Senior Director of Enablement

The posting, as Toast wrote it

Toast creates technology to help restaurants and local businesses succeed in a digital world, helping business owners operate, increase sales, engage customers, and keep employees happy. At Toast, we are passionate about innovation, excellence, and building a community of customers and employees who love what they do.

The Senior Director of Enablement is a senior leader responsible for driving product activation, adoption and self-service for Toast's customers. They are also accountable for time-to-proficiency and role mastery for the Toasters who serve them, so that every customer has a great experience with Toast. In order to accomplish these goals, this leader owns the vision, operating model and execution of Enablement across its functions: Learning Design, Knowledge Content Management, Customer Training and Certification, and Internal Enablement (New Hire Enablement and Continuous Enablement) for our Customer Success and Support teams.

A big part of this role is leading Enablement's transformation for the AI era, evolving and innovating on how each function produces, delivers and measures its work. This leader will also co-own Toast's AI self-service strategy in close collaboration with Product and Customer Care, since the knowledge Enablement creates is the “brain” of our AI self-service experiences.

This is a highly visible role that works closely with senior leaders across the organization, and is accountable for Enablement's impact on both customer outcomes (activation, adoption, self-service rate, support contact rate) and Toaster outcomes (time to proficiency, role mastery, and Support and Customer Success performance).

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. Decide where AI does the work and where people add judgment and validation, and build the team's AI fluency to drive continuous improvement.
• Run and refine a transparent, data-driven intake and prioritization process for enablement requests. Diagnose root causes and route non-enablement issues (process, product, policy, tooling) to the correct owners.
• Co-own Toast's AI self-service strategy with Product and Customer Care. Set the standards for AI-ready knowledge (coverage, structure, accuracy, freshness), establish the governance to maintain them as the product changes, and run the feedback loop that turns AI performance data into content improvements.
• 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 enter

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sks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. We ask that you complete interviews and assessments on your own, without real-time AI tools, recording, or transcription bots, unless we tell you otherwise in advance. To learn more: https://careers.toasttab.com/ai-in-hiring

Our Approach to Hybrid Working

We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the hospitality community, regardless of location. Please visit the Locations page on our career site to learn more about our in-office expectations by region: https://careers.toasttab.com/locations-toast

People Are the Secret Ingredient in Our Recipe for Success

At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry brings together people with a wide range of backgrounds, experiences, and perspectives, and we value that same breadth at Toast. We strive to build a culture grounded in authenticity, respect, and humility, where every Toaster has a real opportunity to grow, contribute, and do their best work—raising the bar in delivering exceptional experiences for our customers and each other.

Apply today!

Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com .

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