Senior Director of Enablement

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 enterprise-wide education initiatives so customers, agents and CSMs are ready at release. • Enable customer self-service by owning the strategy and quality of Toast's knowledge content and self-help experiences, measured by Self-Service Rate, content gaps and support contact rate. • Shorten time to proficiency for new Care agents and Customer Success Managers by building the foundational knowledge, skills, tools and process proficiency every new hire needs. • Advance role mastery for tenured Toasters through continuous enablement across role skills, product knowledge, and process and tool adoption, to improve Support outcomes (Customer Satisfaction, Time to Resolve, First Contact Resolution) and Customer Success outcomes (Product Adoption and Retention). 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. 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 componen