesTrust BuildingCross-Functional Collaboration

Industry Keywords

EnablementCustomer SuccessProduct ActivationContinuous ImprovementOperating Model Change

About the role

Key responsibilities & impact

Own the Enablement vision, strategy, and operating model across Learning Design, Knowledge Content Management, Customer Training and Certification, and Internal Enablement
Report Enablement impact to Toast senior leadership using metrics tied to quantified business outcomes
Lead Enablement's transformation for the AI era and determine where AI and human judgment should be used
Build the team's AI fluency and drive continuous improvement
Run a transparent, data-driven intake and prioritization process for enablement requests
Diagnose root causes and route non-enablement issues to the appropriate owners
Co-own Toast's AI self-service strategy with Product and Customer Care
Set standards and governance for AI-ready knowledge and turn AI performance data into content improvements
Drive customer product activation and adoption
Lead enablement for product launches and enterprise-wide education initiatives
Own the strategy and quality of knowledge content and self-help experiences
Shorten time to proficiency for new Care agents and Customer Success Managers
Advance role mastery for tenured Toasters through continuous enablement

Requirements

What you’ll need

10+ years in education or enablement
At least 5 years leading leaders across multiple functions
Extensive experience with learning strategy, instructional design, and training delivery across e-learning, instructor-led, video, and in-product modalities
Experience leading knowledge management or content operations at scale, including AI-powered self-service
Understanding of frontline Support agents, Customer Success Managers, and how customers learn and adopt software
Hands-on experience using generative AI tools in enablement or support work
Track record of leading a team through a significant operating-model change
Ability to define metrics, interpret results, and connect enablement inputs to customer and business outcomes
Ability to establish credibility and trust with executives, cross-functional partners, and frontline managers and employees
Excellent written and verbal communication

Benefits

Comp & perks

Competitive compensation and benefits programs
Cash compensation, including overtime and bonus/commissions if eligible
Equity
Benefits supporting a healthy lifestyle
Flexible benefits to meet changing needs
Hybrid work model valuing individual needs
Accessible and inclusive hiring process
Reasonable accommodations for persons with disabilities