AI Tools Specialist & Enablement Lead - Microsoft Copilot

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.

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.

• Build and deliver engaging, tool‑specific workshop content focused on Microsoft Copilot across the full M365 suite, demonstrating real workflows that solve actual pain points for diverse roles and functions in Microsoft‑heavy organizations.
• Stay obsessively current on Microsoft Copilot capabilities, feature releases, integration updates, and best practices across the M365 ecosystem, continuously updating training content to reflect the latest developments. Maintain working familiarity with the broader AI tool ecosystem (Claude, ChatGPT, Gemini, etc.) to provide context on where Copilot fits relative to alternatives and when a complementary tool may be the better answer for a specific use case.
• Create and maintain two distinct content engines: participant‑layer content (how‑to videos, prompt libraries, workflow demos showing Copilot in context within Word, Excel, PowerPoint, Outlook, Teams, SharePoint) and executive‑layer content (leadership guidance on sponsoring and sustaining AI adoption, closing the license‑to‑usage gap).
• Conduct in‑depth power user interviews with the top‑performing employees in client organizations – the people who’ve figured out extraordinary Copilot workflows on their own that would blow their coworkers’ minds if anyone knew about them. Sit with them, watch them work, extract what they’ve built, and package it into compelling peer‑to‑peer content.
• Monitor and respond to client community channels (Teams/Slack), providing expert guidance and troubleshooting…