AI Chief of Staff

Pragmatico

12d

About The Position

This role exists to bridge the gap in mid-market companies where AI adoption has begun but lacks dedicated ownership for full business transformation. The company has already established an AI vision, policy, and foundational training. The Chief of Staff's primary function is to drive the harder, more valuable work of transforming business operations, workflows, and processes using AI. This involves facilitating C-suite ownership, aligning AI strategy with business KPIs, and developing a prioritized roadmap for AI-driven streamlining and redesign. While not performing technical work directly, the role requires staying close to technical execution to translate progress into business value and remove blockers. The position is crucial for scaling Pragmatico's most valuable client service and developing a repeatable playbook.

Requirements

• Experience as a trusted advisor to senior executives, likely in management consulting or professional services.
• Proven ability to facilitate C-suite working sessions effectively.
• Ability to quickly understand a new client's business, including P&L, revenue model, cost structure, top KPIs, and executive team dynamics, across multiple industries.
• Skill in producing executive-grade artifacts suitable for board presentations.
• Experience managing complex engagements where dedicated ownership is lacking.
• Ability to identify business opportunities within client conversations and scope/price new engagements.
• Hands-on AI transformation work within the last few years.
• Daily use of AI tools as core infrastructure, with personal projects and informed opinions on AI effectiveness.
• Experience building a function, practice, or playbook from scratch.

Nice To Haves

• 8-10+ years in consulting or professional services.
• Experience personally sourcing, scoping, and closing expansion revenue through client work.

Responsibilities

• Lead key client relationships and serve as the primary AI advisor to executives.
• Facilitate monthly AI steering committee meetings to align on strategy and roadmap.
• Develop AI transformation roadmaps tied to client business economics, priorities, and KPIs.
• Create board-ready ROI reporting that demonstrates measurable business outcomes from AI transformation.
• Drive progress between meetings by coordinating delivery teams, tracking accountability, clearing blockers, and ensuring owners deliver on commitments.
• Identify and scope new opportunities for Pragmatico within client engagements, contributing to expansion revenue.
• Gather client feedback and insights to inform the development of Pragmatico's products and services.
• Contribute to and refine the AI Chief of Staff playbook.
• Potentially build and lead the AI Chief of Staff function as it grows.

Benefits

• Support from a delivery team including product managers, engineers, adoption and training specialists, and a project manager.
• Opportunity to work directly with a co-CEO.
• Potential for contract engagement or direct full-time employment.
• Flexible work structure.

What This Job Offers

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