AI Transformation, Enablement

Pragmatico
Remote

About The Position

Mid-market companies are investing in AI, but most are still struggling to turn that investment into day-to-day behavior change. They run pilots, roll out tools, and train their teams, but too often people leave a session informed and then open their laptop the next day exactly the same way they always have. Knowing about AI is not the same as using it. This role exists to close that gap. You’ll start with leaders, helping the C-suite become confident, credible users themselves, then work across the organization to build real adoption. We’ll know it’s working when people are using AI regularly and clients can point to measurable business results.

Requirements

  • 3+ years of experience training, teaching, or coaching adults, with executive or senior-leadership audiences specifically.
  • Experience owning client relationships directly, including recurring meetings, maintaining momentum, and building trust.
  • A quantifiable track record of moving groups from resistant or skeptical to actively adopting new tools, processes, or behaviors, with metrics to prove it.
  • Hands-on experience using AI in your own work, demonstrating practical application.
  • Comfort being challenged live by a skeptical executive without a script.

Responsibilities

  • Run sessions that change how people work, designing sessions around real work, practical application, and behavior change.
  • Show before you tell by quickly demonstrating live results specific to the client's work.
  • Adapt to the room by adjusting approach in real-time based on audience engagement and needs.
  • Own the client relationship between sessions, acting as the primary point of contact, staying close to their business, answering questions, and helping them work through challenges.
  • Keep adoption moving by providing refreshers, answering questions in communication channels, and following up with groups.
  • Assist clients with strategic thinking about AI integration, AI policy, and overcoming specific team challenges.
  • Manage day-to-day logistics of client relationships.
  • Stay current on AI tools and capabilities relevant to clients, evaluating new tools quickly.
  • Surface insights from client interactions to improve Pragmatico's offerings, identifying what resonates, what doesn't, and where audiences get stuck.
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