CareerPlan

Senior Director of Enablement

Boston, Massachusetts, USAFull-time$173k2026-10-14 → 2026-11-10
Hybrid

Core

Senior leader driving product activation, adoption, and self-service for Toast's restaurant and local business customers while ensuring time-to-proficiency and role mastery for internal Customer Success and Support teams.

Role type

Senior Director of Enablement (Strategy & Operations)

Builds

AI-ready knowledge content, self-service experiences, and internal training programs for Customer Success and Support teams.

Domain

SaaS / Hospitality Technology / Customer Success

Required skills

Learning strategy, instructional design, knowledge management at scale, AI strategy, data-driven decision making, change management, executive communication, cross-functional leadership

Preferred skills

Generative AI tools fluency, product launch enablement, enterprise education initiatives

Technologies

Generative AI tools, e-learning platforms, instructor-led training systems, video training tools, in-product training modules

Responsibilities

Own the Enablement vision, strategy, and operating model across Learning Design, Knowledge Content Management, Customer Training, and Internal Enablement functions. Lead Enablement's transformation for the AI era by redefining workflows and building team AI fluency. Run a data-driven intake and prioritization process for enablement requests. Co-own Toast's AI self-service strategy with Product and Customer Care. Drive product activation and adoption by optimizing customer learning paths. Enable product launch readiness and enterprise-wide education initiatives. Shorten time to proficiency for new hires and advance role mastery for tenured employees.

Seniority

Senior Director, strategic leadership with hands-on operational oversight