Toast
Senior Director of Enablement
$173K–$355K
Remote, United States +1 · Remote · Director · Full-time · Posted Oct 14, 2026
- Location
- Remote, United States
Boston, MA, United States - Experience
- 10+ years in education or enablement; at least 5 years leading leaders across multiple functions.
About the job
Leads Toast’s Enablement strategy and operations to improve customer product adoption and self-service, and accelerate employee proficiency and role mastery.
What you'll do
- Own the vision, operating model, and performance reporting for learning design, knowledge content, customer training and certification, and internal enablement.
- Lead Enablement’s AI transformation and co-own AI self-service strategy, including AI-ready knowledge standards, governance, and performance feedback loops.
- Improve customer activation, adoption, and self-service, and employee proficiency and performance through data-driven enablement and launch education.
What they ask for
- 10+ years in education or enablement, including at least 5 years leading leaders across multiple functions.
- Experience with learning strategy, instructional design, and training delivery across modalities.
- Experience leading a large-scale knowledge management or content operation, including for AI-powered self-service.
- Hands-on experience using generative AI tools in enablement or support work.
Pay
$222,000 — $355,000 USD (base salary); $192,000 — $307,000 USD (base salary); $173,000 — $277,000 USD (base salary)
AI focus
Lead Enablement’s AI transformation; decide where AI or human judgment and validation are appropriate; build team AI fluency; co-own AI self-service strategy; set and govern AI-ready knowledge standards and use AI performance data to improve content.
Model-written summary · the original posting is authoritative