Director, AI Transformation

About the role

Toast is actively seeking a Director, AI Transformation to own the end-to-end strategy and execution of AI across the company in a hands-on capacity. This role is responsible for translating the CEO's vision into a practical roadmap that drives real adoption and measurable business impact starting with AI fluency across thousands of employees. You will act as a thought partner to the CEO and senior leadership team while also serving as a hands-on builder of workflows and tools. The position requires equal parts strategic thinker, operational executor, and cultural leader who can build alongside teams rather than direct them from a distance. You will own the narrative of how AI reshapes our business and ensure that this narrative becomes reality through concrete actions and results.

Key facts

What you'll do

You will own Toast's company-wide AI transformation strategy, defining the roadmap from initial fluency to impactful business outcomes while establishing the North Star metric for adoption in 2026 and advising the CEO and Chief of Staff on where to focus efforts. You will act as a player-coach, building capability by doing the work side-by-side with teams and lifting every function rather than only your own area of responsibility. As the eminent hands-on builder, you will personally design enablement programs and construct agentic workflows and tools that deliver fast value to Toasters, setting the standard for quality and effectiveness across the organization. You will think like a technologist, helping our R&D teams scope, build, and stress-test platforms such as internal app hosting that scale our impact and ensure robust, reusable infrastructure. You will manage up, down, and around the organization, partnering with and influencing leaders at the SVP and C-suite levels while also embedding AI into how their teams operate on a daily basis. You will run the operating rhythm and cultural infrastructure of the AI function, including enablement cohorts, leadership offsites, internal wins channels, shared use-case and prompt libraries, and feedback loops that convert early energy into lasting standard practice. You will own the economics of AI transformation by tracking platform spend and usage against budget and modeling the cost of scaling adoption in a way that is both deep and cost-effective for the business. Finally, you will build the AI function itself, defining what Toast's AI team should become and growing from doing the work personally to leading a high-performing group that sustains momentum.

Requirements

You must possess deep, hands-on AI fluency, with the ability to build agentic workflows yourself, paired with strong conceptual and analytical problem-solving skills and an unmatched hunger to move the needle incrementally every single day, which is a non-negotiable part of this role. You need a track record of driving change across a large, complex organization and influencing senior leaders at the VP, SVP, and C-suite levels without relying on formal authority to get things done. You should be capable of taking ambiguous, messy business processes and reducing them to structured, actionable parts that can be immediately acted upon using AI and automation. A player-coach instinct is essential, as you must make the people around you measurably better by working alongside them rather than simply managing their output. The ideal candidate brings 10+ years of experience across consulting, strategy and operations, product, or another build-oriented discipline that provides a foundation for understanding how technology creates business value at scale. You must be comfortable operating at the intersection of business and technology, able to communicate effectively with both technical and non-technical stakeholders while maintaining rigor in your thinking and execution. Strong judgment and discretion are required when working with sensitive business information, executive perspectives, and cross-functional dependencies that span the entire organization. You will be expected to uphold the high standards of Toast by demonstrating ownership, clarity, and resilience in the face of complex, evolving challenges.

Practical notes

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