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, starting with everyday fluency across thousands of Toasters, and leading to real and measurable business impact. It's one of the company's top priorities from the CEO, and this person owns it end to end: a thought partner to the CEO and senior team, a dotted-line leader over the existing set of department-level AI leaders (all Director- and Senior Director-level), and a builder at ground level with each of our functional teams.

The role calls for an unusual mix of skills, and we're holding a high bar for it. The strongest candidate, regardless of background, is equal parts:

• AI-native builder and conceptual thinker - fluent enough with agentic tools to build real workflows themselves, structured enough to break a messy, cross-functional business process into parts that can be automated or streamlined with AI, and sharp enough to do this outside their domain of expertise with little prep.
• Builder and coach - someone who can 10x their own output and, just as important, lift the people around them by building with them rather than for them.
• Operator who manages up, down, and around - as comfortable advising and challenging at the SVP / C-suite level as they are in the weeds driving enablement and adoption with the front lines.

In practice the balance shifts day to day: building enablement and shipping tooling one day, coaching a VP's team to its first working automation the next, advising the CEO and Chief of Staff on where to place the next internal AI bet after that. We're looking for someone who can move across all three without missing a step.

Responsibilities

• 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.
• Own the economics - track platform spend and usage against budget, and model the cost of scaling adoption that's both deep and cost-effective.
• Build the function - define what Toast's AI team should become, and grow from doing the work yourself into leading the team that does it.

Requirements

• 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.
• 10+ 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.

Our Spread of Total Rewards

• Flexible Vacation
• Sabbatical opportunity after five years
• Professional Development Reimbursement Program
• Commitment to Employee Wellness through resources such as a quarterly Wellness Stipend
• Various peer and company recognition programs
• 401(k) and matching
• Medical, Dental, & Vision Coverage
• Mental Health Benefits
• Subsidized backup childcare