Director, AI Transformation (Office of the CEO)

Toast • Boston, MA

1d • 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 partner 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 skills, including hands-on AI building, conceptual thinking, coaching, and operational expertise. The ideal candidate will be adept at understanding complex business processes, automating them with AI, and scaling AI adoption across the organization. The role demands flexibility to shift between strategic advising, hands-on building, and coaching teams.

Requirements

• Deep, hands-on AI fluency, including the 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.
• A player-coach mentality, with a focus on measurably improving the performance of those around them.
• 10+ years of experience in consulting, strategy and operations, product, or a builder role in fast-growth tech.
• Exceptional written communication skills, capable of clarifying complex technical topics for non-technical executives.
• Proactive, resourceful, and comfortable with ambiguity, with a high pace of execution.
• Ability to define the role and create momentum as the position evolves.

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 by working alongside teams and lifting every function.
• Design enablement programs and build agentic workflows and tools to deliver rapid value to employees.
• Collaborate with R&D teams to scope, build, and stress-test platforms that scale AI impact.
• Partner with, influence, and hold accountable leaders across SVP and C-level to embed AI into their teams' operations.
• Manage the operating rhythm and cultural infrastructure for AI adoption, including enablement cohorts, offsites, and shared resources.
• Own the economics of AI transformation, tracking platform spend and usage against budget, and modeling scaling costs.
• Define the future of Toast's AI team and grow from individual contribution to leading the team.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed