AI Tools Specialist & Enablement Lead - Claude & ChatGPT

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 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 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, tool‑specific content: short videos, prompt libraries, workflow demos, and role‑specific use cases. 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 write a prompt" but "here's how to set expectations, measure adoption, 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 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 updating training content to reflect the latest developments. Maintain working familiarity with the broader AI tool ecosystem (Gemini, Notebook
  
  LM, 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 the top‑performing employees in client organizations – the people who've figured out extraordinary 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 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 that serves current and future clients
• Identify and package internal learnings for external content that builds Pragmatico's reputation 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…