The first question is not "contractor or employee." It is "what is finished?" Write the answer as a sentence a stranger could grade. "The support prompt set passes the regression suite at the agreed threshold and the evaluation harness is documented" is a deliverable. "Own our AI stack" is a job.
This distinction matters because the contractor model is built for defined work. Contractors are typically engaged for specialized services, defined projects, or temporary business needs, and a contract can set deadlines, project specifications, and a fixed number of revision rounds up front per Indeed's guide to contracting independent workers. A full-time engineer is the better fit when the work is ongoing and sits at the center of the business.
A practical sorting exercise comes from the startup hiring literature: write every task you currently do on a separate sticky note, group them into categories, and watch roles emerge from the clusters rather than from a job description template according to RBCx's hiring recap. Run that exercise on your AI backlog. The notes that cluster into a one-time project point to a contractor. The notes that keep regenerating every sprint point to a hire.
Three AI work types sort cleanly:
- Prompt work is usually bounded. A prompt audit, a rewrite of a support agent's instructions, and an evaluation suite are all closable scopes. So is a retrieval quality pass on an existing corpus.
- Fine-tuning is bounded only if the dataset is fixed and the success metric is agreed in advance. If the data pipeline is still being built, the scope is really a data engineering project with an unknown end.
- Agents sit in between. A prototype that answers one workflow is a deliverable. An agent that runs in production against real customers and needs monitoring, retries, and guardrails is an ongoing system, and ongoing systems need an owner inside the company.
The trap is scoping a "quick prototype" that turns out to need a production home. Budget for handover from day one, and write the handover into the statement of work as a deliverable, not a courtesy.



