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Own the vision, strategy, and operating model for all Enablement functions—including Learning Design, Knowledge Content, Customer Training, and internal onboarding—while reporting impact through data‑driven metrics. Lead the AI‑era transformation of those functions and co‑own Toast’s AI self‑service knowledge strategy. Run a transparent intake and prioritization process for enablement requests and ensure AI‑ready content quality.
10+ years in education or enablement with at least 5 years leading leaders across multiple functions, strong background in learning strategy, instructional design, and large‑scale knowledge management (including AI‑powered self‑service). Must be data‑savvy, comfortable with executive stakeholders, and have hands‑on experience using generative AI tools in enablement or support contexts.
The role directly drives product activation, adoption, and self‑service rates, while shortening time‑to‑proficiency and boosting role mastery for Customer Success and Support teams. Its impact is measured in key customer outcomes (activation, adoption, support contact rate) and internal performance metrics (time to proficiency, satisfaction, resolution rates), making it critical to Toast’s growth and customer success.
A senior leader who thrives on leading cross‑functional teams through major operating‑model changes, is fluent in AI‑enabled content creation, and excels at turning data into actionable enablement strategies. Ideal for someone with strong communication skills, executive credibility, and a passion for building scalable learning and knowledge systems.
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).
AI at Toast
At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture.
Our Total Rewards Philosophy
We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits.
The base salary range for this role is listed below. The starting salary will be determined based on skills, experience, and geographic location. In addition to base salary, our total rewards components include cash compensation (overtime, bonus/commissions if eligible), equity, and benefits. You can learn more about how we align pay with local labor markets in our Geographic Pay Zone Philosophy.
How Toast Uses AI in its Hiring Process
Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks 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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