The opportunity
Toast is driven by building a platform that helps restaurants adapt, take control, and get back to what they do best: building the businesses they love. The Office of the CEO is hiring a Director, AI Transformation to lead - hands-on - how AI changes the way Toast works,…
What you'll do
Own Toast's company-wide AI transformation strategy: the roadmap from fluency to business impact, and the North Star metric that measures it (adoption in 2026), advising the CEO and Chief of Staff on where to push.
Coach and scale the org: work as a player-coach who builds capability by doing the work alongside teams, lifting every function versus just their own.
Be the eminent hands-on builder: personally design enablement and build agentic workflows and tools that get Toasters to real value fast, setting the bar for what great looks like across the company.
Think like a technologist: not only building one-off tooling, but helping our R&D teams scope, build, and stress-tests the platforms that scale our impact as an org (i.e., internal app hosting)
Manage up, down, and around: partner with, influence, and hold accountable leaders across the SVP- and C-level, embedding AI into how their teams operate.
Run the operating rhythm and cultural infrastructure: whether through enablement cohorts, leadership offsites, internal wins channels, shared use-case and prompt libraries, and the feedback loops that turn early energy into standard practice.
What they're looking for
- The combination at the heart of the role: deep, hands-on AI fluency - you build agentic workflows yourself - paired with strong conceptual and analytical problem-solving and an unmatched hunger to move the needle, incrementally, every single day. This is the part we won't compromise on.
- A track record of driving change across a large, complex organization, and of: influencing senior leaders (VP / SVP / C-suite) without formal authority.
- The ability to take an ambiguous, messy business process, reduce it to: structured, actionable parts - then act on it.
- A player-coach instinct: you make the people around you measurably better, not just yourself.
- + years across consulting, strategy and operations, product or another: builder role, or fast-growth tech. We're hiring for capability and ceiling, not pedigree.
- Exceptional written communication: you can make complex, technical topics clear to a non-technical executive audience.
- Proactive and resourceful, with a high bar on pace; comfortable with: ambiguity, quick to take a first pass and create momentum, and able to define the role as you go.
