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Senior Director of Enablement

Toast

Remote · Boston · 10+ years experience · Posted Oct 14, 2026

At a glance

Experience
10+ years experience
Location
Remote · Boston

About the role

  • The Senior Director of Enablement is a senior leader responsible for driving product activation, adoption, and self-service for Toast's customers.
  • This leader owns the vision, operating model, and execution of Enablement across Learning Design, Knowledge Content Management, Customer Training and Certification, and Internal Enablement.
  • A major focus of this role is leading Enablement's transformation for the AI era and co-owning Toast's AI self-service strategy.

Responsibilities

  • Own the Enablement vision, strategy and operating model across Learning Design, Knowledge Content Management, Customer Training and Certification, and Internal Enablement functions.
  • Report Enablement's impact to Toast senior leadership using metrics tied to quantified business outcomes.
  • 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.
  • Drive product activation and adoption by optimizing how customers discover, learn and apply new knowledge.
  • Enable Toast to maintain a high rate of innovation by leading the enablement workstream 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 by building foundational knowledge, skills, tools, and process proficiency.
  • Advance role mastery for tenured Toasters through continuous enablement across role skills, product knowledge, and process and tool adoption.

Requirements

  • 10+ years in education or enablement, with at least 5 years leading leaders across multiple functions.
  • Extensive 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 how frontline Support agents and Customer Success Managers operate day to day, and how customers learn and adopt software.
  • Hands-on experience using generative AI tools in enablement or support work, with a clear view of where they perform well and where they do not.
  • Track record of leading a team through a significant change in its operating model.
  • Comfortable working with data: defining metrics, interpreting results, and connecting enablement inputs to customer and business outcomes.
  • Able to establish credibility and trust with executives, cross-functional partners, and frontline managers and employees.
  • Excellent written and verbal communication.

Workplace

  • Remote; Boston
  • Embraces a hybrid work model that fosters in-person collaboration while valuing individual needs.

Skills

  • Generative AI
  • Instructional Design
  • Knowledge Management

Toast

Senior Director of Enablement

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