OverviewPragmatico 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 capability shifts, integration updates, and feature launches. You'll build and deliver 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 role begins as a contract engagement with a clear path to full-time employment as the company scales.Why This Role Has LeverageLive workshops are core to how Pragmatico drives adoption—creating momentum and accountability. But workshops alone are a linear model. Your leverage is building two content engines that scale delivery beyond any workshop calendar.The first engine, 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 use every day. It fills gaps between live sessions, reinforces what was taught, and reaches people when they’re actually trying to do the thing.The second engine, aimed at executives and managers, is leadership-layer content that makes Pragmatico's “leaders before teams” principle stick beyond the initial engagement—helping set expectations, measure adoption, close the license-to-usage gap, and build AI into how teams operate.Every workshop you deliver generates raw material: one session becomes multiple video clips, prompt templates, a quick-reference guide, and an executive briefing note—building a compounding asset that makes every engagement more valuable than the last.ResponsibilitiesBuild 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 update 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 a 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 top-performing employees in client organizations; 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 on Copilot-specific questions while training AI agents to draft quality responses with human-in-the-loop review.Repurpose live workshop material into on-demand content that scales delivery beyond synchronous sessions, building a continuously growing Copilot-specific library that serves current and future clients.Identify and package internal learnings for external content that builds Pragmatico's reputation as the go-to partner for Microsoft Copilot adoption and feeds top-of-funnel marketing efforts.Collaborate with transformation leads to ensure tool-specific training aligns with each client's adoption journey while maintaining deep Copilot product expertise as your primary focus.QualificationsDeep, hands-on expertise with Microsoft Copilot across the M365 suite, with demonstrated ability to leverage its capabilities across diverse business use cases and workflows (including knowing what Copilot does well in Excel vs. where it shines in Teams, and being able to show both in real time).Strong understanding of the Microsoft 365 ecosystem and how organizations actually use it day to day (understanding workflow context, not just the AI layer on top).Obsessive learning habits that keep you current on Copilot developments and the rapidly evolving Microsoft AI roadmap.Natural teacher and communicator who makes complex tools feel accessible to non-technical users without dumbing them down.Engaging presence that can hold a room or a Zoom—live demos with real energy and “try this right now” moments.Content production chops—comfortable creating videos, guides, and demos quickly and at volume.Empathy for skeptical or anxious end users who didn’t ask for this change and need simple, practical solutions for their daily work.Ability to think in terms of content repurposing and scale (every live interaction is raw material for asynchronous content).Comfortable with ambiguity and able to adapt content and delivery as tools evolve and client needs emerge.Entrepreneurial mindset and adaptability to thrive in a fast-moving startup environment where you’ll help define what great enablement looks like.Experience with Claude, ChatGPT, or other AI platforms is a bonus; Microsoft Copilot expertise is the primary requirement.Why This Role MattersThis is a founding team role. Most companies buying Copilot licenses are getting only a fraction of the value because nobody is showing their people how to use it in context. You'll change that—making employees feel like Copilot actually helps them do their jobs, being the voice in client channels that makes people feel supported after training ends, and ensuring the on-demand library is something people open and use.About PragmaticoPragmatico 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 StatementPragmatico 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 protected by applicable law.
