Senior Director of Enablement

About this role

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.