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This is the quintessential Vibepiratebay role: purely focused on workflow mapping, prompt engineering, and enablement content.
United States
Full time
Remote
Delivery
Pragmatico helps companies transform the culture around AI so that its use becomes a daily habit, enabling them to achieve productivity gains quickly. We're a values-driven company led by exited founders, already cash-flow positive and well-capitalized. This is your chance to get in on the ground floor to shape how we deliver transformation, grow alongside a rapidly scaling company, and help organizations fundamentally reimagine how they work.
As an AI Tools Specialist & Enablement Lead focused on Microsoft Copilot, you'll be the product knowledge engine that makes AI transformation real for our clients who are deeply embedded in the Microsoft ecosystem. You'll live and breathe Copilot across the full Microsoft 365 suite - Word, Excel, PowerPoint, Outlook, Teams, SharePoint, and beyond - staying ahead of every capability shift, integration update, and feature launch. You'll build and deliver the hands-on, tool-specific training that drives adoption, create scalable content libraries for both employees and executives, and extract best practices from power users. This isn't just a change management or strategy role; this is pure product expertise combined with the ability to make complex tools feel accessible and immediately useful.
This role begins as a contract engagement with a clear path to full-time employment as the company scales.
Why This Role Has Leverage
Live workshops are core to how Pragmatico drives adoption - they create momentum and accountability. But workshops alone are a linear model. Your other leverage in this role is building two content engines that scale delivery far beyond what any workshop calendar can achieve.
The first - aimed at employees doing the work - is a continuously growing library of practical, Copilot-specific content: short videos, prompt libraries, workflow demos, and role-specific use cases showing how Copilot integrates into the Microsoft tools people already use every day. Content that fills gaps between live sessions, reinforces what was taught, and reaches people when they're actually trying to do the thing.
The second - aimed at executives and managers - is leadership-layer content that makes Pragmatico's "leaders before teams" principle stick beyond the initial engagement. Not "here's how to use Copilot in Excel" but "here's how to set expectations, measure adoption, close the gap between Copilot licenses purchased and actual usage, and build AI into how your team operates."
Every workshop you deliver generates raw material. One session becomes five video clips, three prompt templates, a quick-reference guide, and an executive briefing note. That's the multiplier - and it's how this role builds a compounding asset that makes every engagement more valuable than the last.
Responsibilities
Qualifications
Why This Role Matters
This is a founding team role. Most companies buying Copilot licenses are getting a fraction of the value because nobody's showing their people how to actually use it in context. You'll be the person who changes that - who makes a skeptical employee in a workshop think, "Okay, maybe this Copilot thing actually helps me do my job." The voice in the client channel that makes someone feel supported instead of abandoned after training ends. The reason the on-demand library is something people actually open, rather than ignore.
You won't just fill a gap - you'll build a compounding asset that makes every client engagement more valuable than the last. If you're the kind of person who's already deep in Copilot, knows every integration point, and can't stop showing people what you've found, we want to talk.
About 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. Learn more at www.pragmatico.ai/
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.