Director, AI Transformation (Office of the CEO)

📋 Description

• Own Toast's company-wide AI transformation strategy.
• Coach and scale the org with a player-coach approach.
• Be the hands-on builder, designing enablement and AI workflows.
• Think like a technologist, helping R&D scope and stress-test platforms.
• Manage up, down, and around with SVP/C-level partners.
• Run the operating rhythm and cultural infra to turn energy into practice.

🎯 Requirements

• Deep, hands-on AI fluency with ability to build workflows.
• Track record influencing VP/SVP/C-suite without formal authority.
• Ability to take vague processes and break into actionable parts.
• Player-coach instinct to uplift teams around you.
• 10+ years in consulting, strategy/ops, product, or fast-growing tech.
• Exceptional written communication for non-technical executives.

🎁 Benefits

• Flexible Vacation
• Sabbatical after five years
• Professional Development Reimbursement
• Wellness Stipend
• Peer and company recognition programs
• 401(k) and matching