AI Chief of Staff

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: you facilitate and align them on AI strategy, tie it to the business KPIs that actually matter, and 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, and 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.

What You'll Do

Lead our most important client relationships. Step into priority accounts and become the executive these clients trust on everything AI. Run the monthly steering committee. Drive the work between meetings. Be the person the CEO wants in every important conversation.

Turn vision into a roadmap they're excited about. Build AI transformation roadmaps mapped to each client's actual business - their economics, their priorities, the KPIs they're measured on. The kind of plan a CFO walks into a board meeting proud to present. You'll also bring board-ready ROI reporting that ties AI transformation to measurable business outcomes - the kind of proof almost no one in this space can produce, and where Pragmatico is building an industry-leading edge.

Make progress happen between meetings. Keep complex change moving when nobody at the client is getting paid to drive it. Coordinate Pragmatico's delivery team, track accountability across workstreams, follow up without nagging, escalate without burning relationships, and get owners on both sides to actually deliver.

Grow the relationships you lead. As you go deeper, you'll see where Pragmatico can do more, scope that work, and bring it to the client. Our sales team closes it; you're the reason the opportunity exists. The clients you serve become references, speak at our events, and show up in case studies with real business-metric ROI.

Bring the field back to the team. You're our eyes and ears with clients. What you learn shapes our products and services - the AI maturity model, the adoption analytics, the training, the playbook itself.

Build the function, if you want it. You'll sharpen the AI Chief of Staff playbook as you go. For the right person, there's a path to build and lead this function and team as it grows.

Who You Are

You've spent years as a trusted advisor to senior executives, likely in management consulting or professional services, and you're known as the person clients want in the room.

Must-haves

• You've facilitated C-suite working sessions where executives left feeling they had done the work. You hold the room without dominating it.

• You get fluent in a new client's business fast - P&L, revenue model, cost structure, top KPIs, and how the executive team really operates. You've done this across multiple industries.

• You produce executive-grade artifacts that hold up in front of a board.

• You keep complex engagements moving when nobody's getting paid to drive them.

• You hear opportunity in client conversations - the offhand comment that becomes a meaningful new engagement, and you're comfortable scoping and pricing it.

Strong signals you'll thrive here

• 8-10+ years in consulting or professional services, with hands-on AI transformation work in the last few years.

• You've personally sourced, scoped, and closed expansion revenue through your client work, not just been in the room when it happened.

• You use AI tools every day as core infrastructure. You have personal projects you're proud of and real opinions about what's working and what isn't.

• You've built something from a blank page before - a function, a practice, a playbook.

Why Pragmatico

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.

This role sits at the center of how we deliver. You'll work directly with our co-CEO and shape a service that's still being refined. The work compounds: deep executive relationships, tangible transformation, and clients who become your biggest advocates.

The Details

• Reports directly to our co-CEO.

• You'll be supported by a delivery team - product managers, engineers, adoption and training specialists, and a project manager - so you can stay focused on the executive relationships and the strategy.

• We're flexible on how we start. For the right person, this can begin as a contract engagement or go straight to full-time. We'll figure out the structure that works.

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.