About the rolePragmatico helps companies transform the culture around AI so that its use becomes a daily habit, enabling them to achieve productivity gains quickly. 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 Claude and ChatGPT, you'll be the product knowledge engine that makes AI transformation real for our clients. You'll live and breathe Claude and ChatGPT, staying ahead of every capability shift and feature launch. 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 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 LeverageLive workshops are core to how Pragmatico drives adoption—creating momentum and accountability. In this role, your leverage is building two content engines that scale delivery far beyond what any workshop calendar can achieve.Employee-layer content: a continuously growing library of practical, tool-specific content—short videos, prompt libraries, workflow demos, and role-specific use cases—filling gaps between live sessions and reaching people when they're trying to do the thing.Executive-layer content: leadership-layer content that makes Pragmatico's “leaders before teams” principle stick beyond the initial engagement—guidance on setting expectations, measuring adoption, and building AI into how teams operate.Compounding asset: every workshop you deliver generates raw material (video clips, prompt templates, quick-reference guides, and executive briefing notes), making each engagement more valuable than the last.ResponsibilitiesBuild and deliver engaging, tool-specific workshop content focused on Claude and ChatGPT, demonstrating real workflows that solve actual pain points for diverse roles and functions.Stay obsessively current on Claude and ChatGPT capabilities, feature releases, updates, and best practices; continuously update training content to reflect the latest developments. Maintain working familiarity with the broader AI tool ecosystem (Gemini, NotebookLM, etc.) to provide context on where Claude and ChatGPT fit relative to alternatives.Create and maintain two distinct content engines: participant-layer content (how-to videos, prompt libraries, workflow demos) and executive-layer content (leadership guidance on sponsoring and sustaining AI adoption).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 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 library for current and future clients.Identify and package internal learnings for external content to build Pragmatico's reputation and feed top-of-funnel marketing efforts.Collaborate with transformation leads to ensure tool-specific training aligns with each client's adoption journey while maintaining deep product expertise as your primary focus.QualificationsDeep, hands-on expertise with Claude and ChatGPT, with demonstrated ability to leverage their distinct capabilities across diverse business use cases and workflows.Obsessive learning habits that keep you current on AI tool developments 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—live demos with real energy and “try this right now” moments.Content production chops: comfortable creating videos, guides, and demos quickly and at volume (you’ll be supported, but you need to be able to move).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 the flexibility to adapt content and delivery as tools evolve and client needs emerge.Entrepreneurial mindset with adaptability to thrive in a fast-moving startup environment; you’ll help define what great enablement looks like.Experience with Microsoft Copilot or other enterprise AI platforms is a bonus; Claude and ChatGPT expertise are the primary requirements.Why This Role MattersThis is a founding team role. You'll help make skeptical employees see real value from AI training, provide ongoing support in the client channel after training ends, and ensure 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 uses these tools obsessively and can't stop showing people what you've found, Pragmatico wants to talk.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. Learn more at
www.pragmatico.ai.
