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Pragmatico

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Pragmatico transforms mid-market companies into AI-native to win in the AI economy. Founded by exited, operational business leaders, the firm guides companies through every stage of AI transformation: AI vision, policy, psychological safety, training/upskilling, and adoption and ROI analytics. Pragmatico's mission is to make AI adoption human, practical, and permanent. 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.

2 open rolesLatest: Jun 15, 2026, 12:00 AM UTC
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AI Chief of Staff

Pragmatico

Pragmatico transforms mid-market companies into AI-native to win in the AI economy. Founded by exited, operational business leaders, the firm guides companies through every stage of AI transformation: AI vision, policy, psychological safety, training/upskilling, and adoption and ROI analytics. Pragmatico's mission is to make AI adoption human, practical, and permanent. 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.

Chief of Staff6 days ago

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.

United States

Client Delivery Coordinator

Pragmatico

Pragmatico transforms mid-market companies into AI-native to win in the AI economy. Founded by exited, operational business leaders, the firm guides companies through every stage of AI transformation: AI vision, policy, psychological safety, training/upskilling, and adoption and ROI analytics. Pragmatico's mission is to make AI adoption human, practical, and permanent. 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.

Role Description As our Client Delivery Coordinator, you'll be the operational backbone of every client engagement. You'll own the workflows, communications, and logistics that keep our delivery running flawlessly, across multiple clients simultaneously, so our strategists and trainers can stay focused on transformation work. This role is fully client-facing, meaning you'll communicate directly with CEOs and executives daily. If you're obsessed with getting the details right, take pride in writing that lands perfectly the first time, and treat fast response times as a personal standard rather than a job requirement, then this role was built for you. This role begins as a contract engagement at 10-15 hours per week, with a clear path to full-time employment as the company scales. Responsibilities - Execute all project tasks completely and on time for every active client engagement, including folder setup, document uploads, email list creation, scheduling, survey workflows, training logistics, and post-session follow-ups. - Own and continuously optimize our Scoro instance, proactively identifying inefficiencies and improving workflows. - Draft and send client-facing communications to CEOs, executives, and working group members. - Manage 20+ concurrent client engagements simultaneously, each at a different stage, with a clear system for tracking what's due, what's dependent on what, and what's coming next. - Maintain accurate, real-time project status across all active engagements. - Respond to client and internal team messages as quickly as possible and no later than four hours. - Coordinate scheduling across clients, ensuring all bundled tasks within each workflow are completed. - Proactively surface timing risks, upcoming deadlines, and anything that needs attention before the delivery team has to ask. Qualifications - Proven track record managing high volumes of concurrent projects or client engagements with documented evidence of complete, on-time execution. - Exceptional written communication skills, specifically for a senior executive audience. - Lightning-fast personal response time standard - you treat four hours as the outer limit, not the target. - Fluency with project management and productivity tools; you build whatever system you need to stay on top of everything. - Extreme attention to detail - you understand that a partially completed workflow is an incomplete workflow. - Comfortable working in a fast-moving startup environment where the playbook is still being built. - Experience communicating directly with C-suite executives. Company Description Pragmatico transforms mid-market companies into AI-native to win in the AI economy. Founded by exited, operational business leaders, the firm guides companies through every stage of AI transformation: AI vision, policy, psychological safety, training/upskilling, and adoption and ROI analytics. Pragmatico's mission is to make AI adoption human, practical, and permanent. 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.

United States
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