AI Trainer

We're looking for a Trainer to stand at the front of the room and deliver Caravan's flagship product: the in-person, hands-on AI training day. This is the role where our brand becomes real for a customer. Our trainers don't just deliver a fixed script — Caravan is primarily a research organization, and our trainers use their real-world experience and our research to personalize materials to each participant.

Great trainers at Caravan are part teacher, part performer, part coach, and genuinely enthusiastic about the tools they teach.

• Lead at least eight full-day, in-person trainings per month.
• Use Caravan research to tailor lesson plans and exercises for each class.
• Deeply understand the goals and expectations of our customers.
• Drive measurable satisfaction for individuals and organizations.
• Stay up to date on AI applications by building AI tools.
• Contribute to the curriculum so the whole training team gets better.

• A natural teacher & performer: You can hold a room, explain hard things simply, and make people feel capable instead of intimidated. You’re energized, not drained, by a full day in front of learners.
• AI-curious (or obsessed): You’re actively using tools like ChatGPT and Claude in your own work and are excited to go much deeper. You can’t fake the enthusiasm that gets a skeptical room to lean in.
• Adaptive & calm under pressure: You can change the plan mid-session when the room needs something different, troubleshoot a participant’s screen, and keep the energy up.
• Direct & candid: You communicate clearly, give and receive feedback well, and are comfortable with healthy, productive conflict.
• Outcome-obsessed: You care that people change how they work, not just that the day felt good. You take NPS personally.
• Low-ego teammate: You’ll deliver a polished keynote moment one hour and help someone find a menu item the next. You’ll set up chairs and AV without being asked.

There’s no single “right” background, but you might have:

• Experience teaching, training, facilitating, presenting, or coaching adults — formal or informal.
• Hands‑on experience using AI tools in your work, with a point of view about what’s good.
• Strong communication skills and the patience to meet nontechnical learners where they are.
• Comfort in an ambiguous, fast‑changing, startup environment.

• Direct exposure to, and mentorship from, experienced founders and operators.
• A front‑row seat to how AI is changing work, plus daily practice building an AI‑first org.
• Significant scope and the chance to shape both the role and the curriculum as we grow.