AI Chief of Staff

Pragmatico

Job Overview

Location

United States

Job Type

Full-time

Full Job Description

📋 Description

• As AI Chief of Staff at Pragmatico, you will serve as the trusted executive advisor who drives AI transformation across mid-market companies by aligning C-suite leadership, building actionable roadmaps tied to business KPIs, and ensuring momentum between steering committee meetings—turning vision into measurable operational change.
• Day to day, you will lead client relationships, facilitate monthly AI steering committees with senior executives, coordinate cross-functional delivery teams, track workstream accountability, identify expansion opportunities, and produce board-ready ROI reporting that connects AI initiatives to tangible business outcomes.
• Pragmatico is a well-capitalized, operator-founded company helping mid-market businesses become AI-native through culture, change management, and adoption—where you’ll work directly with a co-CEO to refine and scale a high-impact service that’s currently delivered by a single executive.
• In this role, you will deepen your executive advisory expertise, build a scalable AI Chief of Staff playbook, shape product and service direction from client feedback, and have a clear path to lead and grow this function as it expands across more clients and industries.

🎯 Requirements

• Facilitated C-suite working sessions where executives felt they had done the work and held the room without dominating it.
• Ability to quickly become fluent in a new client’s business model, P&L, cost structure, top KPIs, and executive dynamics across multiple industries.
• Proven ability to produce executive-grade artifacts (e.g., roadmaps, ROI reports) that withstand board-level scrutiny.
• Skill in keeping complex engagements moving forward when no individual is accountable for driving them.
• Talent for spotting expansion opportunities in client conversations and comfortably scoping and pricing new work.

🏖️ Benefits

• Direct reporting and collaboration with a co-CEO, offering high visibility and influence on company strategy.
• Support from a dedicated delivery team (product managers, engineers, adoption specialists, project manager) so you can focus on executive relationships and strategy.
• Flexibility to begin as a contract engagement or transition to full-time based on mutual fit.
• Opportunity to build and lead a growing function, including shaping the AI Chief of Staff playbook and potentially managing a team.
• Exposure to diverse mid-market clients across industries, with chances to see your work featured in case studies, events, and client references.

Skills & Technologies

Senior

Onsite

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Pragmatico

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About Pragmatico

Pragmatico specializes in transforming mid-market companies into AI-native organizations through its unique AI Cultural Transformation System. This system focuses on embedding AI proficiency and adoption into the core culture and employee experience, moving beyond mere technological deployment. Pragmatico addresses the common hurdles of AI change management, skepticism, and lack of sustained usage by aligning leadership, activating employee behaviors with hands-on training and incentives, and making AI adoption permanent and measurable. Their approach emphasizes cultural shifts over technical rollouts, ensuring lasting impact and significant productivity gains. Notably, their proven methodology has led to over 90% active AI adoption across client teams, demonstrating their effectiveness in driving real organizational change.

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