AI Transformation, Enablement

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.

Most of your week is spent in front of a client. The rest is the preparation, follow-up, and relationship management that makes that work effective.

• Run sessions that change how people work. We’re not looking for someone who can simply deliver a polished training. The goal is for people to leave a session able and willing to use AI differently the next day. You’ll design sessions around real work, practical application, and behavior change.

• Show before you tell. A live result lands in a way an explanation never does. You get to the demonstration quickly and make it specific to that client’s actual work. If you can show someone exactly what changes, how much time it saves, or what becomes possible, the value becomes much easier to believe.

• Adapt to the room. Confused rooms need the why before the how. Anxious rooms need smaller steps before they can experiment. Resistant rooms need a credible peer voice before the skills land. You need to be able to read that in real time and adjust your approach without losing the thread of the session.

• Own the client relationship between sessions. You'll be the primary point of contact for your clients. That means staying close enough to understand what's happening inside their business, answering questions as they come up, and helping them work through challenges. This includes keeping adoption moving: recording a short async video when a team needs a refresher, answering questions in a Slack or Teams channel, or following up with a group that has stopped using the tools.
  
  This work is part of owning the outcome, not just delivering the sessions.
  Some of that work will go beyond training. A client may ask for help thinking through where AI fits into their broader strategy, how to approach an AI policy, or how to get a particular team unstuck. You’re not responsible for selling them more work. You’re responsible for being someone they trust to give them a useful answer.
  You’ll also own the day-to-day logistics that come with managing a client relationship, although scheduling is handled for you.

• Stay current on the tools. AI tools evolve constantly. You’ll maintain strong working knowledge of the platforms and capabilities that matter to our clients. When something unfamiliar comes up, you know how to evaluate it quickly rather than bluff your way through it.

• Be the eyes and ears of the field. The patterns you see across clients should make Pragmatico better. You surface what is resonating with clients, what is not, and where audiences get stuck, with enough precision to name what broke down, at what point, and why.

• 3+ years of experience training, teaching, or coaching adults, with executive or senior-leadership audiences specifically. This is not an entry-level facilitation role.

• Experience owning client relationships directly. You’ve been the person in recurring client meetings, kept momentum going between sessions, and built enough trust that clients come directly to you when they need help.

• A track record you can quantify. You can point to specific engagements where you…