AI Tools Specialist & Enablement Lead - Microsoft Copilot

AI Tools Specialist & Enablement Lead - Microsoft Copilot

Location

United States

Employment Type

Full time

Location Type

Remote

Department

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

• 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. Nothing lands like a real person showing another real person what they actually do.

• 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

Qualifications

• Deep, hands-on expertise with Microsoft Copilot across the M365 suite, with demonstrated ability to leverage its capabilities across diverse business use cases and workflows. You should know the difference between what Copilot does well in Excel versus where it shines in Teams, and be able to show people both in real time

• Strong understanding of the Microsoft 365 ecosystem and how organizations actually use it day to day - you understand the workflow context that Copilot plugs into, not just the AI layer on top

• Obsessive learning habits that keep you current on Copilot developments and the rapidly evolving Microsoft AI roadmap without being told to

• 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 - this isn't dry training, it's live demos with real energy and "try this right now" moments

• Content production chops - comfortable creating videos, guides, and demos quickly and at volume (we'll support you, but you need to be able to move)

• Empathy for the skeptical or anxious end user who didn't ask for this change and needs 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 the flexibility to adapt content and delivery as tools evolve and client needs emerge

• Entrepreneurial mindset with the 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, though Microsoft Copilot expertise is the primary requirement

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.