Open role
AI Trainer, Services Lead
Full-time · Birmingham, AL
$140k–$160k/yr · Healthcare
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We’re looking for a Services Lead to own Caravan’s recurring relationships with clients: the ongoing engagements that pick up where a training day ends. This is a delivery-first, hands-on role: you won’t just coordinate the work; you will be responsible for executing the deliverables yourself. You’ll project-manage each retainer, keep the work on track, and personally produce the high-quality outputs that clients come to trust. You own whether the work gets delivered, gets delivered well, and keeps getting renewed. As the line grows, so does the seat.
What you'll do
- Own and execute the end-to-end delivery of Caravan’s recurring retainer engagements: from project management to the creation of the deliverables themselves.
- Maintain a high bar for craft: you are expected to do the actual work (drafting guides, building AI workflows, and conducting follow-up sessions) not just manage a timeline.
- Be the trusted point of contact for retainer clients.
- Drive renewals and organic growth by making clients measurably successful.
- Act as the primary practitioner for retainer clients, collaborating with trainers and engineers when specialized support is needed.
- Help shape the retainer offering — how it’s scoped, priced, and run — as the line matures.
Who you are
- An owner & operator: You take responsibility for outcomes, not just tasks. When something’s slipping, you’ve already moved on it.
- A natural project manager: You bring order to multiple moving engagements, keep the right people informed, and never let a ball drop in the handoffs.
- Client-trusted: You build calm, durable relationships. Clients feel taken care of, and they come back.
- AI-curious (or obsessed): You’re actively using tools like ChatGPT and Claude and are excited to go deeper — both to run your own work better and to speak credibly with clients about what we build.
- Direct & candid: You communicate clearly, give and receive feedback well, and are comfortable with healthy, productive conflict.
- Low-ego teammate: You’ll present a renewal plan one hour and chase down a missing deliverable the next. You do what the engagement needs.
Qualifications
There’s no single “right” background, but you might have:
- Experience owning client relationships, accounts, or engagements end-to-end: services, consulting, customer success, or account management.
- Demonstrated project-management chops across multiple concurrent workstreams.
- Hands-on experience using AI tools in your own work, with curiosity to go further.
- Strong writing and communication skills, and the instinct to over-communicate with clients.
- Comfort in an ambiguous, fast-changing, startup environment.
What you'll get
- 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 service line as we grow.
If you're not sure you meet all the criteria but this sounds like your kind of job, you should strongly consider applying.
Ready to apply?
The application is a few short questions — about five minutes. We read every one.