Director, AI Transformation (Office of the CEO)

Toast•Boston, MA

23h•$160,000 - $256,000•Hybrid

About The Position

Toast is seeking a Director, AI Transformation to lead the company's AI strategy, focusing on integrating AI into daily operations and driving measurable business impact. This role, a top priority for the CEO, involves acting as a strategic advisor to the CEO and senior leadership, managing a team of AI leaders, and directly engaging with functional teams to implement AI solutions. The position requires a unique blend of AI expertise, strategic thinking, coaching abilities, and operational management skills. The day-to-day will involve building enablement tools, coaching teams on AI adoption, and advising on strategic AI investments. The ideal candidate is a hands-on builder, a coach, and an effective operator who can influence stakeholders at all levels.

Requirements

Deep, hands-on AI fluency; ability to build agentic workflows personally.
Strong conceptual and analytical problem-solving skills.
A proven track record of driving change across large, complex organizations.
Experience influencing senior leaders (VP/SVP/C-suite) without formal authority.
Ability to deconstruct ambiguous business processes into structured, actionable parts and execute on them.
Player-coach instinct: ability to make people around you measurably better.
10+ years of experience in consulting, strategy and operations, product, or fast-growth tech.
Exceptional written communication skills, capable of clarifying complex technical topics for non-technical executives.
Proactive, resourceful, comfortable with ambiguity, and able to define the role as it evolves.
High bar on pace and ability to create momentum.

Responsibilities

Own Toast's company-wide AI transformation strategy, including the roadmap from fluency to business impact and the North Star metric for adoption.
Advise the CEO and Chief of Staff on strategic AI initiatives.
Act as a player-coach, building AI capability across all functions by working alongside teams.
Design and build agentic workflows and tools to deliver rapid value to employees.
Collaborate with R&D teams to scope, build, and test platforms that scale AI impact.
Partner with, influence, and hold accountable leaders across SVP and C-suite levels to embed AI into team operations.
Manage the operating rhythm and cultural infrastructure for AI adoption, including enablement cohorts, offsites, and feedback loops.
Track platform spend and usage against budget, modeling the cost of scaling adoption.
Define the future of Toast's AI team and grow from individual contributor to team leader.