AI Chief of Staff

Role Description

Mid-market companies know AI will reshape their business. Few have anyone whose actual job is to make it happen. By the time you step in, the client has already done the early work with Pragmatico: they've set an AI vision, put a usable AI policy in place, and trained their people on GenAI. The culture is ready, and the people are AI-enabled. What comes next is harder and worth more - transforming how the business actually runs, the workflows and the processes, now that everyone can use these tools.

The obstacle is ownership. In a mid-market company, nobody owns AI. The CEO has a hundred priorities, and the CFO, COO, and department heads each see only their slice. No single executive is driving AI across the whole business, so momentum stalls. That's the gap you fill. As AI Chief of Staff, you facilitate that ownership across the C-suite.

About once a month, you bring the senior executives together in what we call the AI steering committee:

• Facilitate and align them on AI strategy.
• Tie it to the business KPIs that actually matter.
• Agree on a prioritized roadmap of business workflows to streamline and redesign with AI.

Between meetings, you do the work that makes it real:

• Meeting with individual executives.
• Pushing workstreams forward.
• Clearing blockers.
• Keeping everyone honest and excited about progress.

You won't need to do the technical work yourself. Our AI operations product managers and AI software engineers handle the execution of workflows and process redesigns. Adoption and training specialists continue to build on the cultural foundation. A project manager supports you on the administrative side. Your job is to hold the container - the relationship, the strategy, and the roadmap - while staying close enough to the technical work that you can translate progress into business value and clear blockers before they stall momentum.

Today, one of our co-CEOs does this for every client. It's the most valuable work we do, and one person can't scale it. You'll take it over, improve it, and build the playbook that lets Pragmatico do it for many more companies.

Qualifications

• Years of experience as a trusted advisor to senior executives, likely in management consulting or professional services.
• Facilitated C-suite working sessions where executives left feeling they had done the work.
• Fluent in a new client's business fast - P&L, revenue model, cost structure, top KPIs, and how the executive team operates.
• Produced executive-grade artifacts that hold up in front of a board.
• Kept complex engagements moving when nobody's getting paid to drive them.
• Heard opportunity in client conversations and scoped and priced it.

Requirements

• 8-10+ years in consulting or professional services, with hands-on AI transformation work in the last few years.
• Personally sourced, scoped, and closed expansion revenue through client work.
• Used AI tools daily as core infrastructure.
• Built something from a blank page before - a function, a practice, a playbook.

Benefits

• Work directly with our co-CEO and shape a service that's still being refined.
• Deep executive relationships, tangible transformation, and clients who become your biggest advocates.
• Flexible engagement structure - can begin as a contract or go straight to full-time.

Company Description

We help mid-market companies become AI-native and win in the AI economy. We were founded by operators who've built and exited companies before, we're well-capitalized, and we lead our clients with culture, change management, and AI adoption because that's what makes AI actually stick.

Equal Opportunity Statement: Pragmatico is an equal opportunity employer, and all qualified applicants will receive consideration for employment without regard to gender, age, race, religion, or any other classification that is protected by applicable law.